Photo by Benny Goh

Find 4 Star Hotels in Southold, NY from AED 997

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southold 4 Star Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Compare Southold 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is AED 879
AED 1,011 total
includes taxes & fees
1 Jan - 2 January 2026
Madison Beach Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is AED 715
AED 997 total
includes taxes & fees
7 Jan - 8 January 2026
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

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
Exterior
Journey East Hampton

Journey East Hampton

4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (159)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4.0 star property
Greenport
9.8 out of 10, Exceptional, (140)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
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, (91)
"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 AED 2,183
AED 2,619 total
includes taxes & fees
1 Jan - 2 January 2026
The Roundtree, Amagansett
Breakfast and dinner served
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 AED 1,025
AED 1,178 total
includes taxes & fees
9 Dec - 10 Dec
Copper Beech Inn
Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

4.0 star property
East Hampton
9.8 out of 10, Exceptional, (160)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is AED 975
AED 1,333 total
includes taxes & fees
9 Dec - 10 Dec
The 1770 House Restaurant & Inn
Outdoor pool
Topping Rose House

Topping Rose House

4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
The price is AED 1,947
AED 2,237 total
includes taxes & fees
9 Dec - 10 Dec
Topping Rose House
Garden
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 price is AED 1,122
AED 1,282 total
includes taxes & fees
15 Dec - 16 Dec
The Maidstone
Seasonal outdoor pool, pool umbrellas, sun loungers
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

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
The price is AED 1,444
AED 1,649 total
includes taxes & fees
9 Dec - 10 Dec
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

4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (21)
"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
The price is AED 1,054
AED 1,170 total
includes taxes & fees
21 Dec - 22 Dec
James Pharmacy Bed & Breakfast
Exterior
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
Front of property
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is AED 6,463
AED 7,827 total
includes taxes & fees
21 Dec - 22 Dec
Canoe Place Waterfront Residences
Restaurant
Faraway Sag Harbor

Faraway Sag Harbor

4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292)
"staff seemed tired and fed up of people staying!"
United Kingdom
andrew
Faraway Sag Harbor
Reception hall
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
Fridge, microwave, oven, stovetop
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

4.0 star property
Sag Harbor
10.0 out of 10, Exceptional, (11)
"Great house, close to the town, would definitely rent again "
United States
Jared W.
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Interior
Historic House Getaway

Historic House Getaway

4.0 star property
Peconic
9.6 out of 10, Exceptional, (139)
"Great location. Host was was excellent getting any information I need. Clean, nice for our family. Swimming pool and hot tub was nice and clean."
United States
Nathan L.
Historic House Getaway
Living area
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 AED 1,102 per night from Dec 9 to Dec 10
AED 1,102
AED 1,385 total
9 Dec - 10 Dec
includes taxes & fees
9/10 Wonderful! (73 reviews)
Still don't see what you're looking for?
See all properties in Southold.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"The Spa was wonderful and the staff was attentive and helpful. "
Emma 1-night trip
Posted 5 days ago
Madison Beach Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great room with amazing views! Staff was fantastic and the food was great too"
Thomas 1-night trip
Posted 10 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.

  • Search for the lowest price from AED 1,385

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?
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.

Explore a world of travel with Expedia