Southold 4 Stars Hotels

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Our top choices for Southold 4-star hotels

Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (620 reviews)
"Nice place"
United States
Mateusz
The price is NT$4,846
NT$6,441 total
includes taxes & fees
Mar 23 - Mar 24
Sound View Greenport
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (347 reviews)
"Staff and hotel are lovely "
United States
Steven
The price is NT$7,035
NT$8,090 total
includes taxes & fees
Mar 31 - Apr 1
Madison Beach Hotel
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (164 reviews)
"Amazing stay"
United States
Liana
The price is NT$5,520
NT$6,938 total
includes taxes & fees
Mar 16 - Mar 17
Journey East Hampton
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (151 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is NT$8,321
NT$9,507 total
includes taxes & fees
Mar 22 - Mar 23
The Maidstone
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (143 reviews)
"Our second home :)"
United States
olivia
The price is NT$16,965
NT$19,494 total
includes taxes & fees
Mar 17 - Mar 18
Topping Rose House
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (147 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows
2 restaurants, American cuisine

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162 reviews)
"Wonderful Inn & staff…The restaurant is also excellent! "
United States
Anthony
The price is NT$8,411
NT$11,499 total
includes taxes & fees
Mar 11 - Mar 12
The 1770 House Restaurant & Inn
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (93 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is NT$18,850
NT$22,613 total
includes taxes & fees
Mar 17 - Mar 18
The Roundtree, Amagansett
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is NT$9,634
NT$10,694 total
includes taxes & fees
Apr 1 - Apr 2
James Pharmacy Bed & Breakfast
Exterior

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (509 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is NT$8,839
NT$10,165 total
includes taxes & fees
Mar 19 - Mar 20
Copper Beech Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
Faraway Sag Harbor
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
Canoe Place Waterfront Residences
Exterior

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18 reviews)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Aerial view

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
East Hampton Art House Bed & Breakfast
Front of property

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (37 reviews)
"Great hosts"
United States
David
434 on Main
Front of property

The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (13 reviews)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and Breakfast
Front of property

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
House, Multiple Beds (Quogue Contemporary) | Pool | Outdoor pool, a heated pool

Quogue Contemporary

Quogue Contemporary
4.0 star property
East Quogue
Quogue Contemporary
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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
Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!"
Gail 3-night trip
Posted 9 days ago
Sound View Greenport
Journey East Hampton

Journey East Hampton

10/10 Excellent
"So cute and cozy! Extremely clean, check in staff was so sweet and attentive. 100% recommend for the price and value ! "
Chantal 2-night trip
Posted 1 month ago
Journey East Hampton

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.

  • Search for the lowest price from NT$6,441

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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