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

Southold 4 Stars Hotels

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Check availability on Southold 4 Star Hotels

Tonight
Sep 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Southold 4-star hotels

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

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$8,406
NT$10,508 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

2. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$14,667
NT$18,433 total
includes taxes & fees
Oct 4 - Oct 5
Faraway Sag Harbor
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

3. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$8,742
NT$10,986 total
includes taxes & fees
Oct 12 - Oct 13
Journey East Hampton
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.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

4. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
NT$19,123
NT$24,032 total
includes taxes & fees
Sep 16 - Sep 17
The Pridwin Hotel

5. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,655
NT$10,383 total
includes taxes & fees
Oct 13 - Oct 14
The Maidstone
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
A cozy room with a large window, a sofa, a small table with a tray, and a pair of slippers on the floor.
A person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.
A breakfast buffet with various food items and beverages.

6. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
NT$15,031
NT$18,203 total
includes taxes & fees
Oct 5 - Oct 6
Canoe Place Inn and Cottages
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 beach with sun loungers and umbrellas, a sandy path, and a view of the water.

7. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
NT$10,284
NT$11,750 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
A multi-story hotel with balconies and a beach view.
A covered porch with a view of the ocean, a wicker chair, and a small table.
A coastal hotel with a pier, beach, and boats.
A grand staircase with a chandelier, a reception desk, and a fireplace.

8. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$14,246
NT$16,382 total
includes taxes & fees
Sep 21 - Sep 22
Madison Beach Hotel
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.

9. Oyster Estate

Oyster Estate
Greenport
United States
Matthew
NT$10,886
NT$13,715 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A large, two-story house with a wrap-around porch and a conservatory.
A spacious room with a large bed, a staircase, and a door leading to another room.

10. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,829
NT$10,153 total
includes taxes & fees
Sep 16 - Sep 17
Copper Beech Inn
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A modern hotel room with a bed, bedside table, and a view of the garden.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A bar area with shelves stocked with various bottles and glasses.

11. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$31,185
NT$35,740 total
includes taxes & fees
Sep 16 - Sep 17
Topping Rose House
A beach with waves gently lapping onto the shore.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.
A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."
A modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

12. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
NT$21,970
NT$26,355 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
A white house with a sign reading "The 1770 House Restaurant & Inn."
A garden pathway leading to a white picket fence and a building with an American flag.
A living room with a fireplace, a television mounted above it, and a dining area in the background.

13. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$15,466
NT$21,143 total
includes taxes & fees
Sep 21 - Sep 22
The 1770 House Restaurant & Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.
A sliding glass door leading to an outdoor deck with a view of a swimming pool and greenery.
A large, modern house with a swimming pool, surrounded by lush greenery and trees.
A residential area with houses, a wooden deck, and a garden with pink flowers.

14. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
Clearwater Beach
United States
IVAN
NT$21,667
NT$24,755 total
includes taxes & fees
Sep 28 - Sep 29
East Hampton Art House Bed & Breakfast
A four-poster bed with a green area rug, a white armchair, a television mounted on the wall, and a chandelier.
A building labeled 'Little House Brewing Co.' with outdoor seating and a porch.
A modern living room with a white sofa, a flat-screen TV mounted on the wall, a small console table with decorative items, and a patterned rug.
A room with a fireplace, a television mounted above it, and a round table with a bowl and a book.

15. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
Old Saybrook Center
United States
Diane
James Pharmacy Bed & Breakfast
A vase with orange flowers on a table.
A wooden staircase with a dog sign, a blue armchair, and a dining area in the background.
A dog sitting on a floral-patterned sofa with a wooden coffee table in front.
A two-story house with a front porch, a chimney, and a sign reading "Main Entrance."

16. 434 on Main

434 on Main
Amagansett North
United States
David
434 on Main
A two-story house with a covered porch and a chimney.
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.
A barn in a field of wildflowers with a clear sky.
A dining table with a vase of white flowers, surrounded by chairs, in a room with windows and a chandelier.

17. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
Cutchogue
United States
Bent
The Farmhouse Bed and Breakfast

18. The Baker House 1650

The Baker House 1650
East Hampton
United States
Marcelle
The Baker House 1650
A brick pathway leading to a large, two-story building with a symmetrical facade, surrounded by manicured hedges and trees.
A cozy living room with a fireplace, a bar area with bottles, and a painting on the wall.
A gazebo with a dome roof, surrounded by a garden with various flowers and a pathway leading to it.
A restaurant with a long table set for a meal, surrounded by chairs, and a wine rack with bottles.

19. Jedediah Hawkins Inn

Jedediah Hawkins Inn
Jamesport
United States
OMAR
Jedediah Hawkins Inn
A modern kitchen with a central island, bar stools, stainless steel appliances, and wooden flooring.
A patio with a fire pit, outdoor furniture, and a pool.
A long dining table set for a meal with chairs, a chandelier, and a large abstract painting on the wall.
A living room with a fireplace, two armchairs, a hanging light fixture, and a large window.

20. The Mainstay

The Mainstay
Southampton
The Mainstay
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southold.
Mill House Inn

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31 North Main Street East Hampton NY
NT$27,689
NT$40,017 total
Sep 15 - Sep 16
includes taxes & fees
Mill House Inn
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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.

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.
Photo by Benny Goh

Top Southold Hotel Reviews

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 1 day ago
Faraway Sag Harbor

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
With Expedia's sort and search filters, bagging a great deal on a 4-star hotel in Southold just got simpler. Start by keying in your chosen arrival date and length of your escape. Then list the results by price and choose a hotel that best suits your style and budget.
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What's the difference between 5-star and 4-star hotels in Southold?
If you choose to book a stay at a 4-star hotel in Southold, you'll usually find loads of amenities to make sure you're comfortable, such as a restaurant, gym and pool. You can enjoy excellent service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few extra bells and whistles — think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get extra amenities and first-rate services at a 5-star retreat, though both are fabulous options for luxury guests.
Does Southold have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next escape in Southold where just about everything is taken care of, from your meals to your room, activities and entertainment. We can also help you find standard 4-star stays in and around this much-loved destination.

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