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

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Our top choices for Southold hotels

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
¥31,871
¥40,362 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
¥27,551
¥35,987 total
includes taxes & fees
Nov 3 - Nov 4
Sound View Greenport

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
¥45,145
¥51,579 total
includes taxes & fees
Oct 13 - Oct 14
Silver Sands Motel & Beach Bungalows

4. The Menhaden

The Menhaden
Greenport
United States
Lisa
¥54,559
¥68,650 total
includes taxes & fees
Nov 4 - Nov 5
The Menhaden

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Joseph
¥23,149
¥30,958 total
includes taxes & fees
Nov 3 - Nov 4
The Harbor Front Inn

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
¥26,681
¥47,996 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums

7. Zey Hotel

Zey Hotel
Greenport
United States
Renee
¥26,637
¥30,432 total
includes taxes & fees
Oct 7 - Oct 8
Zey Hotel

8. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
¥31,767
¥36,293 total
includes taxes & fees
Oct 15 - Oct 16
Shelter Island House

9. North Fork Resort

North Fork Resort
Greenport
United States
Harold
¥39,249
¥44,843 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort

10. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
¥39,589
¥51,543 total
includes taxes & fees
Oct 7 - Oct 8
American Beech Hotel

11. The Chequit

The Chequit
The Heights
United States
Patrick
¥20,740
¥23,696 total
includes taxes & fees
Nov 4 - Nov 5
The Chequit

12. Oyster Estate

Oyster Estate
Greenport
United States
Allison
¥38,531
¥48,545 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate

13. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
¥34,569
¥39,494 total
includes taxes & fees
Nov 3 - Nov 4
Sag Harbor Inn

14. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
¥29,191
¥33,350 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek

15. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
¥64,664
¥81,268 total
includes taxes & fees
Nov 2 - Nov 3
Faraway Sag Harbor

16. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Rich
¥22,573
¥25,790 total
includes taxes & fees
Oct 21 - Oct 22
The Bentley Hotel Southampton

17. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
¥92,811
¥106,589 total
includes taxes & fees
Oct 19 - Oct 20
Topping Rose House

18. Shorewood Inn

Shorewood Inn
Riverhead
United States
Heather
¥13,496
¥15,419 total
includes taxes & fees
Oct 11 - Oct 12
Shorewood Inn

19. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Jon
¥46,739
¥53,399 total
includes taxes & fees
Oct 14 - Oct 15
A Room At The Beach

20. Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG
Riverhead
United States
LUIS
¥16,259
¥18,577 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Express & Suites Riverhead - Long Island by IHG
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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. Savor 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. Savor 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 personalized 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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Osprey's Dominion

9.6/10 (5 reviews)
This award-winning North Fork winery showcases sustainable viticulture through distinctive Sauvignon Blanc and Merlot offerings. Enjoy tastings on their spacious lawn with weekend live music and picnic areas.
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The Old Field Vineyards

9.6/10 (5 reviews)
This family-owned vineyard, Long Island's oldest continuously operated winery, offers handcrafted wines in a rustic setting. Enjoy tastings on expansive lawns overlooking Southold Bay.
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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 personalized tastings with garden-to-table pairings on the patio overlooking lush vines.
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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 artifacts. 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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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 coastal landscape with a sunset, a marina, and a residential area.

Top Southold Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"excellent stay...staff was friendly. will stay here again."
Joshua 1-night trip
Posted less than an hour ago
The Hampton Maid
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"The rooms have recently been renovated and are very well designed."
Frank 1-night trip
Posted 3 hours ago
The Bentley Hotel Southampton
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"A really nice jewel in this CT coast. I found it thanks to Expedia and it didn’t disappoint. Super large king room. The property is gorgeous. Gardens and decks provide best views of the sound. A great spot for sunset"
Roger 1-night trip
Posted 5 hours ago
Water's Edge Resort & Spa
The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
Antrii 1-night trip
Posted 12 hours ago
The Harbor Front Inn
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"This place was great! The restaurant was delicious, the lounge was great, the room was amazing and to top it off the view from our hotel was incredible. The staff were so generous and accommodating. We went for a long weekend/anniversary celebration. I wish we stayed longer and took advantage of the rest of the amenities the hotel has to offer. We will definitely go back."
Ryan 2-night trip
Posted 17 hours ago
Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 1 day ago
The Atlantic Hotel
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great stay. The hotel was clean and convenient. Highly recommend."
Bryan 1-night trip
Posted 2 days ago
Hilton Garden Inn Riverhead
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Friendly staff. Convenient location."
Rodhmir 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."
Richard 1-night trip
Posted 3 days ago
Hampton Bays Hotel on Main

