Hotels in Southold, NY - Best Southold Hotels from £67 - 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 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 scene with a wooden structure, two wooden chairs, a campfire, and string lights.

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

1. Sound View Greenport

Greenport

Irene

£176

includes taxes & fees

16 Nov - 17 Nov

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

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

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

A storefront with a sign reading "THE SHOALS".

2. The Shoals Suites and Slips

Southold

Masayo

£179

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

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 child playing with a colorful kite in a grassy field.

3. The Harbor Front Inn

Greenport

Antrii

£176

includes taxes & fees

2 Nov - 3 Nov

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

A restaurant with a signboard listing its hours of operation.

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

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

4. Zey Hotel

Greenport

Renee

£157

includes taxes & fees

20 Oct - 21 Oct

A lakeside patio with outdoor seating and a view of the water.

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

A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

5. Silver Sands Motel & Beach Bungalows

Greenport

Keith

£198

includes taxes & fees

5 Nov - 6 Nov

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

A restaurant with green booths, wooden chairs, and round tables.

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

6. The Pridwin Hotel

Shelter Island Heights

Ann

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 staircase with wooden balusters and a white wall.

A large, white building with multiple windows and a prominent tree in the foreground.

7. The Chequit

The Heights

Patrick

£131

includes taxes & fees

3 Nov - 4 Nov

8. Cliffside Resort Condominiums

Greenport

William

£229

includes taxes & fees

12 Nov - 13 Nov

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

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

9. The Menhaden

Greenport

Daniel

£328

includes taxes & fees

15 Nov - 16 Nov

A wooden pathway leading to a beach with a view of the ocean.

A modern living room with a sofa, a chair, a coffee table, and a view of the sea.

An indoor swimming pool with a view of the beach, lounge chairs, and large windows.

A house with a stone wall and a garden with various plants and flowers.

10. Gurney's Montauk Resort & Seawater Spa

Montauk

Amanda

£365

includes taxes & fees

9 Nov - 10 Nov

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.

11. Water's Edge Resort & Spa

Westbrook Center

Laurie

£166

includes taxes & fees

10 Nov - 11 Nov

A room with a round wooden table, a vase with branches, and a view of a dining area with chairs and a table.

A dining area with a round table, chairs, a vase, and a chandelier.

A living room with a fireplace, a sofa, a coffee table, and a chair.

A rectangular swimming pool with a clear blue water feature, surrounded by a tiled deck.

12. Vine & Sand

Southold

Jennifer

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 spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

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

13. Sag Harbor Inn

Sag Harbor

Terri

£189

includes taxes & fees

1 Nov - 2 Nov

A pool area with umbrellas, potted plants, and a pathway leading to a building.

A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

A spacious living room with a fireplace, comfortable seating, and large windows.

14. Faraway Sag Harbor

Sag Harbor

Thomas

£349

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a covered porch and a chimney.

A dining table with a vase of white flowers, surrounded by chairs, in a room with windows and a chandelier.

A four-poster bed with white bedding, a wooden dresser with multiple drawers, a nightstand with a lamp, and a window with red curtains.

A round table with a white tablecloth, a glass cake stand with a white cake, a glass decanter, wine glasses, and a bouquet of white flowers.

15. The Farmhouse Bed and Breakfast

Cutchogue

Bent

A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

A dining area with a round table, chairs, a vase, and a painting on the wall.

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 modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

16. Oyster Estate

Greenport

Allison

£214

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. American Beech Hotel

Greenport

Mary

£246

includes taxes & fees

18 Oct - 19 Oct

18. Shelter Island House

Shelter Island Heights

Dorothy

£173

includes taxes & fees

18 Oct - 19 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 large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.

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

19. West Neck Guesthouse

Shelter Island Heights

Allie

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

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

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

20. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Celina

£67

includes taxes & fees

19 Oct - 20 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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Custer Institute and Observatory

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

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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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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.

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A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top Southold Hotel Reviews

Hyatt Place Long Island East End

8/10 Good

"Good location. Great breakfast. Very helpful and friendly staff. Be prepared for parking difficulties during wedding season!"

Greenview Inn Riverhead

10/10 Excellent

"Inn is in a rural areas, along scenic country nestled in nature-immersed Riverhead town.Close to Riverheads amazing stores and popular eatery s They offer a more personal, relaxed atmosphere, often featuring a cozy bed rather than a corporate polish.. Great for a short business trip or as a overnite . Unique Inn atmosphere."

The Atlantic Hotel

10/10 Excellent

"This is actually a really great place to stay if you want something reasonable in the Hamptons. The rooms are clean and spacious and the grounds of the hotel are beautiful. I highly recommend!!!"

Hampton Bays Hotel on Main

8/10 Good

"✅ was very good! perfect for 1-2 nights!! Tksss so much"

The Harbor Front Inn

10/10 Excellent

"Beautiful view and quiet"

Zey Hotel

10/10 Excellent

"The staff particularly James were over the top accommodating!!"

Shorewood Inn

10/10 Excellent

"Clean, affordable, helpful staff, good parking. We will stay again when we are in the area."

Sound View Greenport

10/10 Excellent

"The breakfast could have had a better choice."

The Bentley Hotel Southampton

10/10 Excellent

"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

£67

19 Oct - 20 Oct

includes taxes & fees

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