Southold Holiday Rentals, New York: Private House Rentals

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

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Our top choices for Southold hotels

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

1. The Shoals Suites and Slips

Southold

Melissa

฿6,670

฿8,447 total

includes taxes & fees

1 Oct - 2 Oct

A deck with outdoor seating, overlooking a body of water with a sunset view.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

2. The Pridwin Hotel

Shelter Island Heights

Anna

฿16,755

฿21,057 total

includes taxes & fees

14 Sept - 15 Sept

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

A seaside restaurant with outdoor seating, a deck, and a view of the ocean.

A coastal building with large windows, a deck, and a view of the sea at sunset.

3. Sound View Greenport

Greenport

Irene

฿8,780

฿10,975 total

includes taxes & fees

1 Oct - 2 Oct

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

A restaurant with a signboard listing its hours of operation.

A bar area with stools, a shelf with glasses, and decorative plants.

4. Zey Hotel

Greenport

Renee

฿5,577

฿6,372 total

includes taxes & fees

14 Sept - 15 Sept

5. Cliffside Resort Condominiums

Greenport

Christine

฿9,549

฿13,856 total

includes taxes & fees

5 Oct - 6 Oct

A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.

A grassy area with trees and a view of a body of water.

A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.

6. Silver Sands Motel & Beach Bungalows

Greenport

Sirikhwan

฿10,741

฿12,272 total

includes taxes & fees

12 Oct - 13 Oct

A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

A modern bar area with black bar stools, a counter with a variety of bottles, and hanging green plants in wire baskets.

A modern reception area with a staircase, a framed artwork, and a reception desk with "THE MENHADEN" signage.

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

7. The Menhaden

Greenport

Lisa

฿12,186

฿15,245 total

includes taxes & fees

17 Sept - 18 Sept

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

A dining area with a round table, two chairs, a framed artwork, a vase with flowers, a bottle, and books.

A residential area with a large building, a swimming pool, and a dock extending into a body of water.

8. The Harbor Front Inn

Greenport

Michael

฿8,596

฿10,765 total

includes taxes & fees

4 Oct - 5 Oct

A modern house with a deck, outdoor seating, and a fire pit.

A modern kitchen with a stainless steel sink, white cabinets, and a blue-tiled backsplash.

A tented accommodation with a bed, television, and a small table with a chair.

A modern living room with a sofa, a dining table, and a kitchen area in the background.

9. North Fork Resort

Greenport

Lisa

฿10,619

฿12,132 total

includes taxes & fees

21 Sept - 22 Sept

A waterfront property with a large house, multiple boats docked, and lush greenery.

A hotel lobby with a sofa, chairs, tables, and a large window.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

10. Sag Harbor Inn

Sag Harbor

Loretta

฿10,708

฿12,234 total

includes taxes & fees

4 Oct - 5 Oct

A parking lot with a building in the background.

A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

A motel with a large parking lot and multiple rooms.

11. Clinton Motel

Clinton

Selena

฿2,578

฿2,965 total

includes taxes & fees

14 Sept - 15 Sept

12. Shelter Island House

Shelter Island Heights

Dorothy

฿6,651

฿7,599 total

includes taxes & fees

4 Oct - 5 Oct

A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

A building with a red facade, a green tree in front, and a sign reading "OPENSPACE".

A modern lounge area with a curved sofa, round coffee tables, and a large potted plant.

A reception desk with a white backdrop, surrounded by various plants and a modern pendant light.

13. American Beech Hotel

Greenport

Mary

฿10,272

฿13,058 total

includes taxes & fees

21 Sept - 22 Sept

A poolside area with lounge chairs and yellow umbrellas.

A cozy interior with a bar area, seating, and a fireplace.

A cozy interior with a wooden bench, a sofa, and a bar area.

14. Oyster Estate

Greenport

Jenny

฿11,369

฿14,325 total

includes taxes & fees

5 Oct - 6 Oct

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

15. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Michael

฿3,343

฿3,844 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen area with a long counter, various appliances, and a sign that reads "Delight in the day".

A reception area with a wooden reception desk, a green rug, and a wall-mounted abstract art piece.

A hotel room with a bed, a desk, a chair, a TV, and a door.

A hotel with a 'spark by Hilton' sign, a parking lot, and a covered parking area.

