Best Southold Hotels in 2026 from HK$622 - Fully Refundable Options

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

A storefront with a sign reading "THE SHOALS".

1. The Shoals Suites and Slips

Southold

Melissa

HK$1,583

HK$2,005 total

includes taxes & fees

1 Oct - 2 Oct

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

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

A beach bar with wooden chairs and a small table, overlooking the sea.

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

2. Sound View Greenport

Greenport

Irene

HK$1,941

HK$2,442 total

includes taxes & fees

6 Oct - 7 Oct

3. Cliffside Resort Condominiums

Greenport

Christine

HK$1,850

HK$2,984 total

includes taxes & fees

25 Oct - 26 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.

4. Silver Sands Motel & Beach Bungalows

Greenport

Keith

HK$2,549

HK$2,913 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

A modern bedroom with two beds, a sofa, a coffee table, and a potted plant.

5. Zey Hotel

Greenport

Renee

HK$1,324

HK$1,512 total

includes taxes & fees

12 Oct - 13 Oct

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 vase with flowers and a bowl on a dresser against a wall.

A large building with multiple floors, surrounded by a residential area with houses and a body of water.

6. The Harbor Front Inn

Greenport

Jordan

HK$1,758

HK$2,232 total

includes taxes & fees

26 Oct - 27 Oct

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

A modern living room with a grey sofa, black and white patterned rug, and a coffee table.

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

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

7. The Menhaden

Greenport

Lisa

HK$2,478

HK$3,145 total

includes taxes & fees

30 Sept - 1 Oct

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

An outdoor dining area with tables and chairs, string lights, and hanging lanterns.

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.

8. American Beech Hotel

Greenport

Mary

HK$1,796

HK$2,366 total

includes taxes & fees

1 Oct - 2 Oct

An outdoor patio area with string lights, tables, chairs, and a fire pit.

A modern hotel room with a large bed, a sofa, a chair, a small table, and a mirror.

A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.

A staircase with wooden balusters and a white wall.

9. The Chequit

The Heights

Kristin

HK$1,624

HK$1,855 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

10. North Fork Resort

Greenport

Harold

HK$2,090

HK$2,387 total

includes taxes & fees

4 Oct - 5 Oct

11. Shelter Island House

Shelter Island Heights

Dorothy

HK$1,579

HK$1,804 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

12. Sag Harbor Inn

Sag Harbor

Terri

HK$1,953

HK$2,232 total

includes taxes & fees

30 Oct - 31 Oct

A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

A cozy bedroom with a wooden headboard, a bedside table with a lamp, a vase with flowers, and a bed with a floral bedspread.

A sign for Oyster Estate with a tree in the background.

A poolside area with lounge chairs and yellow umbrellas.

13. Oyster Estate

Greenport

Elizabeth

HK$2,354

HK$2,965 total

includes taxes & fees

21 Oct - 22 Oct

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

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.

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

14. House on Chase Creek

The Heights

Calvin

HK$1,689

HK$1,929 total

includes taxes & fees

5 Oct - 6 Oct

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

A living room with a beige sofa, a coffee table, and a dining table set with plates and glasses.

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.

15. West Neck Guesthouse

Shelter Island Heights

Allie

HK$2,459

HK$2,810 total

includes taxes & fees

1 Oct - 2 Oct

A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

A modern bar area with a long counter, multiple seating options, and a variety of bottles and glasses on shelves.

A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

16. Hyatt Place Long Island East End

Riverhead

Veronica

HK$1,224

HK$1,398 total

includes taxes & fees

14 Oct - 15 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 two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

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

17. Clinton Motel

Clinton

Selena

HK$612

HK$704 total

includes taxes & fees

30 Sept - 1 Oct

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.

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

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

18. Water's Edge Resort & Spa

Westbrook Center

Toni and Zak

HK$1,406

HK$1,752 total

includes taxes & fees

4 Oct - 5 Oct

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

19. The Bentley Hotel Southampton

Southampton

Frank

HK$962

HK$1,324 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.

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

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

20. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Renee

HK$794

HK$913 total

includes taxes & fees

30 Oct - 31 Oct

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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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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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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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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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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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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 coastal landscape with a sunset, a marina, and a residential area.

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Although a budget property, staff was helpful and the property is well-maintained. We were pleasantly surprised by the quality of our stay."

