Shelter Island Hotels

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Top 10 trending Shelter Island hotels

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is €154
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very good, (691)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
The price is €309
includes taxes & fees
4 Dec - 5 Dec
Gurney's Montauk Resort & Seawater Spa

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.4 out of 10, Exceptional, (1005)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is €263
includes taxes & fees
30 Nov - 1 Dec
Saybrook Point Resort & Marina

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (67)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main

Pier Blue Inn Old Saybrook - Essex

2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1000)
"Always a great stay at Pier Blue. Comfy bed and plenty of room."
United States
Patricia
Pier Blue Inn Old Saybrook - Essex

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1005)
"We love the stay everything was perfect"
United States
angelica
The price is €174
includes taxes & fees
2 Dec - 3 Dec
Water's Edge Resort & Spa

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (970)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
The Atlantic Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (289)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (337)
"Staff and hotel are lovely "
United States
Steven
The price is €244
includes taxes & fees
30 Nov - 1 Dec
Madison Beach Hotel

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1008)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is €100
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Old Saybrook - Westbrook

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is €145
includes taxes & fees
21 Dec - 22 Dec
The Harbor Front Inn

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (69)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is €130
includes taxes & fees
3 Dec - 4 Dec
Offshore Montauk

The Hampton Maid

2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (683)
"Was so lovely would definitely come back again, very cute clean and safe "
United Kingdom
Maria
The Hampton Maid

The Preston House & Hotel

3.5 star property
Riverhead
9.8 out of 10, Exceptional, (368)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is €185
includes taxes & fees
1 Dec - 2 Dec
The Preston House & Hotel

Marram

4.0 star property
Montauk
8.8 out of 10, Excellent, (249)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
The price is €327
includes taxes & fees
26 Nov - 27 Nov
Marram

Sag Harbor Inn

3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (569)
"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "
United States
Lori
The price is €186
includes taxes & fees
25 Nov - 26 Nov
Sag Harbor Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (437)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is €115
includes taxes & fees
21 Nov - 22 Nov
Hamlet Inn

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (382)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is €119
includes taxes & fees
27 Nov - 28 Nov
The Bentley Hotel Southampton

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (593)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is €201
includes taxes & fees
23 Nov - 24 Nov
Sound View Greenport

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (207)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is €203
includes taxes & fees
23 Nov - 24 Nov
The Sagaponack
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Shelter Island Historical Society and Sunset Beach.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Stay near popular Shelter Island attractions

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.

Central Park summer

Top Shelter Island Hotel Reviews

More cheap stays in Shelter Island

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island boasts beautiful beaches ideal for relaxation, sunbathing, and beach activities.
  • Charming Scenery: The picturesque landscape offers a tranquil atmosphere, perfect for romantic getaways.
  • Historic Exploration: Discover the rich history of the area through its historic buildings and local culture.
  • Outdoor Activities: Engage in scenic golf courses, beach firepits, and various outdoor adventures.
  • Family-Friendly Accommodations: A range of lodging options ensures comfort and accessibility for all guests.

Find great hotels near Shelter Island

Whether you're seeking a charming agritourism property or a comfortable hotel, Shelter Island offers a delightful array of lodging options to enhance your holiday experience. With a focus on family-friendly amenities and pet-friendly policies, you'll find accommodations that cater to your every need, including accessible rooms and air-conditioned seating. Explore the beautiful surroundings and enjoy a memorable stay in this picturesque destination.

  • Sound View Greenport: Nestled a mere 6.4km from Shelter Island, Sound View Greenport caters to the discerning traveller seeking a blend of business and leisure. This 3.5-star hotel is positioned directly on the beach, providing guests with stunning seaside views and easy access to sun-soaked relaxation. Families will appreciate the child-friendly amenities, including complimentary cribs and window guards for safety. Business travellers can take advantage of the well-equipped conference space and meeting rooms, making it an ideal spot for both work and play.
  • Sag Harbor Inn: Located 8.0km from Shelter Island, Sag Harbor Inn is another excellent choice for those looking to combine business with leisure. This 3.5-star accommodation is tailored for the business-minded traveller, featuring dedicated meeting rooms for your professional needs. While its focus is on business, guests can also enjoy the charming surroundings of Sag Harbour, offering a quintessential seaside experience. The inn’s warm atmosphere ensures a comfortable stay, making it a practical choice for your visit.
  • The Harbor Front Inn: Just 4.8km from Shelter Island, The Harbor Front Inn offers a unique appeal for those travelling with pets, as it is a pet-friendly establishment. This 3.5-star hotel combines business amenities with a welcoming environment for furry friends, allowing pets in rooms and waiving fees for service animals. Ideal for both business and leisure travellers, the inn provides a comfortable retreat while being close to the picturesque waterfront, enhancing your stay with an inviting atmosphere and modern amenities.

Where to stay near Shelter Island

Shelter Island offers a delightful blend of stunning beaches and charming scenery, perfect for a romantic or relaxing getaway. With easy access to lovely beaches, visitors can unwind and soak up the sun. Explore nearby towns for family-friendly excursions and budget-friendly activities that showcase the area's rich history and natural beauty. Whether you're strolling along the shoreline or enjoying a scenic drive, Shelter Island promises a memorable experience for every traveller.

