A calm lake with a forest in the background during sunset.

Southold Hotels

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Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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Our top choices for Southold hotels

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Maria
€306
includes taxes & fees
1 Sept - 2 Sept
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Suzanne
€319
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport

3. Zey Hotel

Zey Hotel
Greenport
United States
shaun
€198
includes taxes & fees
30 Aug - 31 Aug
Zey Hotel

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
John
€314
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn

5. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
€240
includes taxes & fees
8 Sept - 9 Sept
House on Chase Creek

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
€386
includes taxes & fees
21 Sept - 22 Sept
Silver Sands Motel & Beach Bungalows

7. The Chequit

The Chequit
The Heights
United States
Kathleen
€286
includes taxes & fees
8 Sept - 9 Sept
The Chequit

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
€372
includes taxes & fees
21 Sept - 22 Sept
Cliffside Resort Condominiums

9. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
€314
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort

10. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
€578
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel

11. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Egor
€82
includes taxes & fees
27 Aug - 28 Aug
Pier Blue Inn Old Saybrook - Essex

12. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
€352
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

13. Clinton Motel

Clinton Motel
Clinton
United States
Selena
€78
includes taxes & fees
2 Sept - 3 Sept
Clinton Motel

14. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
€188
includes taxes & fees
16 Sept - 17 Sept
The Bentley Hotel Southampton

15. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
United States
Sally
€185
includes taxes & fees
13 Sept - 14 Sept
Ocean View Terrace Inn

16. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
€309
includes taxes & fees
31 Aug - 1 Sept
Shelter Island House

17. American Beech Hotel

American Beech Hotel
Greenport
United States
kerri
€397
includes taxes & fees
8 Sept - 9 Sept
American Beech Hotel

18. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
€307
includes taxes & fees
31 Aug - 1 Sept
West Neck Guesthouse

19. Hamlet Inn

Hamlet Inn
Southampton
United States
Shauna
€178
includes taxes & fees
8 Sept - 9 Sept
Hamlet Inn

20. Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
Hampton Bays
United States
Deborah
€127
includes taxes & fees
14 Sept - 15 Sept
Hampton Bays Hotel on Main
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Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.
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Croteaux Vineyards

10.0/10 (12 reviews)
America's only all-rosé vineyard offers a taste of Provence in New York's North Fork. Savour wine flights in the picturesque garden setting, complete with rustic barn and seaside charm.
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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)
This intimate vineyard offers personalised expert-guided wine tastings amid sustainable vineyards. Experience their unique White Merlot overlooking scenic North Fork landscapes or stay at their on-site B&B.
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Horton Point Park

9.4/10 (3 reviews)
This 1857 lighthouse stands sentinel over Long Island Sound, housing a nautical museum filled with maritime artefacts. Climb to the top for panoramic views, then follow the nature trail to the peaceful rocky beach below.
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Horton Lane Beach

9.0/10 (4 reviews)
This rocky shoreline along Long Island Sound offers peaceful views beside the historic Horton Point Lighthouse. Explore maritime heritage at the adjacent Nautical Museum, open seasonally.
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Corey Creek Winery

9.6/10 (5 reviews)
This boutique North Fork vineyard crafts innovative wines like White Cabernet Franc using indigenous yeasts. Savour sustainable vintages on their elevated deck with bay views while enjoying live music and lawn games.
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McCabe's Beach

Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
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Mattebella Vineyards

8.0/10 (4 reviews)
This family-run vineyard crafts sustainable wines in an intimate North Fork setting. Enjoy personalised tastings with garden-to-table pairings on the patio overlooking lush vines.
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Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold
A pebbled beach at sunset with the sun reflecting on the water.
Photo by Benny Goh

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Just an outstanding hotel in a breathtakingly beautiful setting!! I couldn’t be more impressed & look forward to returning! 10 stars!!"
Joan 2-night trip
Posted 1 hour ago
Water's Edge Resort & Spa
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Front desk team super nice and accommodating!"
Aldo 1-night trip
Posted 3 hours ago
Sound View Greenport
Greenview Inn Riverhead

Greenview Inn Riverhead

8/10 Good
"This recently renovated hotel had modern, well appointed rooms and was very clean. The bed and linens were comfortable but the pillows were not at all comfortable. I loved the morning breakfast area with its generous seating, many breakfast items, coffee, teas and juices."
Selwyn 1-night trip
Posted 1 day ago
Greenview Inn Riverhead
The Chequit

The Chequit

10/10 Excellent
"pretty and clean!"
Sharon 4-night trip
Posted 1 day ago
The Chequit
The Pridwin Hotel

The Pridwin Hotel

8/10 Good
"lovely place. Had an issue with my AC and there was nobody around to fix it"
Harris 2-night trip
Posted 1 day ago
The Pridwin Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

8/10 Good
"nice room for the price in season"
Frank 1-night trip
Posted 2 days ago
The Bentley Hotel Southampton
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."
mathea 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

8/10 Good
"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."
sigrid 2-night trip
Posted 5 days ago
Budget Host East End
Hyatt Place Long Island East End

