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Our top choices for Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (271 reviews)
"Great a accomodation"
United States
Rutanya
$267 nightly
The price is $302
May 25 - May 26
Total with taxes and fees
The Shoals Suites and Slips

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (648 reviews)
"Clean rooms, great continental breakfast. Was upgraded to waterfront room!!"
United States
Noreen
$376 nightly
The price is $429
May 26 - May 27
Total with taxes and fees
Sound View Greenport

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (603 reviews)
"Friendly staff clean rooms and very nice views of the harbor. Breakfast was a nice touch. Will stay again."
United States
ray
$294 nightly
The price is $336
May 26 - May 27
Total with taxes and fees
The Harbor Front Inn

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (153 reviews)
"Lovely lodging"
United States
Timothy
$397 nightly
The price is $453
May 27 - May 28
Total with taxes and fees
Silver Sands Motel & Beach Bungalows

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very Good, (783 reviews)
"Every thing was amazing food and drinks to the fire pits on the terrace area"
United States
John
$662 nightly
The price is $756
May 31 - Jun 1
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
$407 nightly
The price is $465
May 28 - May 29
Total with taxes and fees
Vine & Sand

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
"Beautiful, calm and serene. What a nostalgic experience. We’re going back next weekend. A perfect weekend getaway from manhattan "
United States
Rita
$371 nightly
The price is $424
May 28 - May 29
Total with taxes and fees
The Pridwin Hotel

Oyster Estate

Oyster Estate
2.0 star property
Greenport
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
Oyster Estate

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (182 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
$371 nightly
The price is $418
May 25 - May 26
Total with taxes and fees
The Menhaden

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (306 reviews)
"amazing stay! "
United States
Lauren
$180 nightly
The price is $206
May 25 - May 26
Total with taxes and fees
Zey Hotel

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (615 reviews)
"Beautiful hotel facing the harbor with courteous service and staff. "
United States
Alphonso
$315 nightly
The price is $360
May 25 - May 26
Total with taxes and fees
Sag Harbor Inn

The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (13 reviews)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and Breakfast

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (200 reviews)
"Great location! Very clean! "
United States
Elizabeth
$310 nightly
The price is $354
May 25 - May 26
Total with taxes and fees
American Beech Hotel

Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast
3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12 reviews)
"Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!"
United States
Anthony
Harbor Knoll Bed & Breakfast

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (37 reviews)
"Always a sold stay on Shelter Island"
United States
Peter
$425 nightly
The price is $486
May 25 - May 26
Total with taxes and fees
The Chequit

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (25 reviews)
"Excellent host! Extremely helpful and accommodating. Outstanding breakfast."
United States
Pat
$503 nightly
The price is $575
May 29 - May 30
Total with taxes and fees
Stirling House Bed & Breakfast

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very Good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
$219 nightly
The price is $250
May 31 - Jun 1
Total with taxes and fees
West Neck Guesthouse

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,002 reviews)
$264 nightly
The price is $304
May 25 - May 26
Total with taxes and fees
Water's Edge Resort & Spa

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
$825 nightly
The price is $943
Jun 10 - Jun 11
Total with taxes and fees
Faraway Sag Harbor

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (57 reviews)
"One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try."
United States
Joseph
$201 nightly
The price is $230
Jun 3 - Jun 4
Total with taxes and fees
Shelter Island House
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Stay near popular Southold attractions

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.

Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

More cheap stays in Southold

Hotels in Southold with star-rating

Find out more about Southold

Top reasons to visit Southold

  • Stunning Beaches: Southold features serene beaches perfect for relaxation and scenic views.
  • Outdoor Adventures: Enjoy golf, water rides, and unique oyster tours for an exciting experience.
  • Rich History: Explore local museums and historical sites that showcase the area's heritage.
  • Charming Vineyards: Discover nearby vineyards offering tastings and picturesque landscapes.
  • Diverse Accommodations: Choose from pet-friendly options, cozy hotels, and agritourism properties for a perfect stay.

Find great hotels near Southold

Explore a variety of hotel accommodations in Southold, New York, where you can find the ideal lodging for your getaway. Whether you're seeking pet-friendly options, adventure-filled experiences, or a family-friendly atmosphere, Southold offers a range of choices, including charming agritourism properties and cozy hotels. Enjoy a relaxing stay near the beach and discover all that this beautiful area has to offer.

