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

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Check prices for these dates

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

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Our top choices for Southold hotels

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Connor
AED 1,068
AED 1,312 total
includes taxes & fees
1 Sep - 2 Sep
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Yveline
AED 926
AED 1,373 total
includes taxes & fees
15 Sep - 16 Sep
Sound View Greenport

3. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
AED 1,962
AED 2,466 total
includes taxes & fees
13 Sep - 14 Sep
The Pridwin Hotel

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
AED 1,126
AED 1,614 total
includes taxes & fees
9 Sep - 10 Sep
Cliffside Resort Condominiums

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
AED 1,262
AED 1,442 total
includes taxes & fees
21 Sep - 22 Sep
Silver Sands Motel & Beach Bungalows

6. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
AED 1,162
AED 1,327 total
includes taxes & fees
31 Aug - 1 Sep
Shelter Island House

7. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
AED 1,128
AED 1,288 total
includes taxes & fees
20 Sep - 21 Sep
North Fork Resort

8. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
AED 1,151
AED 1,316 total
includes taxes & fees
31 Aug - 1 Sep
West Neck Guesthouse

9. The Chequit

The Chequit
The Heights
United States
Kristin
AED 1,053
AED 1,203 total
includes taxes & fees
8 Sep - 9 Sep
The Chequit

10. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
AED 902
AED 1,031 total
includes taxes & fees
14 Sep - 15 Sep
House on Chase Creek

11. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
AED 1,112
AED 1,401 total
includes taxes & fees
8 Sep - 9 Sep
Oyster Estate

12. The Menhaden

The Menhaden
Greenport
United States
Lisa
AED 1,904
AED 2,322 total
includes taxes & fees
25 Aug - 26 Aug
The Menhaden

13. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
John
AED 944
AED 1,267 total
includes taxes & fees
8 Sep - 9 Sep
The Harbor Front Inn

14. Zey Hotel

Zey Hotel
Greenport
United States
shaun
AED 744
AED 850 total
includes taxes & fees
7 Sep - 8 Sep
Zey Hotel

15. American Beech Hotel

American Beech Hotel
Greenport
United States
kerri
AED 1,450
AED 1,804 total
includes taxes & fees
7 Sep - 8 Sep
American Beech Hotel

16. Arbor View House B&B

Arbor View House B&B
East Marion
United States
Lekecia
AED 2,234
AED 2,631 total
includes taxes & fees
3 Sep - 4 Sep
Arbor View House B&B

17. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Christopher
AED 1,300
AED 1,486 total
includes taxes & fees
20 Sep - 21 Sep
Sag Harbor Inn

18. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
AED 2,479
AED 3,116 total
includes taxes & fees
15 Sep - 16 Sep
Faraway Sag Harbor

19. Head of Pond House

Head of Pond House
Water Mill
United States
Liz
AED 7,735
AED 8,838 total
includes taxes & fees
9 Sep - 10 Sep
Head of Pond House

20. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
AED 3,402
AED 3,900 total
includes taxes & fees
1 Sep - 2 Sep
Topping Rose House
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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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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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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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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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Custer Institute and Observatory

Long Island's oldest public observatory invites you to explore the cosmos through powerful telescopes every Saturday night. Enjoy guided stargazing at this historic astronomical sanctuary established in 1927.
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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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Fabulous Plumbing GEM in Southampton. We will definitely stay here again, Property is clean and it’s like having your one bedroom apartment we chose a room on the second floor, kitchen at bathroom everything great. They have fresh coffee in the lobby each morning. That was really good. Even the towels are great quality. Thumbs up all the way around. We’ll stay here again. The pictures don’t do it justice"
Sandra 3-night trip
Posted less than an hour ago
The Bentley Hotel Southampton
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Amazing stay!!!"
Maria 1-night trip
Posted 1 hour ago
The Shoals Suites and Slips
The Hampton Maid

The Hampton Maid

8/10 Good
"Nice clean and friendly hotel but the breakfast was a little pricey"
Colin 3-night trip
Posted 2 hours ago
The Hampton Maid
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

8/10 Good
"Location was great—beautifully landscaped. Employees were very helpful and personable. Our rooms were large, clean and comfortable. I would have appreciated a small microwave in the room. Meals were very good but very expensive. Alcoholic drinks and wines were delicious this year. Great bartending."
Lori 2-night trip
Posted 3 hours ago
Saybrook Point Resort & Marina
Zey Hotel

Zey Hotel

10/10 Excellent
"The balcony doesn’t have privacy Room was small and super cute, place was clean, staff is great,"
Robert 3-night trip
Posted 20 hours ago
Zey Hotel
The Chequit

