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3 Oct - 4 Oct
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4 Oct - 5 Oct
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9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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Our top choices for Shelter Island hotels

A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.

1. Sound View Greenport

Sound View Greenport
Greenport
Guest highlights
  • Complimentary spread by the pool
  • Good continental breakfast included
  • Beautiful sound view from rooms
€220
includes taxes & fees
2 Nov - 3 Nov
Sound View Greenport
An outdoor patio area with string lights, tables, chairs, and a fire pit.
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.
A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.
A large, white building with multiple windows and a prominent tree in the foreground.

2. The Chequit

The Chequit
The Heights
€152
includes taxes & fees
1 Nov - 2 Nov
The Chequit
A deck with outdoor seating, overlooking a body of water with a sunset view.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
Room
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

3. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
Guest highlights
  • Stunning views of the coastline
  • Unique and inviting hotel location
  • Beautiful swimming pool for guests
The Pridwin Hotel
A two-story house with a balcony, outdoor seating area, and a variety of plants.
A bar area with stools, a shelf with glasses, and decorative plants.
A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.
A restaurant with a signboard listing its hours of operation.

4. Zey Hotel

Zey Hotel
Greenport
Guest highlights
  • Soft, supportive mattresses
  • Ample on-site parking space
  • Friendly and helpful staff
€171
includes taxes & fees
5 Oct - 6 Oct
Zey Hotel
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A storefront with a sign reading "THE SHOALS".
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

5. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
Guest highlights
  • Beautiful property on the water
  • Waking up to the view of Peconic Bay
  • Fresh coffee and tea for guests
€227
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A swimming pool with a wooden deck, lounge chairs, and a fence.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A reception desk with a sign that reads 'The Harbor Front Inn.' There are potted plants and a lamp on the desk.

6. The Harbor Front Inn

The Harbor Front Inn
Greenport
Guest highlights
  • Fresh breakfast to start the day
  • Beautiful balcony rooms facing the harbor
  • Incredible views of the landscape
€189
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A grassy area with trees and a view of a body of water.
A bedroom with a large bed, a desk, a chair, and a view of the outdoors.

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
Guest highlights
  • Beautiful location steps from the beach
  • Very helpful and friendly staff
  • Delicious food at on-site restaurant
€330
includes taxes & fees
12 Oct - 13 Oct
Silver Sands Motel & Beach Bungalows
Terrace/patio
Room
Living area
Room

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
Guest highlights
  • Near Greenport Carousel
  • Beautiful view of the water
  • Swimming pool for guests to enjoy
€270
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A spacious hallway with high ceilings, arched columns, and chandeliers.
A garden pathway with a fence, illuminated by string lights, leading to a building.
A large, historic building with multiple stories and a prominent tower, surrounded by lush greenery and a body of water.
A modern indoor swimming pool with marble walls and a tiled floor.

9. Montauk Manor

Montauk Manor
Montauk
Guest highlights
  • Clean pool with hot tub
  • Beautifully maintained grounds and property
  • Excellent on-site restaurant options
€145
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.
A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.
A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.
A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

10. The Menhaden

The Menhaden
Greenport
Guest highlights
  • Steps from Greenport Carousel
  • Exceptional staff responsiveness and care
  • Gorgeous brand new property
€386
includes taxes & fees
1 Nov - 2 Nov
The Menhaden
A bedroom with a bed, bedside tables, a lamp, a window, and a door.
A living room with a beige sofa, a coffee table, and a dining table set with plates and glasses.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.
A beach with a wooden walkway along the shore, calm water, and a sunset sky.

11. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
Guest highlights
  • Easy ferry access to nearby islands
  • Lovely rooms with space to unwind
  • Great condition of the guest house
West Neck Guesthouse
Front of property – evening/night
Bar (on property)
Terrace/patio
Property amenity

12. Shelter Island House

Shelter Island House
Shelter Island Heights
€204
includes taxes & fees
5 Oct - 6 Oct
Shelter Island House
A wooden pathway leading to a beach with a view of the ocean.
An indoor swimming pool with a view of the beach, lounge chairs, and large windows.
A house with a stone wall and a garden with various plants and flowers.
A beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.

13. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
Guest highlights
  • Beautiful ocean view
  • Delicious food made with fresh ingredients
  • Excellent service from staff
€475
includes taxes & fees
3 Nov - 4 Nov
Gurney's Montauk Resort & Seawater Spa
A modern outdoor lounge area with a long bench and cushioned seating, a central fire feature, and glass walls offering views of the interior.
A modern outdoor seating area with a glass fire feature and a striped sofa.
A bar area with a high bar counter, stools, and a fireplace.
A couple sitting on a striped sofa with a fire feature in the center.

