Photo by Benny Goh

Southold 4 Stars Hotels

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Check availability on Southold 4 Star Hotels

Tonight
Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Southold 4-star hotels

Exterior
Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (343)
"Wonderful staff"
United States
Rebecca
The price is NT$7,721
NT$8,879 total
includes taxes & fees
Feb 5 - Feb 6
Madison Beach Hotel
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (604)
"Nice place"
United States
Mateusz
The price is NT$4,590
NT$6,143 total
includes taxes & fees
Feb 1 - Feb 2
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (60)
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages
View from property
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (161)
"Amazing stay"
United States
Liana
The price is NT$5,809
NT$7,301 total
includes taxes & fees
Jan 18 - Jan 19
Journey East Hampton
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (143)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (92)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is NT$18,715
NT$22,450 total
includes taxes & fees
Jan 11 - Jan 12
The Roundtree, Amagansett
Breakfast and dinner served
Copper Beech Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (506)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is NT$8,785
NT$10,102 total
includes taxes & fees
Jan 13 - Jan 14
Copper Beech Inn
2 restaurants, American cuisine
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is NT$7,431
NT$10,159 total
includes taxes & fees
Jan 8 - Jan 9
The 1770 House Restaurant & Inn
Outdoor pool
Topping Rose House

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (139)
"Our second home :)"
United States
olivia
The price is NT$16,861
NT$19,374 total
includes taxes & fees
Jan 15 - Jan 16
Topping Rose House
Property entrance
The Maidstone

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
The Maidstone
Terrace/patio
The Pridwin Hotel

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel
Aerial view
East Hampton Art House Bed & Breakfast

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)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
East Hampton Art House Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
James Pharmacy Bed & Breakfast
Exterior
The Rams Head Inn

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Private kitchen
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

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

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292)
"Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. "
United States
Katherine
Faraway Sag Harbor
Reception hall
434 on Main

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (36)
"Great hosts"
United States
David
434 on Main
Front of property
The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and Breakfast
Exterior
The Baker House 1650

The Baker House 1650

The Baker House 1650
4.5 star property
East Hampton
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
United States
Marcelle
The Baker House 1650
Front of property
Jedediah Hawkins Inn

Jedediah Hawkins Inn

Jedediah Hawkins Inn
4.0 star property
Jamesport
9.8 out of 10, Exceptional, (18)
"It was our first time in this hotel and the area,it was very relaxing. Great service"
United States
OMAR
Jedediah Hawkins Inn
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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
The price is NT$7,872 per night from Jan 14 to Jan 15
NT$7,872
NT$9,893 total
Jan 14 - Jan 15
includes taxes & fees
8.8/10 Excellent! (76 reviews)
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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
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
"Always an ama"
Priscilla 2-night trip
Posted 3 days ago
Sound View Greenport

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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