The Chequit

8/10 Good
"Room small but very functional, well decorated, bath modern, and very upscale. First night the attendant was wonderful. That was on the 18th. Next day, we had a leak at the shower because the molding on shower door was not working correctly, and the floor got wet. Staff was not really very responsive to that. Had a wonderful area for eating at the restaurant with nice fire pits, very nice with an overview of the water. Nice porch to be able to sit and read in the morning or many people were doing work. One annoyance was that one of the guests was having his phone on speaker while he had a business meeting and he spoke totally out loud, and was very distracting and basically rude. He should’ve taken that conversation elsewhere and taken a walk or gone back to his room. Staff did not feel that there was any need to say anything to him. “It’s a public space” Also, there was an area right near the parking lot that was right adjacent to the building that was totally mowed in full of weeds, that really would’ve been nice if it was cleared up. In all we would return, it was very pleasant otherwise. Nice view of the harbor small but nice. And located really conveniently right by the ferry."
Maribeth 2-night trip
Posted 23 hours ago
The Chequit
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The views are amazing! The breakfast was a great perk. Short drive to town but you really don't need to leave the grounds with bar/restaurant/beach/pool all there."
Catherine 2-night trip
Posted 1 day ago
Sound View Greenport
North Fork Resort

North Fork Resort

10/10 Excellent
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."
KATHLEEN 2-night trip
Posted 2 days ago
North Fork Resort
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Great vibe and decor. Super Cozy and elegant. Best Hamptons stay! Can’t wait to come back next year."
Joseph 1-night trip
Posted 8 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
AED 348
AED 400 total
25 Aug - 26 Aug
includes taxes & fees
8/10 Very Good! (1,011 reviews)
Pier Blue Inn Old Saybrook - Essex
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
AED 389
AED 444 total
13 Sep - 14 Sep
includes taxes & fees
Greenview Inn Riverhead
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
AED 459
AED 525 total
1 Sep - 2 Sep
includes taxes & fees
Budget Host East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
AED 606
AED 784 total
7 Sep - 8 Sep
includes taxes & fees
9.6/10 Exceptional! (561 reviews)
The Bentley Hotel Southampton
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
AED 724
AED 919 total
8 Sep - 9 Sep
includes taxes & fees
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
AED 815
AED 932 total
7 Sep - 8 Sep
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Hotels in Southold with star-rating

Find out more about Southold

Top reasons to visit Southold

  • Beautiful Beaches: Southold features stunning beaches perfect for relaxation and recreation.
  • Wine Tastings: Experience the renowned vineyards of the region through delightful wine tastings.
  • Outdoor Adventures: Enjoy a variety of outdoor activities, from scenic hikes to water sports.
  • Charming Neighborhoods: Explore picturesque neighborhoods filled with local culture and history.
  • Diverse Accommodations: Choose from cozy hotels to unique agritourism stays that suit all preferences.

Find great hotels near Southold

Southold offers a diverse selection of accommodations, from charming agritourism properties to cozy hotels perfect for families and adventure seekers. With pet-friendly options and proximity to beautiful beaches, you'll find the ideal spot for your vacation. Explore the various hotels in Southold, read reviews, and discover the perfect place to unwind and enjoy the stunning North Fork experience.

  • Sound View Greenport: Nestled just 4.8km from Southold, Sound View Greenport is a charming 3.5-star hotel perfect for families, business travelers, and beach enthusiasts alike. With direct access to the beach, guests can indulge in sun-soaked relaxation and seaside adventures. The hotel goes the extra mile to accommodate families with amenities like free cribs and window guards for children, ensuring a safe and enjoyable stay. Visitors can expect a welcoming atmosphere that caters to both leisure and work needs, making it an ideal getaway for all.
  • The Harbor Front Inn: Located 6.4km from Southold, The Harbor Front Inn is a delightful 3.5-star accommodation that welcomes both business travelers and pet owners. This pet-friendly property permits dogs in designated areas, ensuring that your furry friends can join in on the vacation fun. The inn features a warm, inviting ambiance, making it a perfect spot for those looking to blend work with relaxation. Guests appreciate the thoughtful amenities and the friendly service that enhance their overall experience, making it a popular choice for a memorable stay.
  • Sag Harbor Inn: Positioned 12.9km from Southold, the Sag Harbor Inn offers a sophisticated 3.5-star experience tailored for business travelers. The inn provides a tranquil retreat with comfortable accommodations and essential amenities for professionals on the go. Its strategic location allows for easy access to local attractions and dining, making it a convenient choice for those looking to explore the area while maintaining their work commitments. Guests can enjoy a peaceful atmosphere that seamlessly blends comfort and functionality.

Where to stay near Southold

Southold, located on Long Island's beautiful North Fork, offers a perfect blend of romantic outdoor adventures and family-friendly activities. Enjoy scenic excursions, explore charming neighborhoods, and indulge in luxury experiences. With its sunny weather and rich historical backdrop, Southold is an ideal destination for relaxation and entertainment. Discover nearby attractions that enhance your vacation, making it a memorable getaway in New York State.

