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

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Check availability on Southold 4 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Southold 4-star hotels

A spacious room with wicker furniture, large windows, and a view of the sea.

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
$183 nightly
The price is $209
Nov 23 - Nov 24
Total with taxes and fees
Sound View Greenport
A pool area with umbrellas, potted plants, and a pathway leading to a building.

2. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
$351 nightly
The price is $402
Nov 16 - Nov 17
Total with taxes and fees
Faraway Sag Harbor
A beachside outdoor seating area with white Adirondack chairs and a fire pit.

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (186 reviews)
"Nicely renovated and enjoyable."
United States
Becky
$232 nightly
The price is $266
Nov 1 - Nov 2
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
A cozy interior with a bar area, seating, and a fireplace.

4. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (300 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
$219 nightly
The price is $250
Nov 29 - Nov 30
Total with taxes and fees
Oyster Estate
A row of modern, two-story buildings with balconies, surrounded by dense greenery.

5. Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (210 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
$252 nightly
The price is $288
Nov 8 - Nov 9
Total with taxes and fees
Journey East Hampton
A multi-story hotel with balconies and a beach view.

6. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.6 out of 10, Exceptional, (396 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
$271 nightly
The price is $312
Nov 5 - Nov 6
Total with taxes and fees
Madison Beach Hotel
A dining area with a table set for two, a wine bottle, and two wine glasses. There are wicker chairs, a bookshelf with various bottles, and a chandelier.

7. The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very good, (180 reviews)
"Great staff and amenities like restaurant"
United States
Steven
$212 nightly
The price is $242
Nov 5 - Nov 6
Total with taxes and fees
The Maidstone
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

8. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (76 reviews)
"We loved everything about this hotel… from the premises, decor, quality of food, respectful but friendly staff etc…Bravo!"
Canada
Corrado
$515 nightly
The price is $588
Nov 28 - Nov 29
Total with taxes and fees
Canoe Place Inn and Cottages
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

9. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (164 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
$607 nightly
The price is $698
Nov 20 - Nov 21
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.

10. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (530 reviews)
"Nice stay. Quite,"
United States
Joseph
$279 nightly
The price is $321
Nov 1 - Nov 2
Total with taxes and fees
Copper Beech Inn
A round outdoor table with a fire pit, two glass jars with grains, and a black grill.

11. The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
9.8 out of 10, Exceptional, (101 reviews)
"Absolutely awesome place. Professional staff were extremely helpful. Pet and family friendly."
United States
Dwight
$619 nightly
The price is $707
Nov 17 - Nov 18
Total with taxes and fees
The Roundtree, Amagansett
A living room with a fireplace, a television mounted above it, and a dining area in the background.

12. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (172 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
$356 nightly
The price is $464
Nov 30 - Dec 1
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.

13. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65 reviews)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
$452 nightly
The price is $517
Nov 2 - Nov 3
Total with taxes and fees
East Hampton Art House Bed & Breakfast
A lakeside property with a dock, a large building, and surrounding greenery.

14. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (128 reviews)
"Wonderful- so charming and comfortable; upscale yet casual"
United States
Ann
The Pridwin Hotel
A bedroom with a four-poster bed, white bedding, and a vase of white flowers on the nightstand.

15. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (26 reviews)
"Great location for an overnight stay"
United States
Diane
James Pharmacy Bed & Breakfast
A two-story house with a front porch, a chimney, and a sign reading "Main Entrance."

16. 434 on Main

434 on Main
4.0 star property
Amagansett
10.0 out of 10, Exceptional, (38 reviews)
"Great hosts"
United States
David
434 on Main
A two-story house with a covered porch and a chimney.

17. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (16 reviews)
"The place is lovely. We loved the garden the house the host th alpacas and the beach parking pass. It is really expensive to stay in that area but the place is great"
United States
Bent
The Farmhouse Bed and Breakfast
Exterior

18. The Baker House 1650

The Baker House 1650
4.5 star property
East Hampton
9.4 out of 10, Exceptional, (33 reviews)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
United States
Marcelle
The Baker House 1650
A large, two-story house with a well-maintained lawn and a pergola with vines.

19. Jedediah Hawkins Inn

Jedediah Hawkins Inn
4.0 star property
Jamesport
9.8 out of 10, Exceptional, (18 reviews)
"It was our first time in this hotel and the area,it was very relaxing. Great service"
United States
OMAR
Jedediah Hawkins Inn
A living room with a white sofa, a glass coffee table with two blue vases, a dining area with a wooden table and chairs, and a large mirror on the wall.

20. The Mainstay

The Mainstay
4.0 star property
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
The price is $470 total per night from Nov 1 to Nov 2
$470 total
Nov 1 - Nov 2
Total with taxes and fees
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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 coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top Southold Hotel Reviews

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Perfect experience all around. But very noisy at 8 am - maintenance trucks, etc too loud. Would be better if they started at 9 am. A little jarring to hear the noise right outside rooms so early"
Mary Ann 1-night trip
Posted less than an hour ago
Faraway Sag Harbor

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.

  • Search for the lowest price from $470

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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