  • Sound View Greenport: Nestled just 3 miles from Southold, Sound View Greenport is a charming 3.5-star hotel with a guest rating of 8.4. This beachfront property is perfect for families and pet lovers, offering direct beach access and a range of child-friendly amenities, including free cribs and window guards for safety. The hotel's pet policy allows dogs and cats, making it an ideal spot for those traveling with furry companions. Enjoy a relaxing vacation with family while soaking up the sun on the beach.
  • Sag Harbor Inn: Located 8 miles from Southold, Sag Harbor Inn boasts a stellar 3.5-star rating and an impressive guest rating of 9.4. This property caters primarily to business travelers, providing a comfortable and professional atmosphere. With convenient amenities and a focus on service, guests can expect a productive stay while enjoying the charming surroundings of Sag Harbor. Whether you are in town for meetings or exploring the local area, this inn offers a welcoming retreat.
  • The Harbor Front Inn: Just 4 miles from Southold, The Harbor Front Inn is a delightful 3.5-star property with a guest rating of 8.8. This inn is perfect for both business travelers and pet owners, allowing pets in select rooms for an additional fee. With a focus on comfort and convenience, guests can take advantage of the inn's proximity to local attractions while enjoying spacious accommodations designed for relaxation. Experience the best of both worlds with a balance of work and leisure at this inviting location.

Where to stay near Southold

Southold, New York, offers a perfect blend of outdoor adventures and romantic getaways. Enjoy family-friendly activities in the sunny weather while exploring the scenic coastline and charming vineyards. Nearby, you can discover luxurious accommodations and historical sites that enrich your experience. Don't miss the chance to indulge in local excursions that highlight the area's natural beauty and vibrant community atmosphere. Southold is truly a hidden gem for travelers seeking relaxation and exploration.

  • Hamptons: Located a mere 10 miles from Southold, the Hamptons are a quintessential summer getaway, famed for their stunning beaches and outdoor activities. During peak season from June to August, this area buzzes with visitors seeking romantic escapes and sun-soaked adventures. Explore the picturesque coastline, indulge in world-class dining, or tee off at one of the region’s renowned golf courses. Whether you’re lounging on the beach or enjoying a sunset by the lake, the Hamptons offer a blend of relaxation and excitement that makes it a must-visit destination.
  • Greenport: Just 4 miles away from Southold, Greenport is a charming city that captures the essence of coastal living. This vibrant town sees its highest visitor numbers from June to August, attracting couples and families alike who are drawn to its outdoor allure and beach experiences. With an array of recreational areas, music concerts, and beautiful parks, Greenport is perfect for those who appreciate a lively atmosphere. Stroll along the waterfront, savor fresh seafood, and immerse yourself in the local culture, making your visit an unforgettable one.
  • Noyack: Situated 7 miles from Southold, Noyack is a serene village that offers a peaceful retreat for outdoor enthusiasts and beach lovers. Visitors flock here in the summer months, from June to August, seeking romantic getaways and nature-filled adventures. With access to golf courses, ski options, and pristine beaches, Noyack is ideal for both relaxation and recreation. Enjoy family-friendly activities at the local parks or unwind by the tranquil lakes, creating lasting memories in this idyllic setting.

Things to do in Southold

Southold, New York, offers a delightful blend of outdoor and romantic activities perfect for vacationers. Enjoy a round of golf at local courses or relax in scenic recreational areas. Don't miss out on unique oyster tours and thrilling water rides at nearby Splish Splash. With its serene beaches, Southold is an ideal destination for those looking to unwind and explore the natural beauty of the area.

Shopping

In Southold, visit local shops for unique gifts and souvenirs, such as the Southold General Store for charming finds. If you're up for a drive, check out the Tanger Outlets in Riverhead, about 12 miles away, featuring a wide range of brand-name outlet stores.

Recreation

Calm Waters Wellness Spa offers rejuvenating treatments like massages and facials, perfect for relaxation. For outdoor enthusiasts, Southold’s beaches provide stunning views and opportunities for kayaking and paddleboarding, creating a peaceful environment to unwind and connect with nature.

Adventure

Explore the scenic beauty of Southold by kayaking in the tranquil waters of Peconic Bay. Experience the thrill of paddleboarding along the coastline or embark on a bike tour through charming vineyards. Enjoy hiking at Inlet Pond County Park, where stunning views and nature trails await.

Nightlife

In Southold, the nightlife is relaxed yet vibrant, with cozy bars like The Southold Fish Market offering fresh seafood and local wines. For a fun evening, visit the nearby Greenport Village, where lively music and charming pubs create a welcoming atmosphere for all visitors.