16. Spark by Hilton Guilford

Guilford

Stacy

฿3,794

฿4,363 total

includes taxes & fees

21 Sept - 22 Sept

A train traveling along a river with autumn foliage in the background.

A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

17. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

฿2,697

฿3,101 total

includes taxes & fees

17 Sept - 18 Sept

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

18. Water's Edge Resort & Spa

Westbrook Center

DONNA

฿5,924

฿7,383 total

includes taxes & fees

7 Oct - 8 Oct

A serene landscape with a calm body of water reflecting trees with autumn foliage.

A sign for 'House on Chase Creek' with a duck illustration.

A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

19. House on Chase Creek

The Heights

Calvin

฿7,115

฿8,129 total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bed, bedside tables, a lamp, a window, and a door.

A beach with a wooden walkway along the shore, calm water, and a sunset sky.

A backyard with a large chessboard, outdoor furniture, and a house.

A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

20. West Neck Guesthouse

Shelter Island Heights

Allie

฿10,361

฿11,838 total

includes taxes & fees

15 Sept - 16 Sept

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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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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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Horton Point Park

9.4/10 (3 reviews)

This 1857 lighthouse stands sentinel over Long Island Sound, housing a nautical museum filled with maritime artefacts. 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 personalised 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.

Top Southold Hotel Reviews

Greenview Inn Riverhead

8/10 Good

"For a relatively "affordable" ($380!!!) place to stay for one night during the highly in-demand Labor Day weekend on the East End of Long Island, the Greenview Inn was the closest we could get to what we were looking for: A clean bed to lay our heads at the end of a busy wedding reception. Thank goodness we were able to pay with OneKey Cash. The room was relatively clean, and appeared to have been recently renovated. The sheets felt slightly damp, perhaps from humidity, perhaps because they had been insufficiently dried during laundering. Additionally, there were a couple of small flies buzzing about as we tried to get to bed. We were on the first floor, so privacy and noise mitigation were a key concern. The thin curtains barely did the job of covering the front windows, and had to be jury-rigged to ensure that the air conditioner didn't blow them away from the window. Heavier curtains set within the window frame would be a nice upgrade. We did not make much use of any amenities on the premises, so we cannot speak to any on-site coffee or breakfast option. We did appreciate the property's beautiful vista on the Peconic River however. The property's dock is sorely in need of repair or removal, but the waterfront appears to be an unrecognized asset for the property. There should be kayaks/canoes available for guests whether for free or by rental. All in all, grateful for a relatively clean and quiet place to stay the night, but there is absolutely room for improvement."

Water's Edge Resort & Spa

10/10 Excellent

"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Deverian actualizar las tv’s"

The Harbor Front Inn

10/10 Excellent

"This was our first trip to Greenport and we had a fabulous stay. The hotel was perfectly located downtown."

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!"

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."

Zey Hotel

10/10 Excellent

"Such an amazing hotel to stay for the weekend"

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."

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

฿2,697

฿3,101 total

17 Sept - 18 Sept

includes taxes & fees

8/10 Very good! (1,003 reviews)

Budget Host East End

30 Lake Avenue Riverhead NY

฿2,941

฿3,361 total

14 Sept - 15 Sept

includes taxes & fees

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

฿3,343

฿3,844 total

4 Oct - 5 Oct

includes taxes & fees

7.8/10 Good! (1,005 reviews)

The Atlantic Hotel

1655 County Road 39 Southampton NY

฿3,941

฿5,329 total

1 Oct - 2 Oct

includes taxes & fees

7.2/10 Good! (1,004 reviews)

Holiday Inn Express & Suites Riverhead - Long Island by IHG

1707 Old Country Rd Riverhead NY

฿5,387

฿6,155 total

14 Oct - 15 Oct

includes taxes & fees

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

฿6,990

฿7,986 total

13 Oct - 14 Oct

includes taxes & fees

Find out more about Southold

Top reasons to visit Southold

Picturesque Beaches: Southold boasts stunning beaches with serene waters, perfect for relaxation and seaside activities.
Charming Wineries: Explore local wineries offering delightful tours and tastings, showcasing the region's rich viticulture.
Historical Gems: Visit the Southold Historical Museum to gain insights into the area's fascinating past.
Scenic Golf Courses: Enjoy a round of golf amidst beautiful landscapes, catering to enthusiasts of all skill levels.
Quaint Accommodations: Choose from charming bed and breakfasts and unique agritourism stays for a memorable experience.

