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

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15 Aug - 16 Aug
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16 Aug - 17 Aug
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21 Aug - 23 Aug
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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
Rp5.198.453
Rp6.386.159 total
includes taxes & fees
1 Sept - 2 Sept
The Shoals Suites and Slips

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
David
Rp4.938.521
Rp6.561.315 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
Rp8.735.230
Rp9.980.089 total
includes taxes & fees
14 Sept - 15 Sept
Silver Sands Motel & Beach Bungalows

4. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
Rp5.637.789
Rp6.441.252 total
includes taxes & fees
25 Aug - 26 Aug
Shelter Island House

5. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
Rp5.818.963
Rp7.331.603 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
Rp5.463.797
Rp7.831.758 total
includes taxes & fees
14 Sept - 15 Sept
Cliffside Resort Condominiums

7. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
United States
Stacy
Rp1.890.988
Rp2.174.639 total
includes taxes & fees
13 Sept - 14 Sept
Spark by Hilton Guilford

8. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
John
Rp1.803.201
Rp2.073.681 total
includes taxes & fees
6 Sept - 7 Sept
Quality Inn Old Saybrook - Westbrook

9. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Egor
Rp1.755.700
Rp2.019.028 total
includes taxes & fees
16 Aug - 17 Aug
Pier Blue Inn Old Saybrook - Essex

10. Zey Hotel

Zey Hotel
Greenport
United States
anna
Rp3.609.967
Rp4.124.388 total
includes taxes & fees
25 Aug - 26 Aug
Zey Hotel

11. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
Rp4.380.094
Rp5.004.217 total
includes taxes & fees
14 Sept - 15 Sept
House on Chase Creek

12. Shorewood Inn

Shorewood Inn
Riverhead
United States
Sheila
Rp2.910.554
Rp3.325.122 total
includes taxes & fees
17 Aug - 18 Aug
Shorewood Inn

13. Clinton Motel

Clinton Motel
Clinton
United States
David
Rp1.408.333
Rp1.619.583 total
includes taxes & fees
2 Sept - 3 Sept
Clinton Motel

14. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
Rp5.588.765
Rp6.385.275 total
includes taxes & fees
23 Aug - 24 Aug
West Neck Guesthouse

15. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Christopher
Rp6.774.260
Rp7.739.593 total
includes taxes & fees
14 Sept - 15 Sept
Sag Harbor Inn

16. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
Rp9.524.614
Rp11.970.031 total
includes taxes & fees
14 Sept - 15 Sept
The Pridwin Hotel

17. Sound View Greenport

Sound View Greenport
Greenport
United States
Yveline
Rp5.010.278
Rp7.251.840 total
includes taxes & fees
9 Sept - 10 Sept
Sound View Greenport

18. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Garvin
Rp3.618.881
Rp4.134.571 total
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Long Island East End

19. American Beech Hotel

American Beech Hotel
Greenport
United States
kerri
Rp7.038.100
Rp8.753.948 total
includes taxes & fees
8 Sept - 9 Sept
American Beech Hotel

20. The Captain Stannard

The Captain Stannard
Westbrook Center
United Kingdom
Jessica
Rp4.170.074
Rp4.628.782 total
includes taxes & fees
13 Sept - 14 Sept
The Captain Stannard
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Stay near popular Southold attractions

Sparkling Pointe

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

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

8.0/10 (4 reviews)
This family-run vineyard crafts sustainable wines in an intimate North Fork setting. Enjoy personalised tastings with garden-to-table pairings on the patio overlooking lush vines.
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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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Sannino's Bella Vita Vineyard

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

Zey Hotel

Zey Hotel

8/10 Good
"Small boutique hotel with great midweek rates. Cool communal areas, and free parking. Bathrooms need a white subway tile update but a great location."
Neil 2-night trip
Posted 7 hours ago
Zey Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Rooms were clean staff helpful would definitely go back"
Frank 2-night trip
Posted 8 hours ago
Saybrook Point Resort & Marina
North Fork Resort

North Fork Resort

10/10 Excellent
"The property was very nice, fire pit, bbq per cabin. Also a toaster oven, microwave, full refrigerator, dishes, utensils, etc. roomy cabin with two bedrooms. Enjoyed our stay here. Thank you!"
mary 2-night trip
Posted 9 hours ago
North Fork Resort
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Booking process was very simple and easy"
Roberto 3-night trip
Posted 11 hours ago
The Atlantic Hotel
Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Rooms have been recently renovated and very clean. Plenty of free parking. The rooms have AC, cable and Roku. Convenient to shopping and splish splash."
JOHN 1-night trip
Posted 13 hours ago
Greenview Inn Riverhead
 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Perfect little spot in Hamptons Bay!"
Jessica 2-night trip
Posted 13 hours ago
Hampton's Vacation Inn
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Nice resort, very convenient. However, a little pricey and every time you turned around there was a gratuity. Food was ok, not great for the price paid though."
Russell 2-night trip
Posted 15 hours ago
Water's Edge Resort & Spa
The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"The hotel was very clean with a lovely environment. The staff (especially at the front desk) were helpful, friendly, polite and very knowledgeable about recommendations for the area. The property was well maintained and the views were beautiful and very accessible to many activities in the area. Looking forward to return in the near future."
Robert 2-night trip
Posted 1 day ago
The Shoals Suites and Slips
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Place was charming and overall beautiful .. everything was wonderful.. definitely will stay again"
Mary 1-night trip
Posted 1 day ago
The Hampton Maid

