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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.

Two vintage bicycles parked on a grassy lawn in front of a house.

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 beachside outdoor seating area with white Adirondack chairs and a fire pit.

6. Sound View Greenport

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

7. The Chequit

An outdoor patio with wooden tables and wicker chairs, large windows, and ceiling fans.

8. Oyster Estate

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

9. House on Chase Creek

A house on Chase Creek with a porch, steps, and a sign.

10. Cliffside Resort Condominiums

Terrace/patio

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 reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.

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 two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.

16. American Beech Hotel

A white building with a turquoise door, a sign above the door, and a brick step leading to the entrance.

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 covered outdoor patio with a table and chairs, a blue umbrella, and a white fence.

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 beachside outdoor seating area with white Adirondack chairs and a fire pit.

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

An outdoor patio with wooden tables and wicker chairs, large windows, and ceiling fans.

House on Chase Creek

A house on Chase Creek with a porch, steps, and a sign.

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 two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.

Cliffside Resort Condominiums

Terrace/patio

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 white building with a turquoise door, a sign above the door, and a brick step leading to the entrance.

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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