Find great hotels near Southold

Discover a delightful range of hotel accommodations in Southold, New York, perfect for adventurous travellers and families alike. From charming bed and breakfasts to unique agritourism properties, there’s something to suit every preference. Whether you’re seeking pet-friendly options or spacious hotel suites, Southold offers a variety of choices to ensure a memorable stay in this picturesque destination.

Sound View Greenport: Nestled a mere 5km from Southold, Sound View Greenport is a charming 3.5-star hotel with a guest rating of 8.4 out of 10. This property boasts a distinctive beach theme, providing direct access to the shoreline for relaxation and recreation. Ideal for families and business travellers alike, the hotel features child-friendly amenities such as window guards and complimentary cribs. Guests can enjoy the scenic views while indulging in the tranquil atmosphere that this coastal retreat offers.
Sag Harbor Inn: Located approximately 13km from Southold, Sag Harbor Inn is a refined 3.5-star accommodation with an impressive guest rating of 9.4 out of 10. With a focus on business travel, this inn provides a sophisticated environment for professionals seeking convenience and comfort. Its strategic location allows for easy access to local amenities and attractions, making it a suitable choice for those who value both productivity and leisure during their stay.
The Harbor Front Inn: Just 6km from Southold, The Harbor Front Inn offers a welcoming atmosphere with a guest rating of 8.8 out of 10. This 3.5-star property is particularly appealing to pet owners, as it accommodates pets and provides specific amenities to ensure a comfortable stay for all guests. Whether you are travelling for business or leisure, you'll appreciate the combination of modern conveniences and the charming surroundings that enhance your experience.

Where to stay near Southold

Southold, New York, offers a delightful mix of outdoor adventures and romantic escapades. Visitors can bask in the sunny weather while exploring the charming local scenery, making it ideal for family-friendly excursions. Nearby attractions provide a glimpse into the region's rich history and luxury experiences, ensuring a memorable stay. Whether you're indulging in the area's quaint ambience or embarking on exciting excursions, Southold is a perfect destination for an unforgettable getaway.

Hamptons: Located 16km from Southold, the Hamptons is a renowned summer destination known for its beautiful beaches and outdoor activities. This area transforms into a vibrant hub from June to August, attracting visitors seeking romantic getaways and sun-soaked days. Beyond the sandy shores, you can enjoy world-class golf courses and ski fields, making it a versatile spot for various interests. Don't miss the picturesque local landmarks, including family-friendly beaches and tranquil lakes that complement the scenic beauty of the Hamptons.
Greenport: Just 6km away from Southold, Greenport is a charming city that offers a delightful blend of outdoor adventure and romantic experiences. The peak tourist season runs from June to August, drawing in those eager to explore its lovely beaches and parks. Visitors can engage in numerous activities such as golfing and attending music concerts in the area. Greenport's quaint atmosphere is perfect for leisurely strolls along the beach or enjoying the local parks, making it a wonderful place to unwind and connect with nature.
Sag Harbor: Situated 13km from Southold, Sag Harbor is another picturesque city that captures the essence of coastal living. Like its counterparts, Sag Harbor experiences a seasonal influx of visitors, especially from June to August. The area is perfect for outdoor enthusiasts, offering stunning beaches, golf courses, and opportunities for skiing. With its charming lakes and family-friendly beaches, Sag Harbor provides an idyllic setting for relaxation and romance, making it an excellent addition to your travel itinerary.

Things to do near Southold

Shopping

In Southold, you can explore charming local shops for unique gifts and souvenirs. If you're up for a drive, consider visiting the Tanger Outlets in Riverhead for a wider selection of brand-name items and great deals, located around 19km away.

Recreation

Explore the serene surroundings at The Wellhouse, where you can indulge in yoga classes and rejuvenating spa treatments. For outdoor relaxation, visit Southold Town Beach, offering a tranquil setting for sunbathing and leisurely strolls along the shore, perfect for unwinding amidst nature.

Adventure

Experience the thrill of racing at Riverhead Raceway, located 29km from Southold, where you can enjoy exciting motor racing events in a vibrant atmosphere. Alternatively, head to Waterford Speedbowl, situated 43km away, for more exhilarating racing action amidst an adventurous setting.