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
¥12,879
¥14,811 total
Oct 12 - Oct 13
includes taxes & fees
8/10 Very Good! (1,006 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
¥14,049
¥16,052 total
Oct 11 - Oct 12
includes taxes & fees
6.8/10 (894 reviews)
Budget Host East End
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
¥16,340
¥18,668 total
Nov 3 - Nov 4
includes taxes & fees
7.4/10 Good! (883 reviews)
Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
¥14,088
¥20,042 total
Oct 28 - Oct 29
includes taxes & fees
7.2/10 Good! (1,005 reviews)
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
¥22,573
¥25,790 total
Oct 21 - Oct 22
includes taxes & fees
9.6/10 Exceptional! (595 reviews)
The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
¥33,385
¥38,141 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (799 reviews)
The Hampton Maid

Find out more about Southold

Top reasons to visit Southold

  • Charming Beaches: Southold boasts beautiful beaches where visitors can relax, swim, and enjoy stunning sunsets.
  • Winery Tours: Experience local flavors by touring the nearby wineries, sampling exquisite wines in a picturesque setting.
  • Rich History: Discover local heritage at the Southold Historical Museum, showcasing the town's fascinating past.
  • Outdoor Activities: Enjoy golfing and exploring recreational areas, perfect for outdoor enthusiasts and nature lovers.
  • Cozy Accommodations: Stay in delightful agritourism properties and charming bed & breakfasts, catering to all traveler preferences.

Find great hotels near Southold

Explore the charming accommodations in Southold, New York, where you can find a variety of lodging options, including delightful agritourism properties and cozy bed & breakfasts. Whether you're seeking adventure, a pet-friendly environment, or a family-friendly experience, Southold's hotels cater to every traveler's needs. With a selection of hotel rooms and suites available, you're sure to find the perfect stay for your vacation.

  • Sound View Greenport: Nestled just 5km from Southold, Sound View Greenport is a charming 3.5-star hotel offering a delightful beach experience. Rated 8.4 out of 10 by guests, this property is ideal for families and business travelers alike. With direct access to the beach, you can enjoy sun-soaked days by the water. The hotel is particularly family-friendly, featuring amenities such as free cribs and window guards for children, ensuring a safe and comfortable stay for your little ones.
  • Sag Harbor Inn: Located 13km from Southold, the Sag Harbor Inn is a stylish 3.5-star lodging with an impressive guest rating of 9.4 out of 10. This hotel caters primarily to business travelers, providing a serene environment for work and relaxation. With its convenient location, guests can easily access local businesses and attractions, making it a practical choice for those on the go. The inn’s pleasant atmosphere and attentive service set the stage for a productive stay.
  • The Harbor Front Inn: Situated 6km from Southold, The Harbor Front Inn is a welcoming 3.5-star hotel with a guest rating of 8.8 out of 10. This property is pet-friendly, accommodating travelers who wish to bring their furry companions along. With a variety of pet amenities, including a waived fee for service animals and specific policies for dogs, this inn ensures a comfortable stay for both you and your pet. The Harbor Front Inn also caters to business travelers, combining convenience with a relaxed atmosphere.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic escapes, perfect for any traveler. Explore its charming neighborhoods, soak up the sunny weather, and enjoy family-friendly excursions. Nearby attractions showcase stunning scenery and rich historical experiences. Whether you're looking for luxury or a quaint atmosphere, Southold embodies the charm of coastal living, making it an ideal destination for an unforgettable vacation.

  • Hamptons: Located 16km away from Southold, the Hamptons are synonymous with luxury and relaxation. This charming destination attracts visitors seeking a mix of beautiful beaches, outdoor activities, and romantic getaways. The area sees a seasonal influx of travelers, especially during the summer months from June to August, when the beaches come alive with sunbathers and water sports enthusiasts. Notable attractions include stunning family-friendly beaches, picturesque lakes, and golf courses that cater to both beginners and seasoned players. Whether you're looking to unwind by the shore or enjoy an active day outdoors, the Hamptons offer a delightful blend of experiences.
  • Greenport: Just 6km from Southold, Greenport is a picturesque village that embodies the charm of the North Fork. Known for its vibrant arts scene and waterfront views, this city welcomes a variety of travelers, particularly during the peak season from June to August. Visitors flock to Greenport for its outdoor adventures, romantic ambiance, and stunning beaches. Spend your day exploring local parks, enjoying music concerts, or indulging in fresh seafood at quaint restaurants. With its friendly atmosphere and scenic beauty, Greenport is perfect for couples and families alike looking to create lasting memories.
  • Sag Harbor: Approximately 13km from Southold, Sag Harbor is a historic whaling village that offers a unique blend of culture and natural beauty. This lively city attracts visitors year-round, peaking in the summer months. Travelers are drawn to Sag Harbor for its outdoor recreation, stunning beaches, and romantic settings. Enjoy activities such as golfing or skiing, and take advantage of the beautiful family-friendly beaches and serene lakes. With its charming shops, art galleries, and rich maritime history, Sag Harbor provides an enchanting experience for all types of visitors.