14. Hilton Mystic

Hilton Mystic
Mystic
Guest highlights
  • Large and clean pool area
  • Delicious breakfast to start the day
  • On-site restaurant for dinner
€149
includes taxes & fees
1 Nov - 2 Nov
Hilton Mystic
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.
A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.
An outdoor dining area with tables and chairs, string lights, and hanging lanterns.
A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

15. American Beech Hotel

American Beech Hotel
Greenport
Guest highlights
  • On-site restaurant for convenient dining
  • Picnic basket breakfast delivered
€290
includes taxes & fees
5 Oct - 6 Oct
American Beech Hotel
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A dining area with a round table, chairs, a vase, and a painting on the wall.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

16. Oyster Estate

Oyster Estate
Greenport
Guest highlights
  • Beautiful pool and hot tub area
  • Consistent daily housekeeping service
  • Easy on-site parking available
€291
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

17. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
Guest highlights
  • Hearty breakfast before heading out
  • Lovely swimming pool for guests
  • Charming garden rooms with character
€457
includes taxes & fees
2 Nov - 3 Nov
Faraway Sag Harbor
A beach with a sunset, calm water, and scattered rocks.
A large wooden building with multiple windows and a sloped roof.
A neatly made bed with floral bedding, a bedside table with a lamp, and a breakfast tray with fruits and a pitcher.
A wooden staircase with a lamp, a floral armchair, and a large window with curtains.

18. Arbor View House B&B

Arbor View House B&B
East Marion
Guest highlights
  • Meticulously clean and spotlessly maintained
  • Generous breakfast to start the day
Arbor View House B&B
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

19. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
Guest highlights
  • Plenty of free parking available
  • Nice continental breakfast options
  • Waterfront view from the deck
€222
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A modern kitchen area with a blue island, wooden accents, and a sign that reads "Delight in the day."
An aerial view of a residential area with a large building, a parking lot, and a lake in the background.
A modern reception area with a wooden reception desk, a green artificial grass rug, and a large abstract wall art piece.
A modern lounge area with seating, a flat-screen TV, and a large window with curtains.

20. Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton
Mystic
Guest highlights
  • Pool area with lounge chairs
  • Free Continental breakfast options
  • Easy parking for arriving guests
€108
includes taxes & fees
2 Nov - 3 Nov
Spark by Hilton Mystic Groton
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Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most.
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming area features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The area provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

Coecles Harbour offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island area balances authentic maritime character with holiday amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes centre stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack.

Stay near popular Shelter Island attractions

A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
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A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
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Mashomack Preserve

Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.
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Gardiner's Bay Country Club

This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbour. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.
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Shelter Island Historical Society

8.0/10 (1 review)
This historic museum preserves Shelter Island's maritime heritage through artefacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.
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Menhadden Lane Beach

8.8/10 (3 reviews)
This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.
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Havens House

Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.
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Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
A coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"Our stay was impressive. We hadn't expected how comfortable and roomy the suite was. The whirlpool bath was like a small swimming pool and the room was large enough to have a party."
Neil 1-night trip
Posted 12 hours ago
Zey Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Melanie 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa
Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"I am very positive on Montauk Blue for a great location right on the beach, a 3 minute walk to the village and excellent service by staff. Couldn’t be better and I have stayed at other Montauk locations."
Steven 2-night trip
Posted 1 day ago
Montauk Blue Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Kind of expected to be disappointed. However, really delighted. Room was lovely, clean and thoughtful appointments. Location was OK, but doable."
Randi 2-night trip
Posted 1 day ago
The Bentley Hotel Southampton
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Nice place !"
Donald 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Such a great spot! Clean, easy access, everything you need!!"
Christian 3-night trip
Posted 2 days ago
Ocean Resort Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 3 days ago
Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"it was a good experience."
Jinwoo 1-night trip
Posted 4 days ago
Montauk Yacht Club

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
€80
5 Oct - 6 Oct
includes taxes & fees
8/10 Very good! (1,002 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
€90
5 Oct - 6 Oct
includes taxes & fees
6.8/10 (893 reviews)
Budget Host East End
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
€113
28 Oct - 29 Oct
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
€146
12 Oct - 13 Oct
includes taxes & fees
9.6/10 Exceptional! (593 reviews)
The Bentley Hotel Southampton
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
€149
18 Oct - 19 Oct
includes taxes & fees
Ocean Surf Resort
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
€215
13 Oct - 14 Oct
includes taxes & fees
The Hampton Maid

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island boasts beautiful beaches like Sunset Beach, perfect for relaxation and picturesque views.
  • Outdoor Adventures: Enjoy activities such as kayaking, golfing, and exploring local parks that highlight the island's natural beauty.
  • Rich History: Visit the Shelter Island Historical Society to learn about the area's heritage and cultural significance.
  • Romantic Getaways: The island offers idyllic settings for couples seeking a romantic escape amidst tranquil surroundings.
  • Diverse Accommodation: Choose from charming bed and breakfasts to intimate inns, catering to all tastes and preferences.

