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

Find 4 Star Hotels in Southold, NY from $224

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Check availability on Southold 4 Star Hotels

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 beach bar with wooden chairs and a small table, overlooking 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
$196 nightly
$224 total
Nov 2 - Nov 3
Total with taxes and fees
Sound View Greenport
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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

2. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
$416 nightly
$475 total
Nov 8 - Nov 9
Total with taxes and fees
Faraway Sag Harbor
A lakeside patio with outdoor seating and a view of the 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.
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.

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
$230 nightly
$262 total
Nov 1 - Nov 2
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
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.

4. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
$257 nightly
$294 total
Oct 20 - Oct 21
Total with taxes and fees
Journey East Hampton
A spacious bedroom with a large bed, a sitting area with a sofa, a chair, and a small ottoman. There are two windows with curtains, a fireplace, and a flat-screen TV mounted on the wall.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
A room with a wicker sofa, a large potted plant, and a window with blinds.
A kitchen with a central island, two wicker chairs, and a bar area with glasses.

5. The Maidstone

The Maidstone
East Hampton
United States
Steven
$287 nightly
$328 total
Oct 25 - Oct 26
Total with taxes and fees
The Maidstone
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 living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

6. Oyster Estate

Oyster Estate
Greenport
United States
Allison
$269 nightly
$307 total
Nov 8 - Nov 9
Total with taxes and fees
Oyster Estate
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
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 beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.
A breakfast buffet with various food items and beverages.

7. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
$428 nightly
$489 total
Oct 21 - Oct 22
Total with taxes and fees
Canoe Place Inn and Cottages
A multi-story hotel with balconies and a beach view.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.
A grand staircase with a chandelier, a reception desk, and a fireplace.
A covered porch with a view of the ocean, a wicker chair, and a small table.

8. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
$289 nightly
$332 total
Nov 1 - Nov 2
Total with taxes and fees
Madison Beach Hotel
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.
Room

9. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Ann
The Pridwin Hotel
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 area with shelves stocked with various bottles and glasses.
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.

10. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
$607 nightly
$698 total
Oct 21 - Oct 22
Total with taxes and fees
Topping Rose House
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 hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.
A large, two-story house with a wrap-around porch and a conservatory.

11. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
$279 nightly
$321 total
Oct 12 - Oct 13
Total with taxes and fees
Copper Beech Inn
A beach with waves gently lapping onto the shore.
A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."
A patio with four wicker chairs arranged around a round table with a fire pit in the center, set in a grassy outdoor area with trees and a fence in the background.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.

12. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Dwight
$624 nightly
$713 total
Nov 1 - Nov 2
Total with taxes and fees
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
A garden pathway leading to a white picket fence and a building with an American flag.
A white house with a sign reading "The 1770 House Restaurant & Inn."
A restaurant with wooden beams, tables with white tablecloths, and a bar area.

13. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
$423 nightly
$550 total
Nov 1 - Nov 2
Total with taxes and fees
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 area with a pool and a wooden deck.
A residential area with houses, a wooden deck, and a garden with pink flowers.
A beach with a lifeguard tower, a few people sitting on chairs, and a white umbrella.

14. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
Clearwater Beach
United States
IVAN
$452 nightly
$517 total
Nov 2 - Nov 3
Total with taxes and fees
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 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 building labeled 'Little House Brewing Co.' with outdoor seating and a porch.
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 dog sitting on a floral-patterned sofa with a wooden coffee table in front.
A wooden staircase with a dog sign, a blue armchair, and a dining area in the background.
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 dining table with a vase of white flowers, surrounded by chairs, in a room with windows and a chandelier.
A barn in a field of wildflowers with a clear sky.
A four-poster bed with white bedding, a wooden dresser with multiple drawers, a nightstand with a lamp, and a window with red curtains.

17. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
Cutchogue
United States
Bent
The Farmhouse Bed and Breakfast
Exterior
Point of interest
Exterior
Bar (on property)

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 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.
An outdoor patio area with tables and chairs, a covered seating area, and a large house in the background.

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 large house with a well-maintained lawn and a wooden gazebo.
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

Mill House Inn

31 North Main Street East Hampton NY
$411 nightly
$470 total
Oct 12 - Oct 13
Total with taxes and fees
Mill House Inn
Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1

112 Northwest Path Sagaponack NY
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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
Horton Point Lighthouse, Southold Long Island New York as seen from above.

Top Southold Hotel Reviews

Find out more about Southold

Southold Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Southold, New York are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Southold 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Southold. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Southold, New York, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Southold hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
To book a 4-star hotel in Southold that matches your budget, use Expedia's handy search filters. Take a look at the availability during your vacation dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly stay first.
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What's the difference between 5-star and 4-star hotels in Southold?
Offering a friendly traveler experience and upscale décor, 4-star hotels are a wonderful option for your Southold escape. These types of stays generally come with loads of useful amenities that make it a breeze to unpack and unwind — think 24-hour room service, pools and restaurants. Or live the high life at a 5-star hotel designed to spoil you with high-end perks and amenities. Full-service health clubs, premium toiletries and gourmet dining are typically included at these deluxe retreats.
Does Southold have any 4-star all-inclusive resorts?
Enjoy a stress-free vacation experience where everything is included in the one rate by using our "All inclusive" filter. Budgeting is a breeze when your accommodations, food and many activities are already taken care of. After something different? Check out the incredible deals on our standard 4-star hotels in and around Southold too.

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