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

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Sep 11 - Sep 12
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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
₩272,434
₩345,001 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

2. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
₩136,537
₩157,017 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook

3. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
United States
Stacy
₩157,730
₩181,390 total
includes taxes & fees
Oct 6 - Oct 7
Spark by Hilton Guilford

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Michael
₩351,096
₩439,687 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn

5. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
₩110,134
₩126,656 total
includes taxes & fees
Sep 16 - Sep 17
Pier Blue Inn Old Saybrook - Essex

6. Clinton Motel

Clinton Motel
Clinton
United States
Selena
₩105,288
₩121,081 total
includes taxes & fees
Sep 14 - Sep 15
Clinton Motel

7. Zey Hotel

Zey Hotel
Greenport
United States
Renee
₩227,787
₩260,247 total
includes taxes & fees
Sep 15 - Sep 16
Zey Hotel

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
₩372,896
₩426,040 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows

9. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
₩93,140
₩107,111 total
includes taxes & fees
Sep 21 - Sep 22
Lamplighter Motel - Clinton, Connecticut

10. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
₩437,351
₩499,674 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn

11. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
DONNA
₩241,961
₩301,543 total
includes taxes & fees
Oct 7 - Oct 8
Water's Edge Resort & Spa

12. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
₩684,317
₩860,016 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel

13. Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End
Riverhead
United States
Nataliya
₩235,684
₩269,268 total
includes taxes & fees
Oct 5 - Oct 6
Residence Inn by Marriott New York Long Island East End

14. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Veronica
₩263,221
₩300,730 total
includes taxes & fees
Oct 12 - Oct 13
Hyatt Place Long Island East End

15. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
₩464,349
₩585,054 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate

16. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
₩290,596
₩332,009 total
includes taxes & fees
Oct 6 - Oct 7
House on Chase Creek

17. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
₩387,153
₩561,782 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums

18. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
₩358,587
₩448,237 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport

19. The Captain Stannard

The Captain Stannard
Westbrook Center
United States
Deborah
₩315,756
₩350,489 total
includes taxes & fees
Sep 14 - Sep 15
The Captain Stannard

20. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
₩201,975
₩264,503 total
includes taxes & fees
Sep 28 - Sep 29
The Bentley Hotel Southampton
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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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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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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

8/10 Good
"Deverian actualizar las tv’s"
Maria 1-night trip
Posted less than an hour ago
Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"
Nancy 2-night trip
Posted 1 hour ago
The Atlantic Hotel
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Not the usual Marriott standards, but a decent cheap room"
Jo-Ann 1-night trip
Posted 3 hours ago
Quality Inn Old Saybrook - Westbrook
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Central to go any place within Long Island"
Eneida 4-night trip
Posted 3 hours ago
Hyatt Place Long Island East End
Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Renovated rooms Plenty of hot water with good pressure Immaculate Need a clean room and comfortable bed at a very reasonable price stay here"
carmen 1-night trip
Posted 7 hours ago
Greenview Inn Riverhead
North Fork Resort

North Fork Resort

10/10 Excellent
"This property is so awesome! Adorable cottages, not very big, but sufficient. We were 2 couples, and we managed. Very quaint an comfortable. Services were provided if asked. They give you everything you need. I may buy in or for sure go back as a guest next year. We loved it, and it's so convenient to town, restaurants, and wineries all around you."
LISA 2-night trip
Posted 2 days ago
North Fork Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"Such an amazing hotel to stay for the weekend"
Olivia 1-night trip
Posted 3 days ago
Zey Hotel
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 9 days ago
Faraway Sag Harbor

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
₩110,134
₩126,656 total
Sep 16 - Sep 17
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
₩119,260
₩136,254 total
Sep 13 - Sep 14
includes taxes & fees
Budget Host East End
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT
₩136,537
₩157,017 total
Oct 4 - Oct 5
includes taxes & fees
7.8/10 Good! (1,005 reviews)
Quality Inn Old Saybrook - Westbrook
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
₩159,795
₩216,065 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,004 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
₩225,425
₩257,549 total
Oct 12 - Oct 13
includes taxes & fees
Holiday Inn Express & Suites Riverhead - Long Island by IHG
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
₩349,740
₩399,576 total
Sep 14 - Sep 15
includes taxes & fees
The Hampton Maid

Find out more about Southold

Top reasons to visit Southold

  • Stunning Beaches: Southold boasts beautiful beaches perfect for relaxing and enjoying picturesque sunsets.
  • Vineyard Tours: Experience local culture through delightful vineyard tours, sampling exquisite wines.
  • Outdoor Activities: Enjoy a range of outdoor adventures, including golf and recreational areas.
  • Rich History: Explore the Southold Historical Museum and nearby towns for a glimpse into the area's past.
  • Charming Accommodations: Choose from diverse lodging options, including pet-friendly and family-oriented stays.

Find great hotels near Southold

Discover the charm of Southold, New York, where a variety of hotel accommodations await you. Whether you're seeking adventure, a pet-friendly stay, or a family vacation experience, Southold offers an array of options, including agritourism properties and hotels designed for every type of traveler. Explore the best Southold hotels to find the perfect room or suite that suits your needs and enhances your getaway.