Hyatt Place Long Island East End

8/10 Good
"Booked the 2nd time as our first time last year was superb. This year, we booked same type of room and requested for 1st flr room so we'll be closer to the indoor pool but ended up being assigned to a 5th floor room with view of parking lot. Other than that, location was convenient as it's next to the aquarium. Though we might reconsider staying in another hotel next year we go back to the area."
Leslie Anne 2-night trip
Posted 6 days ago
Hyatt Place Long Island East End

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
€82
27 Aug - 28 Aug
includes taxes & fees
8/10 Very good! (1,001 reviews)
Pier Blue Inn Old Saybrook - Essex
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
€113
31 Aug - 1 Sept
includes taxes & fees
7.4/10 Good! (854 reviews)
Greenview Inn Riverhead
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
€120
27 Aug - 28 Aug
includes taxes & fees
Budget Host East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
€188
16 Sept - 17 Sept
includes taxes & fees
9.6/10 Exceptional! (567 reviews)
The Bentley Hotel Southampton
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
€214
8 Sept - 9 Sept
includes taxes & fees
7.2/10 Good! (1,009 reviews)
The Atlantic Hotel
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG

1707 Old Country Rd Riverhead NY
€217
8 Sept - 9 Sept
includes taxes & fees
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Find out more about Southold

Top reasons to visit Southold

  • Stunning Beaches: Southold boasts beautiful beaches, perfect for relaxation and enjoying the scenic coastline.
  • Wine Tours: Experience exquisite winery tours and savour some of the finest wines from the region.
  • Outdoor Activities: Engage in a variety of outdoor adventures, including golfing and exploring recreational areas.
  • Rich History: Discover the intriguing Southold Historical Museum, showcasing the area's cultural heritage.
  • Charming Accommodations: Enjoy a range of delightful hotels and agritourism properties catering to diverse preferences.

Find great hotels near Southold

Explore a range of delightful hotel options in Southold, New York, perfect for a memorable getaway. From charming agritourism properties to family-friendly hotels, this area caters to diverse needs, including pet-friendly accommodations and adventure-filled experiences. Whether you seek luxurious suites or cosy rooms, Southold offers the best hotels to suit your holiday desires.

  • Sound View Greenport: Nestled along the picturesque coastline, Sound View Greenport is a charming 3.5-star hotel that offers an inviting atmosphere for beach lovers and families alike. Located 4.8km from Southold, this property features direct access to the beach, allowing guests to fully immerse themselves in the seaside experience. With a guest rating of 8.4 out of 10, it caters to both children and pets, providing complimentary cribs and window guards for added safety. The pet-friendly policy ensures that furry companions can join the holiday fun, making it an excellent choice for those travelling with pets.
  • Stirling House Bed & Breakfast: A delightful retreat located 8.0km from Southold, Stirling House Bed & Breakfast is a 3-star establishment renowned for its warm hospitality and exceptional guest rating of 9.8 out of 10. This quaint bed and breakfast offers a complimentary full breakfast, allowing guests to start their day with a hearty meal. With nearby bicycle rentals and various recreational activities, guests can easily explore the surrounding beauty. The property boasts captivating views of the waterfront, creating a serene atmosphere that is perfect for relaxation after a day of adventure.
  • Sag Harbor Inn: Situated 12.9km from Southold, Sag Harbor Inn is a sophisticated 3.5-star hotel ideal for business travellers seeking a tranquil yet convenient base. With a commendable guest rating of 9.4 out of 10, this inn combines comfort with professionalism, offering a peaceful environment for work and relaxation. The property caters to those on business trips, ensuring a seamless experience with its amenities and facilities that support productivity, while still providing a tranquil retreat in the charming village of Sag Harbor.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic escapes, making it an ideal destination for all types of travellers. Explore the charming streets of Southold, bask in the sunny weather, and enjoy family-friendly excursions in the surrounding areas. With its stunning scenery and rich historical charm, Southold promises an unforgettable experience filled with relaxation and entertainment, perfect for those seeking a memorable holiday in the heart of Long Island.

  • Greenport: Nestled a mere 6.4km from Southold, Greenport is a charming coastal city that captures the essence of seaside living. Known for its vibrant outdoor and romantic experiences, visitors flock here for its stunning beaches and recreational areas. The summer months, particularly June through August, see a surge in travellers eager to enjoy music concerts, local golf courses, and the picturesque parks. Greenport’s local landmarks, including its family-friendly beaches, offer the perfect backdrop for a relaxed day by the water, making it an ideal spot for families and couples alike.
  • Mattituck: Located 12.9km away from Southold, Mattituck is a delightful city that blends outdoor adventures with entertainment. This charming locale attracts visitors primarily during the warmer months, from June to August, when its golf courses and local markets come alive. With its proximity to beautiful beaches and tranquil lakes, Mattituck is a haven for those seeking both relaxation and recreation. The area's romantic atmosphere is enhanced by its scenic surroundings, providing a perfect escape for couples looking to unwind and enjoy nature together.
  • Hamptons: Just 16.1km from Southold lies the renowned Hamptons, a destination synonymous with beachside luxury and outdoor fun. The region experiences a seasonal influx of visitors, particularly from June to August, drawn by its stunning family beaches and picturesque lakes. Known for its romantic vibe, the Hamptons offer a plethora of activities, including golf and skiing. This area is perfect for those wanting to indulge in a blend of leisure and adventure, making it a must-visit for anyone looking to experience the quintessential summer getaway.