Nightlife

In Southold, the nightlife is charming and relaxed, featuring venues like The Southold Fish Market, where you can enjoy fresh seafood and casual drinks. Nearby, the Greenport Village offers quaint bars and live music, creating a delightful atmosphere for evening strolls and socialising with locals.

*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 is perfect for outdoor and romantic getaways, offering a blend of entertainment and cultural experiences. Visitors can enjoy beautiful beaches, urban parks, and the Southold Historical Museum, along with the scenic Southold Bay. Whether you seek relaxation by the shore or a glimpse into local history, Southold caters to all your vacation desires.

North Main Street Historic District: Explore this charming neighbourhood, located 19km from Southold, where historic architecture meets a vibrant local atmosphere. Wander through boutique shops and delightful eateries, immersing yourself in the rich history of the area.
Horton Lane Beach: Enjoy the serene coastal vibes at Horton Lane Beach, situated within Southold. This picturesque beach offers a perfect spot for relaxation, sunbathing, and leisurely strolls along the shore, making it an ideal retreat for beach lovers.
Orient Point County Park: Just 19km away, this urban park is a wonderful destination for families and outdoor enthusiasts. With scenic trails and recreational areas, you can appreciate nature while enjoying activities such as picnicking and birdwatching.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	35.8°F (2.1°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	39.7°F (4.3°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Average	Average
October	59.7°F (15.4°C)	Light Rain	Mostly Sunny	Average	Average
November	49.6°F (9.8°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	42.1°F (5.6°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

The nearest major airports for your trip to Southold

Reaching Southold, New York, is convenient via several major airports. New York, NY (JFK-John F. Kennedy Intl.) is located 124km away, with excellent hotel options such as The William Vale and Arlo Williamsburg, both 18km from the airport. Providence, RI (PVD-T.F. Green) is 111km from Southold, and nearby hotels include the Omni Providence Hotel and Graduate by Hilton Providence, each 11km from the airport. Lastly, Newark Liberty Intl. Airport (EWR) is 153km away, with luxurious accommodation options like The Dominick and Four Seasons Hotel New York Downtown, situated 14km from the airport. Each airport provides easy access to Southold, enhancing your travel experience.

Frequently asked questions

Where is the best place to stay in Southold?

The Shoals Suites and Slips is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and private balconies. Other good choices for your stay in 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, 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?

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 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 Croteaux 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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Be picky

Go beyond your typical stay in Southold

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Our top choices for Southold hotels

1. The Shoals Suites and Slips

2. The Pridwin Hotel

3. Sound View Greenport

4. Zey Hotel

5. Cliffside Resort Condominiums

6. Silver Sands Motel & Beach Bungalows

7. The Menhaden

8. The Harbor Front Inn

9. North Fork Resort

10. Sag Harbor Inn

11. Clinton Motel

12. Shelter Island House

13. American Beech Hotel

14. Oyster Estate

15. Quality Inn Old Saybrook - Westbrook

16. Spark by Hilton Guilford

17. Pier Blue Inn Old Saybrook - Essex

18. Water's Edge Resort & Spa

19. House on Chase Creek

20. West Neck Guesthouse

Stay near popular Southold attractions

Sparkling Pointe

Croteaux Vineyards

Sannino's Bella Vita Vineyard

Horton Point Park

Osprey's Dominion

Horton Lane Beach

Mattebella Vineyards

The Old Field Vineyards

Learn more about Southold

Top Southold Hotel Reviews

Greenview Inn Riverhead

Water's Edge Resort & Spa

Pier Blue Inn Old Saybrook - Essex

The Harbor Front Inn

The Atlantic Hotel

North Fork Resort

Zey Hotel

Faraway Sag Harbor

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Budget Host East End

Quality Inn Old Saybrook - Westbrook

The Atlantic Hotel

Holiday Inn Express & Suites Riverhead - Long Island by IHG

The Hampton Maid

Find out more about Southold

Top reasons to visit Southold

Find great hotels near Southold

Where to stay near Southold

Things to do near Southold

Find the best attractions in and around Southold

Best time to go to Southold

The nearest major airports for your trip to Southold

Frequently asked questions

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