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

Booking tips and Expedia advantages for Southold

  • 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 makes it easy to choose based on your budget, desired location, and other preferences. You can arrange your results to display the lowest prices first, helping you find the most affordable hotels right away. Additionally, you can refine your choices by hotel category—if you check the Eco-certified option, you'll see a selection of sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Southold with your flights and activities by booking a package through Expedia.

Find the best attractions in and around Southold

Southold offers a delightful blend of outdoor adventures, romantic spots, and entertainment options, making it perfect for vacationers. Visitors can explore beautiful beaches, rich history at local museums, and enjoy leisurely strolls in urban parks. With a focus on culture and outdoor experiences, Southold is an ideal destination for travelers seeking relaxation and exploration in a charming setting.

  • Horton Lane Beach: Experience the quintessential beach vibes at Horton Lane Beach, where you can relax on the sandy shores, soak up the sun, and enjoy the tranquil atmosphere. It's a perfect spot for a leisurely day by the water.
  • Orient Point County Park: Located 12 miles from Southold, this urban park offers a family-friendly environment with plenty of outdoor activities. Enjoy hiking trails, picnic areas, and breathtaking views, making it an ideal spot for a fun day out with loved ones.
  • Horton Point Park: Immerse yourself in history at Horton Point Park, home to a charming historic lighthouse. The park showcases rich cultural heritage and provides stunning views of the surrounding coastline, perfect for history buffs and nature lovers alike.

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.

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

Traveling to Southold, New York, is convenient with major airports nearby. John F. Kennedy International Airport (JFK) is 77 miles away and offers luxury accommodations like Arlo Williamsburg and The William Vale, both 11 miles from the airport. Newark Liberty International Airport (EWR) is 95 miles away, with upscale options such as The Dominick and Four Seasons Hotel New York Downtown, both 9 miles from EWR. LaGuardia Airport (LGA) is located 78 miles from Southold, featuring nearby hotels like The Plaza and The Pierre, each 5 miles from the airport, with various transportation services available. These options ensure a comfortable start to your vacation.

Why book with Expedia?

  • Flexible booking

    On Expedia, you can find plenty of hotels with flexible cancellation in Southold using the “Fully refundable property” search filter. Just be sure to always double-check each hotel's cancellation policy before booking.

  • Book now and pay later

    With countless book now, pay later options, there's no need to wait till payday to grab a deal. Use the “Reserve now, pay later” search filter to view all properties available with this payment option in Southold.

  • Hotel comparison

    Thanks to the handy “Compare properties” tool on Expedia, you can compare hotels in Southold side by side with just a few clicks.

  • Member prices

    Join Expedia's loyalty program, One Key, for free and unlock Member Prices and rewards on select hotels worldwide. Simply log in when you search and look out for the blue savings label.

Frequently asked questions

What is the best area to stay in Southold?
The best area to stay in Southold is along Main Road (Route 25) or near the waterfront, offering convenient access to local attractions and the serene atmosphere of the North Fork.

For those seeking a quintessential North Fork experience, focusing on accommodations directly on or just off Main Road (Route 25) in Southold offers direct access to the region's renowned vineyards, farm stands, and local eateries. This central artery of Southold is lined with charming historic homes and provides a straightforward route to explore the area's agricultural bounty and coastal beauty. Couples often appreciate this area for its easy access to wine tastings and farm-to-table dining.

Travelers looking for a tranquil retreat will find accommodations closer to the waterfront, such as those near Southold Bay or Peconic Bay, particularly appealing. These areas provide opportunities for water activities, stunning views, and a quieter setting away from the main road.
What are the best hotels in Southold that travelers recommend?
Two of the best hotels in Southold that receive consistently high recommendations from travelers are The Shoals Suites and Slips and Vine & Sand.

The Shoals Suites and Slips is a 3.5-star hotel with an exceptional 9.6 rating. Guests often comment on the new and clean rooms, the beautiful and great location, and the super comfortable beds. The hotel offers a winery with a tasting room, premium bedding, bathrobes, and champagne service.

Another highly recommended option is the 3-star Vine & Sand, which also has a 9.6 rating. This hotel is praised for its lovely rooms and offers amenities such as Egyptian cotton sheets, bathrobes, designer toiletries, and a rainfall showerhead. Guests can enjoy a complimentary buffet breakfast and it is conveniently located just 0.4 miles from the Custer Institute and Observatory.