Things to do near Southold

Shopping

In Southold, explore local shops for unique gifts and souvenirs. If you're up for a drive, visit Tanger Outlets in Riverhead, about 18km away, featuring a variety of brand-name stores and a vibrant shopping atmosphere.

Recreation

In Southold, indulge in rejuvenating treatments at the Spa at East Wind, surrounded by lush gardens. For a serene escape, visit the North Fork Wellness Center, which offers yoga classes and holistic therapies to enhance your mind and body connection.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 29km from Southold, where you can feel the adrenaline rush of fast cars and lively competition. Alternatively, head to Waterford Speedbowl, 43km away, for more exciting races in a vibrant atmosphere filled with sports energy.

Nightlife

In Southold, you can unwind at local wineries like Sparkling Pointe, where you can enjoy wine tastings in a relaxing atmosphere. For a more lively experience, explore nearby Greenport, which boasts charming bars and live music venues, perfect for a fun night out with friends.

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

Find the best attractions in and around Southold

Southold offers a delightful blend of outdoor and romantic activities, perfect for an entertaining vacation. Visitors can explore the scenic Southold Bay and delve into local history at the Southold Historical Museum. The area also features beautiful beaches and urban parks, catering to those seeking cultural experiences and outdoor adventures. Whether you're relaxing by the shore or enjoying the charming local attractions, Southold promises a memorable getaway.

  • The Hamptons Beaches: Located 19km from Southold, The Hamptons Beaches offer an idyllic seaside experience with pristine sands and vibrant beach vibes. Enjoy sunbathing, swimming, and beachside dining while soaking in the picturesque coastal scenery.
  • Orient Point County Park: Also 19km from Southold, Orient Point County Park is an urban park ideal for family outings. With outdoor activities such as hiking and picnicking, visitors can relish the natural beauty of the area while enjoying a peaceful escape from city life.
  • Horton Point Park: Situated within Southold, Horton Point Park features a historic lighthouse that reflects the area's rich maritime culture. Explore scenic trails and enjoy breathtaking views of the Long Island Sound, immersing yourself in the local heritage.

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

Traveling to Southold, New York, is convenient with several major airports nearby. New York, NY (JFK-John F. Kennedy Intl.) is 124km away, with excellent hotels like The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty Intl. Airport (EWR) is 153km away, with luxurious options like The Dominick and Four Seasons Hotel New York Downtown, both 14km from the airport. Lastly, LaGuardia Airport (LGA) is 126km from Southold, featuring upscale hotels such as Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, both within 10km of the airport. These hotels offer easy access to their respective airports for a smooth travel experience.

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 traveler data. This hotel offers a restaurant and private balconies. Other good choices for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Water's Edge Resort & Spa. See all available top hotels, or vacation rentals in Southold.
What's the top vacation rental in Southold?
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental outside of Southold offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, the majority of room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
Where can I learn more about changing or cancelling my trip to Southold?
To access more information about rescheduling or cancelling your trip to Southold, head over to our customer service page.
What's the best pet-friendly accommodation in Southold?
White Blossom House Inn is a top hotel for people traveling 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.
Where is the best hotel to stay near Sparkling Pointe?
White Blossom House Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and private patios. It's located just a short 0.9 mi (1.4 km) from Sparkling Pointe.
What about the best place to stay close to Mattebella Vineyards?
One of the top choices for your stay is White Blossom House Inn, located a short 0.7 mi (1.1 km) from Mattebella Vineyards, and this hotel offers free parking and private patios.
What are some accommodations with pools in Southold?
Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport and The Atlantic Hotel are a couple of other choices that feature an onsite pool. View all hotels with pools in Southold.
What's the best place to stay near John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
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 141 hotels and other accommodations to choose from. Find out more about Southold.
What should I see while I'm in 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 agenda are Sparkling Pointe and Croteaux Vineyards. Check out what more to see and do in Expedia's Southold guide.
How should I 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.

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