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Rp1.755.700
Rp2.019.028 total
16 Aug - 17 Aug
includes taxes & fees
8/10 Very good! (1,004 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
Rp2.221.329
Rp2.537.870 total
3 Sept - 4 Sept
includes taxes & fees
Budget Host East End
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
Rp2.887.974
Rp3.299.511 total
27 Aug - 28 Aug
includes taxes & fees
7.4/10 Good! (849 reviews)
Greenview Inn Riverhead
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
Rp3.012.763
Rp3.887.756 total
8 Sept - 9 Sept
includes taxes & fees
9.6/10 Exceptional! (557 reviews)
The Bentley Hotel Southampton
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG

1707 Old Country Rd Riverhead NY
Rp3.843.555
Rp4.391.263 total
8 Sept - 9 Sept
includes taxes & fees
Holiday Inn Express & Suites Riverhead - Long Island by IHG
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
Rp3.513.702
Rp4.459.959 total
8 Sept - 9 Sept
includes taxes & fees
7.2/10 Good! (1,002 reviews)
The Atlantic Hotel

Find out more about Southold

Top reasons to visit Southold

  • Scenic Beaches: Southold boasts stunning beaches perfect for relaxation and coastal strolls.
  • Charming Wineries: Experience renowned local wineries, offering delightful tastings and beautiful vineyard views.
  • Rich Historical Sites: Explore the Southold Historical Museum to immerse yourself in the area's fascinating history.
  • Outdoor Adventures: Enjoy golfing, hiking, and family-friendly activities in picturesque parks.
  • Welcoming Accommodations: Choose from a variety of comfortable hotels catering to all types of travellers.

Find great hotels near Southold

Experience the charm of Southold with a stay in one of its delightful hotels, offering a variety of accommodations to suit every traveller. Whether you're seeking pet-friendly options, family-friendly amenities, or an adventurous getaway, Southold's hotels provide a welcoming atmosphere for a memorable vacation. Discover the best lodging choices in the area, including comfortable hotel rooms and spacious suites, ensuring a relaxing retreat in this picturesque destination.

  • Sound View Greenport: Sound View Greenport offers a delightful beachside retreat just 5km from Southold. This 3.5-star hotel is renowned for its family-friendly atmosphere, providing a range of amenities designed with children in mind, including complimentary cribs and safety features like window guards. Pet lovers will also appreciate the hotel's pet-friendly policy, welcoming dogs and cats with applicable fees. Guests can indulge in stunning views and direct access to the beach, making it an ideal choice for families seeking relaxation and outdoor activities.
  • Sag Harbor Inn: Located 13km from Southold, Sag Harbor Inn is a sophisticated 3.5-star lodging that caters primarily to business travellers. With an impressive guest rating of 9.4 out of 10, it provides a serene and professional environment conducive to work. Guests can expect comfortable accommodations paired with essential business amenities, ensuring a productive stay. The inn’s proximity to local dining and business hubs adds to its appeal, making it a convenient choice for those visiting for work.
  • The Harbor Front Inn: The Harbor Front Inn is a charming 3.5-star hotel situated 6km from Southold, combining a welcoming atmosphere with business-friendly facilities. Rated 8.8 out of 10, this property allows pets, ensuring guests can bring their furry companions along for the stay. The inn features pet-friendly rooms with specified weight limits and fees, making it suitable for pet owners. Its location along the waterfront provides a picturesque backdrop, appealing to both leisure and business visitors looking for a tranquil setting.

Where to stay near Southold

Discover the charm of Southold, New York, a delightful destination for outdoor enthusiasts and those seeking a romantic getaway. Enjoy family-friendly activities under sunny skies, or indulge in the region's rich history and stunning scenery. Explore nearby towns for luxurious experiences and exciting excursions, from vineyard tours to coastal strolls. Southold’s captivating atmosphere makes it an ideal spot for a memorable vacation, blending relaxation and adventure in one beautiful location.

  • Hamptons: Situated approximately 16km from Southold, the Hamptons are renowned for their stunning beaches and vibrant outdoor activities. This picturesque area is particularly popular from June to August, when visitors flock to enjoy its romantic ambience and beach escapades. The Hamptons boast a plethora of attractions including pristine family beaches, tranquil lakes, and top-notch golf courses. Ideal for those seeking both relaxation and adventure, the Hamptons offer a mix of chic eateries and scenic landscapes that make for an unforgettable travel experience.
  • Greenport: Located around 6km from Southold, Greenport is a charming city that attracts visitors year-round, with peak seasons from June to August. Known for its romantic seaside vibe, Greenport is perfect for outdoor enthusiasts and beach lovers alike. The city features lovely family beaches, expansive parks, and recreational areas that invite exploration. Music concerts and local events further enrich the cultural experience, making Greenport a delightful spot for tourists looking to immerse themselves in the local community while enjoying the scenic waterfront.
  • Sag Harbor: Just 13km from Southold, Sag Harbor is a quaint city that offers an enchanting blend of outdoor pursuits and beachside relaxation. With a seasonal influx of visitors peaking during the summer months, Sag Harbor is a favoured destination for those seeking a romantic getaway. The area is dotted with beautiful beaches, family-friendly shores, and serene lakes. Visitors can engage in various activities, including golfing and skiing, while the charming streets are lined with local shops and eateries that reflect the town's rich maritime heritage.