Find great hotels near Shelter Island

Discover the charm of Shelter Island, where a variety of accommodation options await you. From quaint bed and breakfasts to intimate inns, there’s something for every traveller. Emphasising pet-friendly amenities and adventure-filled family experiences, these lodgings provide a warm welcome. Whether you choose a guest house or the renowned Shelter Island House, you'll find comfort and convenience in this picturesque destination.

  • Sound View Greenport: This 3.5-star hotel offers a delightful beach getaway with a family-friendly atmosphere. Located 6.4km from Shelter Island, Sound View Greenport is particularly suitable for travellers seeking a blend of leisure and business travel experiences. Guests appreciate the direct access to the beach, allowing for sun-soaked days by the water. The property is equipped with amenities for children, including complimentary cribs and window guards, ensuring a safe environment for families. With its inviting ambiance and essential services, it stands out as an excellent choice for those looking to unwind by the coast.
  • Stirling House Bed & Breakfast: This charming 3-star bed and breakfast is situated a mere 4.8km from Shelter Island and boasts an impressive guest rating of 9.8 out of 10. Stirling House offers a warm, homely atmosphere, complete with complimentary full breakfast options and a relaxed bar and lounge area. For those looking to explore the local area, bicycle rentals are conveniently available nearby. Guests can enjoy various entertainment options, including a DVD player and premium television channels, as well as stunning views of the waterfront and bay, making it an idyllic retreat for those who appreciate a personalised touch.
  • Sag Harbor Inn: Located 8.0km from Shelter Island, Sag Harbor Inn is a well-rated 3.5-star hotel that caters to business travellers. With a guest rating of 9.4 out of 10, this inn combines comfort and convenience. The property is designed to meet the needs of those travelling for work, while still providing a pleasant and relaxing environment. Its strategic location allows guests easy access to local amenities and attractions, making it an excellent base for exploring the charming town of Sag Harbor.

Where to stay near Shelter Island

Embarking on a vacation to Shelter Island offers a delightful blend of outdoor adventures and romantic beach escapes. Explore the charming streets of Shelter Island, bask in the stunning views at Sunset Beach, and discover the rich history that permeates this scenic locale. Just a stone's throw away, Long Island presents family-friendly excursions and luxurious experiences, ensuring a memorable holiday filled with diverse atmospheres and picturesque surroundings.

  • Greenport: Positioned a mere 4.8km from Shelter Island, Greenport is a charming city that offers a delightful mix of outdoor and romantic experiences. This coastal gem sees a moderate flow of travellers, particularly from June to August when visitors flock to enjoy its pristine beaches and recreational areas. One of the highlights of Greenport is its vibrant music scene, with concerts taking place throughout the summer. Golf enthusiasts will also appreciate the local golf course, while families can spend quality time at the nearby parks and beaches, making it an ideal destination for a relaxed getaway.
  • Springs: Located 16.1km from Shelter Island, Springs is a picturesque village that welcomes visitors year-round, with peak arrivals occurring from September to November. Known for its family-friendly atmosphere, Springs is a fantastic spot for those seeking outdoor activities. The village boasts beautiful beaches and parks, providing ample opportunities for picnicking and recreational fun. Golfing is a popular pastime here, with excellent courses available for enthusiasts. Springs offers a laid-back vibe, making it perfect for families wishing to escape the hustle and bustle.
  • Hamptons: Just 14.5km from Shelter Island, the Hamptons are a world-renowned playground for those seeking beachside leisure and outdoor adventures. This area experiences a moderate influx of visitors, particularly during the summer months from June to August. Besides its stunning beaches, families can enjoy scenic lakes and picturesque parks. The Hamptons are also home to excellent golf courses and opportunities for skiing in the winter months. The romantic ambiance and vibrant local culture make the Hamptons an enticing destination for couples and families alike.

Things to do near Shelter Island

Shopping

Discover local shops on Shelter Island offering unique gifts and souvenirs, including artisanal crafts and beach-themed items. If you're up for a drive, visit the nearby Hamptons, approximately 19.3km away, where you can explore larger boutiques and high-end shops in a charming coastal setting.