  • Hamptons: A mere 14.5km from Shelter Island, the Hamptons are a quintessential summer retreat, famed for their beautiful beaches and vibrant outdoor lifestyle. Visitors flock here from June to August for romantic getaways and family outings. The area boasts an array of golf courses, music concerts, and luxurious resorts, catering to diverse tastes. Local highlights include pristine beaches and serene lakes, making it an ideal spot for relaxation and outdoor activities. The Hamptons’ charming villages exude a sophisticated yet laid-back vibe, perfect for leisurely strolls and scenic picnics.
  • Greenport: Located just 4.8km from Shelter Island, Greenport is a delightful coastal village that welcomes visitors with its quaint charm and rich maritime history. The peak travel season runs from June to August, attracting couples and families seeking beachside fun and outdoor adventures. Popular activities include golfing and attending local music concerts, while the nearby family-friendly beaches provide ample opportunities for sunbathing and swimming. Greenport also features a vibrant event conference venue, adding to its appeal as a cultural hub. The picturesque waterfront and charming shops make for a perfect day of exploration.
  • Sag Harbor: A short 8.0km jaunt from Shelter Island, Sag Harbor is a historic whaling village that combines scenic beauty with a rich cultural heritage. The area draws visitors from June to August looking for outdoor activities and romantic seaside experiences. With access to golf courses and ski fields, it offers a variety of recreational options. Nearby beaches and parks provide tranquil spaces for relaxation or picnicking. Sag Harbor's quaint streets are lined with boutiques and galleries, making it a delightful spot for leisurely exploration and discovering local art.

Things to do in and around Shelter Island

Shelter Island offers a delightful blend of outdoor and beach activities perfect for romantic getaways. Visitors can enjoy scenic golf courses, engaging acoustic sets, and memorable beach days. Relax by the water, partake in various beach activities, or gather around beach firepits for a cosy evening. Whether you're seeking adventure or tranquillity, Shelter Island provides an idyllic setting for a rejuvenating holiday.

Shopping

The Greenport Farmers' Market is a charming spot located 4.8km away, offering local produce and unique gifts. The Style Bar, 8.0km from Shelter Island, features trendy clothing and accessories. If you're up for a drive, visit Love Lane, 17.7km away, known for its family-friendly shops and boutiques.

Recreation

At Shelter Island Whale's Tail, enjoy a fun-filled mini-golf experience with family vibes and adventure. For a more serene outing, visit Cedar Point County Park, where you can relax amidst nature's beauty, and indulge in outdoor sports at Noyac Golf Club, roughly 9.7km away.

Adventure

At Splish Splash Water Park, 37.0km from Shelter Island, enjoy thrilling water rides and family-friendly attractions. Discover the stunning scenery along the Walking Dunes Trailhead, located 25.7km away, perfect for adventurous hikes. For adrenaline junkies, 35.4km away, Riverhead Raceway offers exciting motor racing experiences.

Nightlife

The nightlife on Shelter Island offers a charming mix of outdoor fun at the Greenport Carousel, just 4.8km away, and cultural experiences at Bay Street Theatre, 8.0km away. For a romantic film night, visit Regal UA East Hampton, located 17.7km from the island.

*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 and around Shelter Island

Shelter Island, a charming destination for outdoor and romantic getaways, offers a delightful mix of beaches, historic buildings, and urban parks. Visitors can immerse themselves in the local culture while enjoying family-friendly experiences. With its picturesque landscape and tranquil atmosphere, Shelter Island is perfect for those seeking relaxation by the shore or exploring the rich history of the area.

  • 67 Steps Beach: Located 6.4km from Shelter Island, 67 Steps Beach offers a serene escape with stunning views and relaxing beach vibes. Enjoy the soft sands and gentle waves, making it an ideal spot for sunbathing or leisurely strolls along the shore.
  • Gardiner's Bay Country Club: Situated within Shelter Island, Gardiner's Bay Country Club is a golfer's paradise. This picturesque course offers challenging play amidst beautiful landscapes, perfect for both seasoned golfers and beginners looking to enjoy a day on the greens.
  • Orient Point County Park: Just 12.9km away, Orient Point County Park is a family-friendly urban park that invites outdoor activities. Experience picnic areas, walking trails, and scenic views, making it a wonderful destination for a day out in nature.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependant 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

For your visit to Shelter Island, you have several airport options. Islip, NY (ISP-MacArthur) is located 70.8km away, with nearby hotels such as the 3.5-star Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 6.4km from the airport. New Haven, CT (HVN-Tweed) is closer at 51.5km, offering quality accommodations like the 4-star Blake Hotel and Graduate by Hilton, both just 4.8km from the airport. The nearest option is East Hampton, NY (HTO), situated 14.5km away, where you can find the luxurious Mill House Inn and Topping Rose House, both 4.8km from the airport, providing easy access to your destination.

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 18.4 mi (29.7 km) from the heart of Shelter Island, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Pier Blue Inn Old Saybrook - Essex and Montauk Blue Hotel. 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?
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available: This holiday home rental outside of Shelter Island is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. 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. Features a seasonal outdoor pool, an indoor pool and a private beach. Montauk Blue Hotel and Quality Inn Old Saybrook - Westbrook 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 95 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 Sunset Beach, Mashomack Preserve and Crescent Beach. A couple of additional sights to add to your itinerary are Gardiner's Bay Country Club and Shelter Island Historical Society. 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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