Things to do near Southold

Shopping

In Southold, visit local shops and boutiques for unique gifts and souvenirs. If you're up for a drive, check out the Tanger Outlets in Riverhead, about 19km away, featuring a wide range of brand-name stores and discount shopping options.

Recreation

In Southold, the Aloha Wellness Spa offers rejuvenating treatments with a focus on holistic health, set amidst serene surroundings. Explore the nearby beaches for yoga sessions or strolls along the shore, providing a tranquil escape and a chance to reconnect with nature.

Adventure

At Riverhead Raceway, located 29km from Southold, you can immerse yourself in the thrill of motor racing, experiencing the adrenaline rush of high-speed competition. Meanwhile, Waterford Speedbowl, situated 43km away, offers a vibrant atmosphere for motorsport enthusiasts, where you can enjoy exhilarating races and the excitement of the crowd.

Nightlife

Experience the laid-back vibe at the Southold Fish Market, where you can enjoy fresh seafood and local wines. For a lively atmosphere, visit the Old Mill Inn, offering a selection of craft cocktails and occasional live music, creating a charming evening out in the heart of Southold.

*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 during your visit to Southold, plan your trip between January and March when accommodation prices are lower, especially on Tuesdays. Avoid weekends, particularly Saturdays, for the best rates. Use Expedia’s search tool to filter hotels by budget and location, and consider booking a package deal that combines flights, hotel, and activities for extra savings. Additionally, explore free local activities to enhance your experience without breaking the bank. Being strategic about your travel dates and utilising online tools can significantly reduce your overall expenses.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, including your budget, preferred location, and the type of hotel you desire. For the best prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy savings by combining your Southold hotel reservations with your flights and activities through an Expedia package.

Find the best attractions in and around Southold

Southold is an ideal destination for outdoor and romantic getaways, offering a delightful blend of beach, urban parks, and historical museums. Visitors can explore the scenic Southold Bay and immerse themselves in the rich history at the Southold Historical Museum. This charming locale caters to those seeking a relaxing beach experience, cultural enrichment, and outdoor adventures, ensuring a memorable holiday for all travellers.

  • Harbes Family Farm: Located 16km from Southold, this charming farm offers a delightful experience with its seasonal activities, including fruit picking and hayrides. Visitors can enjoy fresh produce and homemade treats, making it a great spot for families and food lovers alike.
  • Horton Lane Beach: Situated within Southold, Horton Lane Beach provides a serene coastal atmosphere where you can relax and soak up the sun. The sandy shores and gentle waves create a perfect backdrop for a leisurely day by the sea.
  • Orient Point County Park: About 19km from Southold, this urban park features expansive green spaces and scenic views. It’s an ideal location for picnics and outdoor activities, offering a family-friendly environment amidst natural beauty.

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

Travelling to Southold, New York, is convenient via major airports in the region. John F. Kennedy International Airport (JFK) is approximately 124km away, with nearby luxurious options such as The William Vale and Arlo Williamsburg, both rated 5 stars and located 18km from the airport. LaGuardia Airport (LGA) is about 126km from Southold, offering high-end hotels like The Plaza, A Fairmont Hotel, and Hilton Club The Quin New York, each around 5 to 10km from the airport. Newark Liberty International Airport (EWR) is the furthest at 153km, with excellent accommodation options such as The Dominick and Four Seasons Hotel, each situated 14km away.

Frequently asked questions

Where is the best place to stay in Southold?
The Shoals Suites and Slips is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and private balconies. Vine & Sand is another good option for your trip. See all available top hotels, or vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
What's the best dog-friendly accommodation option in Southold?
White Blossom House Inn is a top hotel for people travelling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. See more pet-friendly hotel accommodations in Southold.
What are some accommodation options with pools in Southold?
Vine & Sand: Offers buffet, a seasonal outdoor pool and free self parking. Sound View Greenport and The Atlantic Hotel are a couple of other choices that offer an on-site pool. View all hotels with pools in Southold.
What's it like to stay in Southold?
Visitors can enjoy all that Southold has to offer, including the wineries, beaches and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 141 hotels and other accommodation options to choose from. Find out more about Southold.
What should I do while I'm visiting Southold?
The picturesque setting of McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Sparkling Pointe and Mattebella Vineyards. Take a look at what more there is to see and do in Expedia's Southold guide.
What's the best way to get around Southold?
To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.
What's the weather like in Southold?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.

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