Things to do near Southold

Shopping

In Southold, explore local shops for unique gifts and souvenirs, such as The Village Cheese Shop and Greenport Antiques. If you're up for a drive, head to Tanger Outlets Riverhead, located 16.1km away, featuring a range of brand-name outlets and dining options.

Recreation

In Southold, the Core Wellness Spa offers a tranquil environment with a range of therapeutic treatments, including massages and facials tailored to your needs. Nearby, the Peconic Bay Winery provides a serene setting for leisurely strolls and tastings, allowing you to savour local wines amidst picturesque vineyards.

Adventure

Riverhead Raceway, located 29.0km from Southold, offers thrilling motor racing experiences with an electrifying atmosphere. Alternatively, Waterford Speedbowl, 43.5km away, provides an exciting venue for motorsport enthusiasts, showcasing competitive racing amidst a vibrant, adventurous setting.

Nightlife

In Southold, the nightlife is more laid-back, with charming venues like the Southold Fish Market offering casual dining and local drinks. For a vibrant experience, visit the nearby Greenport, known for its lively bars and waterfront views, creating a relaxed yet enjoyable atmosphere for visitors.

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

Booking tips and Expedia advantages for Southold

To save money on your trip to Southold, consider visiting between January and March when accommodation prices are lower. Tuesdays are the best days for cheaper stays, while Saturdays tend to be pricier. Use Expedia to refine your search and filter for affordable hotels. Look for package deals that combine flights and hotel bookings for added savings. Additionally, take advantage of free local activities and explore the area on foot to keep transport costs down.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday.
  • Find cheap hotels on Expedia: Utilise the search tool on Expedia to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. To uncover the most competitive prices and offers, arrange the price filter from low to high.
  • Consider bundling your trip: You can potentially save money by combining your Southold hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in and around Southold

Southold is perfect for a romantic and outdoor-themed getaway, offering a variety of attractions. Visitors can explore beautiful beaches, urban parks, and the intriguing Southold Historical Museum, while also enjoying the serene Southold Bay. This charming destination caters to those seeking cultural experiences and outdoor adventures, ensuring a delightful vacation for all types of travellers.

  • Horton Lane Beach: Experience the laid-back beach vibes at Horton Lane Beach, where you can unwind on the sandy shores and enjoy the soothing sounds of the waves. It's an ideal spot for sunbathing or a leisurely stroll along the coastline, immersing yourself in the natural beauty of Southold.
  • Orient Point County Park: Located 19.3km from Southold, this urban park offers family-friendly activities amidst scenic city surroundings. Enjoy picnicking, hiking, and exploring the great outdoors, making it a delightful retreat for those seeking a blend of nature and community.
  • Horton Point Park: Discover the rich cultural heritage at Horton Point Park, home to a historic lighthouse. Stroll through the park's scenic paths while absorbing the fascinating maritime history and enjoy panoramic views of the Long Island Sound.

Best time to go to Southold

The best time to visit Southold can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Southold falls in August, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Southold falls in January, visitor numbers are moderately low 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 SunnyModerately LowSlightly Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly 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 SunnyModerately HighSlightly High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to Southold

Accessing Southold, New York, is convenient with several major airports within reach. Newark Liberty International Airport (EWR) is situated 152.9km away, with nearby hotels such as 11 Howard and Fouquet's New York, both offering luxurious stays 14.5km from the airport. Hartford's Bradley International Airport (BDL) is located 98.2km away, with options like Candlewood Suites Windsor Locks just 1.4km from the terminal. Further, John F. Kennedy International Airport (JFK) is 123.9km distant, featuring hotels like The William Vale, a 5-star option 17.7km from the airport. Each airport provides various transportation services for easy access to Southold.

Frequently asked questions

Where is the best place to stay in Southold?
The Shoals Suites and Slips is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and private balconies. Vine & Sand is another good option for your trip. See all available top hotels, or vacation rentals in Southold.
What are some of the best holiday rentals that Southold has to offer?
The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Southold is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
What's the best dog-friendly accommodation option in Southold?
White Blossom House Inn is a top hotel for people travelling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. See more pet-friendly hotel accommodations in Southold.
What are some accommodation options with pools in Southold?
Vine & Sand: Offers buffet, a seasonal outdoor pool and free self parking. Sound View Greenport and The Atlantic Hotel are a couple of other choices that offer an on-site pool. View all hotels with pools in Southold.
What's it like to stay in Southold?
Visitors can enjoy all that Southold has to offer, including the wineries, beaches and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 142 hotels and other accommodation options to choose from. Find out more about Southold.
What should I do while I'm visiting Southold?
The picturesque setting of McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Sparkling Pointe and Mattebella Vineyards. Take a look at what more there is to see and do in Expedia's Southold guide.
What's the best way to get around Southold?
To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.
What's the weather like in Southold?
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 Southold is 1452 mm.

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