Recreation

At the Shelter Island Meditation Center, you can immerse yourself in serene surroundings while participating in guided meditations and mindfulness workshops. The Spa at the Chequit offers rejuvenating treatments, including massages and facials, utilising local ingredients to enhance relaxation and well-being.

Adventure

Experience the thrilling atmosphere at Riverhead Raceway, located 35.4km from Shelter Island, where you can witness exciting motor racing events. Alternatively, head to Waterford Speedbowl, situated 38.6km away, to enjoy competitive racing in a vibrant setting filled with adrenaline and excitement.

Nightlife

Shelter Island offers a charming nightlife with venues like The Tavern, known for its laid-back atmosphere and live music, and Sunset Beach, where you can enjoy cocktails by the water. Explore local bars and enjoy a relaxed evening with friends in this picturesque setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shelter Island

To save money on your trip to Shelter Island, plan your visit between January and March when hotel prices are at their lowest, especially on Tuesdays. Avoid weekends, particularly Saturdays, for more affordable rates. Use Expedia to refine your accommodation options by budget and preferences, and consider eco-certified hotels for sustainability. Additionally, look for package deals that combine flights and activities with your hotel booking for extra savings. Take advantage of free activities available on the island to enhance your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation that suits you best. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To discover the most affordable prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Shelter Island

Shelter Island offers a perfect blend of outdoor adventures and romantic beach getaways. Visitors can explore stunning beaches, charming urban parks, and historic buildings that reflect the island's rich culture. Key attractions include the Shelter Island Historical Society, which provides insights into the area's heritage. Whether you're seeking relaxation or outdoor experiences, Shelter Island caters to all tastes, making it an ideal destination for travellers from Ireland.

  • Gardiner's Bay Country Club: Nestled within Shelter Island, this golf club offers a serene environment for golf enthusiasts. The lush greens and well-maintained fairways provide a picturesque setting, making it an ideal spot for a leisurely round of golf amidst stunning views of Gardiner's Bay.
  • Shell Beach: Enjoy the relaxed beach vibes at Shell Beach, where you can unwind on the sandy shores, collect unique shells, or take a refreshing swim in the clear waters. This tranquil beach is perfect for a peaceful day by the sea, surrounded by natural beauty.
  • Mashomack Preserve: This urban park is a haven for nature lovers and families alike. With its scenic trails and diverse wildlife, Mashomack Preserve invites you to explore the outdoors, offering opportunities for hiking and picnicking in a serene environment.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

The nearest major airports for your trip to Shelter Island

Reaching Shelter Island is convenient via several major airports. Bradley International Airport (BDL) in Hartford, CT, is located 99.8km away, with nearby accommodations like the 3-star Capitol Hotel and Candlewood Suites Windsor Locks, both offering easy access to the airport. John F. Kennedy International Airport (JFK) is 130.4km distant, featuring luxurious options such as The William Vale and Graduate by Hilton, both within 19.3km. LaGuardia Airport (LGA) is slightly farther at 133.6km, with high-end hotels like Four Seasons Hotel New York and The Lowell located just 8.0km away, providing transport services for guests.

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 15.5 mi (24.9 km) from the heart of Shelter Island, Pier Blue Inn Old Saybrook - Essex is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Gurney's Montauk Resort & Seawater Spa and Offshore Montauk. See all available top hotels, or vacation rentals in Shelter Island.
What are some of the best holiday rentals that Shelter Island has to offer?
Unobstructed Ocean Views ! A Beautiful Montauk Getaway: This holiday home rental outside of Shelter Island is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden. See all vacation rentals in Shelter Island.
If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.
What's the best dog-friendly accommodation option in Shelter Island?
Sunset Beach Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.
What's the best hotel to stay near the beach in Shelter Island?
Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach . See more stays near the beach in Shelter Island.
What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk and Water's Edge Resort & Spa are a couple of other choices that offer an on-site pool. View all hotels with pools in Shelter Island.
What's it like to stay in Shelter Island?
Visitors can enjoy all that Shelter Island has to offer, including the parks, beaches and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 101 hotels and other accommodation options to choose from. Find out more about Shelter Island.
What should I see while I'm in Shelter Island?
Natural beauty is on display at Mashomack Preserve, Sunset Beach and Wades Beach. A couple of additional sights to add to your itinerary are Shelter Island Historical Society and Crescent Beach. Take a look at what more there is to see and do in Expedia's Shelter Island guide.
What's the seasonal weather in Shelter Island?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.

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