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

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Sep 24 - Sep 25
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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
¥31,942
¥40,450 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
¥36,550
¥46,292 total
includes taxes & fees
Oct 25 - Oct 26
Sound View Greenport

3. Zey Hotel

Zey Hotel
Greenport
United States
Renee
¥26,708
¥30,515 total
includes taxes & fees
Sep 27 - Sep 28
Zey Hotel

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Jordan
¥33,441
¥42,740 total
includes taxes & fees
Oct 25 - Oct 26
The Harbor Front Inn

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
¥44,887
¥51,284 total
includes taxes & fees
Oct 26 - Oct 27
Silver Sands Motel & Beach Bungalows

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
¥43,861
¥67,725 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums

7. The Chequit

The Chequit
The Heights
United States
Kristin
¥30,889
¥35,292 total
includes taxes & fees
Oct 26 - Oct 27
The Chequit

8. The Menhaden

The Menhaden
Greenport
United States
Lisa
¥52,786
¥66,638 total
includes taxes & fees
Sep 29 - Sep 30
The Menhaden

9. North Fork Resort

North Fork Resort
Greenport
United States
Harold
¥40,886
¥46,711 total
includes taxes & fees
Oct 25 - Oct 26
North Fork Resort

10. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
¥36,354
¥47,886 total
includes taxes & fees
Oct 1 - Oct 2
American Beech Hotel

11. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
¥31,852
¥36,390 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House

12. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
¥34,072
¥38,928 total
includes taxes & fees
Oct 8 - Oct 9
House on Chase Creek

13. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Renee
¥16,951
¥19,494 total
includes taxes & fees
Sep 30 - Oct 1
Quality Inn Old Saybrook - Westbrook

14. Clinton Motel

Clinton Motel
Clinton
United States
Selena
¥12,503
¥14,378 total
includes taxes & fees
Sep 27 - Sep 28
Clinton Motel

15. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
¥51,279
¥58,588 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn

16. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
¥50,014
¥63,013 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate

17. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
¥49,618
¥56,690 total
includes taxes & fees
Oct 1 - Oct 2
West Neck Guesthouse

18. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
United States
Stacy
¥17,414
¥20,026 total
includes taxes & fees
Oct 4 - Oct 5
Spark by Hilton Guilford

19. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Russell
¥12,913
¥14,850 total
includes taxes & fees
Sep 29 - Sep 30
Pier Blue Inn Old Saybrook - Essex

20. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
Old Saybrook
United States
Carmen
¥12,503
¥14,811 total
includes taxes & fees
Sep 27 - Sep 28
Motel 6 Old Saybrook, CT
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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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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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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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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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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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Corey Creek Winery

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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"The person checking us in was very pleasant and helpful. The rooms were clean and well kept, noise level was low and not disturbing. Price was very reasonable."
Steven 1-night trip
Posted 4 hours ago
Pier Blue Inn Old Saybrook - Essex
Zey Hotel

Zey Hotel

10/10 Excellent
"Lovely hotel, great location and lovely courtyard!"
Martina 1-night trip
Posted 1 day ago
Zey Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."
Linda 3-night trip
Posted 1 day ago
Water's Edge Resort & Spa
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"
Susan 1-night trip
Posted 2 days ago
The Shoals Suites and Slips
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Beautiful and clean room and property with a gorgeous marina view. Friendly and helpful staff. I thoroughly enjoyed my stay, and intend to return."
Joseph 1-night trip
Posted 2 days ago
Saybrook Point Resort & Marina
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 3 days ago
Budget Host East End
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great place."
Christine 3-night trip
Posted 5 days ago
Hilton Garden Inn Riverhead
Hyatt Place Long Island East End

Hyatt Place Long Island East End

8/10 Good
"Great hotel, Not for $500 per night though"
Brian 2-night trip
Posted 5 days ago
Hyatt Place Long Island East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"I really appreciate the hotel. I will came back"
Elaine 1-night trip
Posted 5 days ago
The Bentley Hotel Southampton

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
¥12,913
¥14,850 total
Sep 29 - Sep 30
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
¥14,086
¥16,094 total
Sep 27 - Sep 28
includes taxes & fees
6.8/10 (893 reviews)
Budget Host East End
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
¥18,666
¥21,326 total
Sep 28 - Sep 29
includes taxes & fees
Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
¥15,359
¥21,517 total
Oct 25 - Oct 26
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
¥25,089
¥32,622 total
Oct 5 - Oct 6
includes taxes & fees
9.6/10 Exceptional! (589 reviews)
The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
¥33,474
¥38,245 total
Oct 13 - Oct 14
includes taxes & fees
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: Provides a seasonal outdoor pool, an indoor pool, and a private beach. The Atlantic Hotel and Sound View Greenport 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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