Water's Edge Resort & Spa

10/10 Excellent

"Front desk helpful! Indoor bar area nice area for single traveler plenty of space."

The Harbor Front Inn

10/10 Excellent

"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."

Hyatt Place Long Island East End

10/10 Excellent

"Great short weekend trip with me and my wife for a wedding! Great staff! Great little gym, great breakfast. Didn’t use the pools. Walking distance to other bars and restaurants. Would stay here again for sure!"

North Fork Resort

8/10 Good

"We enjoyed our stay. The cabin was clean a few areas of feedback is that the hot water was lackluster. We had many periods of no hot water. The light fixture was very bright in the sitting area. It would’ve been nice if they had a light dimmer so we didn’t have to unscrew the bulbs. One bulb made the room shine. We were impressed that during the storm we received a phone call asking us if we wanted to relocate to another cabin that was not near trees and in the open area. We appreciate that they took the time to extend the offer. We were also impressed that they came around to pick up the fallen branches and used leaf blower to blow off the leaves and sticks on our porch. We would consider reserving in the summer a week to explore the area. Thank you."

Hampton Bays Hotel on Main

10/10 Excellent

"Amazing"

Saybrook Point Resort & Marina

10/10 Excellent

"Absolutely lovely resort, food and the spa is wonderful!"

Hilton Garden Inn Riverhead

8/10 Good

"Good hotel benefited by a good lobby and the delightful Annabel who welcomed us when we arrived after a long journey and managed to arrange food for my family just before the kitchen closed. She looked after us and friends over our stay and made us all very welcome Rooms were spacious though a little dark and we were surprised that given the cost of the hotel room they were only cleaned every other day Facilities are good though and it’s a great base to visit this lovely island. Would happily stay here again"

The Shoals Suites and Slips

10/10 Excellent

"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

HK$613

HK$705 total

1 Oct - 2 Oct

includes taxes & fees

8/10 Very good! (1,016 reviews)

Budget Host East End

30 Lake Avenue Riverhead NY

HK$698

HK$798 total

1 Oct - 2 Oct

includes taxes & fees

6.8/10 (893 reviews)

The Atlantic Hotel

1655 County Road 39 Southampton NY

HK$700

HK$996 total

28 Oct - 29 Oct

includes taxes & fees

Greenview Inn Riverhead

1433 W Main St Riverhead NY

HK$1,017

HK$1,162 total

30 Sept - 1 Oct

includes taxes & fees

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

HK$962

HK$1,324 total

5 Oct - 6 Oct

includes taxes & fees

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

HK$1,659

HK$1,895 total

13 Oct - 14 Oct

includes taxes & fees

Hotels in Southold with star-rating

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 Pier Blue Inn Old Saybrook - Essex and Water's Edge Resort & Spa. See all available top hotels, or vacation rentals in Southold.

What are some of the best holiday rentals that Southold has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This holiday home rental outside of Southold offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all 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?

Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. 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 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.

Southold hotels from HK$622

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Southold

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Southold hotels

1. The Shoals Suites and Slips

2. Sound View Greenport

3. Cliffside Resort Condominiums

4. Silver Sands Motel & Beach Bungalows

5. Zey Hotel

6. The Harbor Front Inn

7. The Menhaden

8. American Beech Hotel

9. The Chequit

10. North Fork Resort

11. Shelter Island House

12. Sag Harbor Inn

13. Oyster Estate

14. House on Chase Creek

15. West Neck Guesthouse

16. Hyatt Place Long Island East End

17. Clinton Motel

18. Water's Edge Resort & Spa

19. The Bentley Hotel Southampton

20. Quality Inn Old Saybrook - Westbrook

Stay near popular Southold attractions

Sparkling Pointe

Croteaux Vineyards

Sannino's Bella Vita Vineyard

Osprey's Dominion

The Old Field Vineyards

Mattebella Vineyards

Horton Point Park

Horton Lane Beach

Learn more about Southold

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Water's Edge Resort & Spa

The Harbor Front Inn

Hyatt Place Long Island East End

North Fork Resort

Hampton Bays Hotel on Main

Saybrook Point Resort & Marina

Hilton Garden Inn Riverhead

The Shoals Suites and Slips

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Budget Host East End

The Atlantic Hotel

Greenview Inn Riverhead

The Bentley Hotel Southampton

The Hampton Maid

Hotels in Southold with star-rating

Frequently asked questions

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