  • Sound View Greenport: Located only 5km from Southold, Sound View Greenport is a charming 3.5-star hotel offering a delightful beach experience. With a guest rating of 8.4 out of 10, this property is ideal for families and business travelers alike. The hotel features direct beach access, allowing guests to soak up the sun and enjoy ocean activities right at their doorstep. Families will appreciate the thoughtful amenities for children, including free cribs and Window Guards for safety. Combining a picturesque setting with convenient amenities, Sound View Greenport is a great choice for those seeking a relaxed getaway.
  • Sag Harbor Inn: Situated 13km from Southold, Sag Harbor Inn boasts a stellar 9.4 out of 10 guest rating, making it a prime choice for business travelers. This 3.5-star property offers a sophisticated atmosphere with a focus on comfort and convenience. Guests can expect well-appointed rooms that cater to a professional environment, perfect for those traveling for work. The inn's location puts you near the charming village of Sag Harbor, providing easy access to local dining and shopping options. Sag Harbor Inn blends classic hospitality with modern amenities for a refined stay.
  • The Harbor Front Inn: Just 6km from Southold, The Harbor Front Inn stands out with its blend of business-friendly accommodations and pet-friendly policies, earning a solid guest rating of 8.8 out of 10. This 3.5-star hotel allows pets with specific policies, making it an excellent choice for travelers who want to bring their furry friends along. The property offers comfortable rooms with beautiful views, as well as convenient access to local attractions. With its welcoming atmosphere and accommodating services, The Harbor Front Inn provides a unique experience for both business and leisure travelers.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic getaways. With its charming scenery and family-friendly atmosphere, visitors can enjoy sunny weather while exploring local vineyards and beautiful beaches. Nearby towns add historical richness and luxury experiences, making it a perfect base for excursions. Discover the unique charm of Southold as you immerse yourself in its vibrant community and stunning landscapes, ensuring an unforgettable vacation experience.

  • Hamptons: Located 16km from Southold, the Hamptons are famous for their stunning beaches and vibrant outdoor scene. This upscale destination attracts a seasonal influx of visitors, peaking from June to August. Ideal for couples seeking a romantic getaway, the Hamptons offer a variety of activities, including golf courses and ski fields for those who enjoy outdoor adventures. Local landmarks such as the beautiful beaches and serene lakes provide picturesque spots perfect for relaxation and family fun.
  • Greenport: Just 6km from Southold, Greenport is a charming village known for its rich maritime history and laid-back atmosphere. With a similar seasonal visitor pattern, Greenport’s peak season runs from June to August. Travelers flock here for romantic strolls along the waterfront, outdoor activities, and vibrant local events, including music concerts. The town features lovely parks and beautiful family-friendly beaches, making it a great spot for both relaxation and recreation.
  • Sag Harbor: Located 13km from Southold, Sag Harbor combines historic charm with a modern flair, attracting visitors seeking beachside tranquility and outdoor fun. The peak travel season mirrors its neighbors, bustling from June to August. Sag Harbor is perfect for a romantic escape, with numerous golf courses and beautiful lakes nearby for leisurely days. The picturesque beaches and family-friendly areas make it an ideal destination for those looking to soak up the sun and enjoy the scenic beauty of the region.

Things to do near Southold

Shopping

In Southold, you can explore charming local shops like the Southold General Store for unique gifts and souvenirs. If you're up for a drive, visit the Tanger Outlets in Riverhead for a variety of brand-name stores and discounts.

Recreation

Explore the tranquility of the Southold Wellness Center, where you can indulge in spa treatments and yoga classes designed to rejuvenate your spirit. Afterward, take a leisurely stroll along the beautiful beaches for fresh air and scenic views, perfect for unwinding and connecting with nature.

Adventure

At Riverhead Raceway, located 29km from Southold, you can experience thrilling motor racing events in a vibrant atmosphere filled with adrenaline. Waterford Speedbowl, 43km away, offers an exciting motorsport experience, showcasing various racing formats that cater to adventure seekers and sports enthusiasts alike.

Nightlife

Experience the cozy atmosphere at the Southold Fish Market, where you can enjoy fresh seafood and a casual vibe. For a lively night, visit the Greenport Harbor Brewing Co. to sample local craft beers while mingling with fellow visitors and enjoying occasional live music.

*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, New York, is perfect for outdoor and romantic getaways, offering attractions like beautiful beaches, urban parks, and the Southold Historical Museum. Visitors can enjoy the scenic Southold Bay, immerse themselves in local culture, and partake in various outdoor activities. Whether you're looking to relax by the shore or explore the area's rich history, Southold has something for everyone seeking a memorable vacation experience.

  • Horton Lane Beach: Enjoy the laid-back beach vibes at Horton Lane Beach, a serene spot within Southold. This charming beach offers a tranquil escape where you can relax, sunbathe, or take a leisurely stroll along the shore.
  • Orient Point County Park: Located 19km from Southold, this urban park is ideal for family outings and outdoor activities. With scenic views and ample space for picnicking, hiking, and exploring nature, it’s a great place to unwind and enjoy the fresh air.
  • Shinnecock Nation Cultural Center and Museum: Situated 19km away, this museum offers a deep dive into the rich culture and history of the Shinnecock Nation. Engage with exhibits that celebrate their heritage and traditions, providing a unique educational experience.

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's JFK Airport is approximately 124km away, with luxury hotels like The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty International Airport (EWR), located 153km from Southold, offers upscale accommodations such as The Dominick and Four Seasons Hotel New York Downtown, both 14km away. LaGuardia Airport (LGA) is about 126km from Southold, with notable hotels like Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, situated 5 to 10km from the airport. These airports provide ample options for travelers visiting 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 traveler data. This hotel offers a restaurant and private balconies. Other good choices for your trip to the area are Sound View Greenport and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or 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?
Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. The Atlantic Hotel and Water's Edge Resort & Spa 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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