Both hotels are known for providing an excellent guest experience with luxurious touches.
What are the best family hotels in Southold?
For a highly-rated family-friendly hotel in Southold, The Shoals Suites and Slips is an excellent choice.

This 3.5-star hotel boasts an impressive 9.6 rating, with guests consistently praising its new and clean rooms, beautiful and spacious suites, and super comfortable beds. The staff are frequently described as nice and welcoming, contributing to a pleasant stay. Its beautiful location is also a highlight for many visitors. For families interested in local experiences, the hotel offers a winery with a tasting room, vineyard, private tours, and release events. Cribs are also available free of charge, adding to its appeal for families traveling with young children.
What hotels in Southold offer free breakfast?
For hotels in Southold that offer complimentary breakfast, Vine & Sand is an excellent choice.

This 3-star hotel, with an outstanding 9.6 rating, provides a free buffet breakfast daily. Guests consistently describe the rooms as lovely. Additionally, the hotel offers free WiFi and free self-parking. It is conveniently located near the Custer Institute and Observatory, just 0.4 miles away, and Sannino's Bella Vita Vineyard, 0.9 miles away. Find more hotels with free breakfast in Southold
What are the top pet-friendly hotels in Southold?
For top pet-friendly accommodation in Southold, consider the Cozy Long Island Escape.

This hotel, with an outstanding 9.6 rating, is an excellent choice for travelers with pets, as both dogs and other pets are permitted. It offers a kitchen, a deck or patio, and a secured yard, providing ample space and convenience for both guests and their animal companions. The Cozy Long Island Escape is also conveniently located near the Custer Institute and Observatory and Horton Lane Beach. See more pet-friendly hotels in Southold
What are the best budget hotels in Southold?
For a highly-rated budget hotel in Southold, consider Vine & Sand.

The 3-star Vine & Sand, with an excellent 9.6 rating, offers a comfortable stay with complimentary WiFi, free buffet breakfast, and free self-parking. Guests consistently describe the rooms as lovely. This hotel is conveniently located near the Custer Institute and Observatory, just 0.4 miles away, and Sannino's Bella Vita Vineyard, which is 0.9 miles from the property. View all budget hotels in Southold
What are the most romantic hotels in Southold for couples?
For a romantic stay in Southold, The Shoals Suites and Slips is an excellent choice for couples.

This 3.5-star hotel, with an outstanding 9.6 rating, offers couples dining experiences and features a winery with a tasting room, vineyard, and options for private tours and release events. Guests consistently praise the beautiful and clean rooms, the super comfortable beds, and the welcoming staff. Its beautiful location is also highlighted, and it is conveniently located just 0.4 miles from The Old Field Vineyards.
What are the best hotels in Southold near Custer Institute and Observatory?
For hotels in Southold near Custer Institute and Observatory, consider Vine & Sand, or the vacation rental known as Great Location.. Walk to Town & Train..

The 3-star Vine & Sand, with an excellent 9.6 rating, is conveniently located just 0.4 miles from Custer Institute and Observatory. Guests appreciate the complimentary breakfast, including a buffet option, and the free WiFi. It's also noted for its lovely rooms.

Another highly-rated option is the vacation rental Great Location.. Walk to Town & Train.., boasting a superb 10.0 rating. This accommodation is located 1.1 miles from the observatory and offers amenities such as a kitchen, a secured yard, and a deck or patio, providing a comfortable stay for families.
When is the best time to go to Southold?
The best time to visit Southold is during the late spring and early fall, particularly from May to June and September to October, for pleasant weather and fewer crowds.

Late spring, particularly June, offers comfortable temperatures ranging from the high 60s to mid-70s Fahrenheit, making it ideal for outdoor activities like exploring vineyards, visiting beaches, and cycling. The seasonal businesses are typically open, but the summer rush hasn't fully begun, allowing for a more relaxed experience. Couples looking for a quiet getaway will appreciate the serene atmosphere before the peak season.

Early fall, specifically September and October, is another excellent time to visit. The weather remains mild, with temperatures often in the 60s, and the fall foliage adds a scenic backdrop to the North Fork's vineyards and farms. This period is great for enjoying harvest festivals, wine tastings, and farm-to-table dining without the larger crowds of summer.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Southold.
How can I save on a Southold hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Southold hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Southold hotel?
Prices for hotels in Southold often vary, but you can find a great deal from $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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