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

Southold Chalets

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Check prices for these dates, December 15 – 16, 2026

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Recommended hotels in Southold

1. The Shoals Suites and Slips

A storefront with a sign reading "THE SHOALS".

2. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

Property grounds

3. The Harbor Front Inn

The entrance to The Harbor Front Inn with a double door and the address number 209.

4. Zey Hotel

A restaurant with a signboard listing its hours of operation.

5. Silver Sands Motel & Beach Bungalows

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

6. Sound View Greenport

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

7. The Chequit

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

8. Oyster Estate

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

9. House on Chase Creek

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

10. Cliffside Resort Condominiums

A balcony with a view of the ocean, a lawn, and a house in the background.

11. The Bentley Hotel Southampton

A white outdoor seating area with a white table and a potted plant.

12. North Fork Resort

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

13. Shorewood Inn

A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

14. Sag Harbor Inn

A building with a brick facade, a porch with steps, an American flag, and a sign with a ship and text.

15. The Menhaden

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

16. American Beech Hotel

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

17. Faraway Sag Harbor

A building with a black front door, a balcony with railings, a street lamp above the door, and a sign that reads 'FARWAY.'

18. The SandPiper

A two-story house with a balcony, a patio with outdoor furniture, and a fenced backyard.

19. Aqua Vista

A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

20. Harbor Heights

A deck with blue and white chairs, a table, and a striped umbrella.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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 white church on a grassy hill, overlooking a sandy beach and the ocean.

Top reviews in Southold

Silver Sands Motel & Beach Bungalows

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

The Shoals Suites and Slips

A storefront with a sign reading "THE SHOALS".

The Harbor Front Inn

The entrance to The Harbor Front Inn with a double door and the address number 209.

Zey Hotel

A restaurant with a signboard listing its hours of operation.

The Chequit

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

House on Chase Creek

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

The Bentley Hotel Southampton

A white outdoor seating area with a white table and a potted plant.

Sound View Greenport

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

The Menhaden

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

Cliffside Resort Condominiums

A balcony with a view of the ocean, a lawn, and a house in the background.

Sag Harbor Inn

A building with a brick facade, a porch with steps, an American flag, and a sign with a ship and text.

American Beech Hotel

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

Faraway Sag Harbor

A building with a black front door, a balcony with railings, a street lamp above the door, and a sign that reads 'FARWAY.'

The Captain Stannard

A large, two-story house with a wrap-around porch, multiple windows, and a chimney.

The Hampton Maid

A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

The Preston House & Hotel

A two-story house with a front porch, a staircase, and a large glass window on the upper floor.

Hyatt Place Long Island East End

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

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