  • Hamptons: Situated 16.1km from Southold, the Hamptons are renowned for their beautiful beaches and upscale atmosphere. This area attracts visitors seeking outdoor adventures and romantic getaways, especially during peak season from June to August. Outdoor enthusiasts can enjoy a variety of activities, including golfing and attending music concerts. Local landmarks like scenic beaches and picturesque lakes make the Hamptons a prime destination for leisure and relaxation.
  • Greenport: Greenport is a charming city located 6.4km from Southold, perfect for travelers looking for a blend of outdoor experiences and romantic settings. With a moderately seasonal influx of visitors peaking in the summer months, Greenport offers plenty of recreational activities including golf and music events. Its proximity to beautiful parks and family-friendly beaches makes it an ideal spot for families and couples alike, ensuring a delightful experience for all.
  • Sag Harbor: Only 12.9km away from Southold, Sag Harbor is a picturesque city that boasts a rich maritime history and vibrant cultural scene. Visitors flock here for its spectacular beaches and outdoor experiences, particularly in the summer months. With access to golf courses, ski fields, and local attractions like lighthouses and family beaches, Sag Harbor provides an excellent range of activities for all types of travelers, making it a must-visit destination.

Things to do near Southold

Southold offers a delightful mix of romantic and outdoor activities perfect for a vacation. Visitors can enjoy skiing at local resorts, as well as take part in popular wine tastings that showcase the region's renowned vineyards. With its scenic landscapes and entertainment options, Southold is an ideal destination for those seeking adventure and relaxation alike.

Shopping

In Southold, visit the Greenport Farmers' Market, just 6.4km away, for local produce and handmade goods. The Style Bar and Love Lane, both 12.9km away, offer a unique shopping experience with family-friendly vibes. If you're up for a drive, check out nearby malls for more options.

Recreation

Goldsmith's Inlet Park offers a tranquil retreat with scenic views and calming vibes, perfect for relaxation. Noyac Golf Club provides a vibrant outdoor atmosphere for golf enthusiasts, while Shelter Island Whale's Tail mini-golf promises family fun and adventure in a lively setting.

Adventure

Splish Splash Water Park is an exhilarating waterpark 30.6km from Southold, offering thrilling slides and family-friendly attractions for a splashing good time. For motor racing enthusiasts, Riverhead Raceway, 29.0km away, provides an adrenaline-pumping experience with exciting races. Enjoy the scenic views on the Walking Dunes Trailhead, located 33.8km from Southold, perfect for hiking and outdoor adventures.

Nightlife

Experience the charm of Southold's nightlife with a visit to the Greenport Carousel for a whimsical family outing. For a more romantic evening, catch a show at Bay Street Theatre or Guild Hall, both offering a blend of entertainment and culture just a short drive away.

*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 for lower accommodation rates. Tuesdays are typically the cheapest days to stay, while Saturdays are the priciest. Use Expedia to compare hotel prices and find exclusive discounts, and don’t forget to explore eco-certified options for sustainable stays. You can maximize savings by booking a package that combines flights, hotels, and activities. Additionally, look for free activities in the area to enhance your experience without overspending.

  • 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: Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can arrange the results to display prices from lowest to highest, making it easy to find the most affordable hotels right away. Additionally, you have the option to refine your search by hotel type; for instance, by selecting the Eco-certified filter, you'll discover sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Southold hotel reservation with your flights and activities when you book an Expedia package.

Find the best attractions near Southold

Southold is perfect for a romantic getaway or an outdoor adventure, boasting beautiful beaches, urban parks, and fascinating history museums. Visitors can immerse themselves in the local culture while enjoying a variety of outdoor experiences. Whether you're looking to relax by the beach or explore the area's rich history, Southold offers a delightful mix of attractions that cater to all types of travelers.

  • 67 Steps Beach: Enjoy the serene beach vibes at 67 Steps Beach, located 8.0km from Southold. This charming beach offers a unique experience with its picturesque steps leading down to the sandy shores, perfect for sunbathing, swimming, or simply relaxing by the waves.
  • Railroad Museum of Long Island: Immerse yourself in local culture at the Railroad Museum of Long Island, just 6.4km away. Discover the rich history of railroads in the region through fascinating exhibits, vintage trains, and interactive displays that appeal to all ages.
  • Sag Harbor Marine Park: Adventure awaits at Sag Harbor Marine Park, located 12.9km from Southold. This marina offers thrilling outdoor activities, including kayaking, fishing, and beachcombing, all while surrounded by stunning natural beauty.

Best time to go to Southold

The best time to visit Southold is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

When planning your vacation to Southold, New York, you'll find several major airports nearby. Islip, NY (ISP-MacArthur) is 64.4km away, with good hotel options like the 3.5-star Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 6.4km from the airport. New Haven, CT (HVN-Tweed - New Haven Regional) is 45.1km from Southold, featuring the 4-star Omni New Haven Hotel at Yale and The Blake Hotel, both 4.8km away. East Hampton, NY (HTO) is the closest, located 19.3km away, with luxurious options like the 5-star Mill House Inn and the 4.5-star Topping Rose House, each just a short drive from the airport.

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. Vine & Sand is another good option for your visit. See all available top hotels, or vacation rentals in Southold.
What's the top vacation rental in Southold?
The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental outside of Southold is equipped with a barbecue grill, 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, 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?
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 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 142 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 Mattebella 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.