Photo by Benny Goh

Find 4 Star Hotels in Southold, NY from $231

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

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
$244 nightly
The price is $280
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$237 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
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
$444 nightly
The price is $507
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$223 nightly
The price is $255
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
$203 nightly
The price is $231
Dec 21 - Dec 22
Total with taxes and fees
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
$624 nightly
The price is $713
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$279 nightly
The price is $321
Dec 8 - Dec 9
Total with taxes and fees
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
$279 nightly
The price is $363
Dec 8 - Dec 9
Total with taxes and fees
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
$559 nightly
The price is $643
Dec 8 - Dec 9
Total with taxes and fees
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
$275 nightly
The price is $315
Jan 6 - Jan 7, 2026
Total with taxes and fees
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
$437 nightly
The price is $499
Dec 8 - Dec 9
Total with taxes and fees
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
$302 nightly
The price is $335
Dec 21 - Dec 22
Total with taxes and fees
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
$395 nightly
The price is $451
Jan 1 - Jan 2, 2026
Total with taxes and fees
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)
$1,819 nightly
The price is $2,079
Dec 21 - Dec 22
Total with taxes and fees
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
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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
$330 nightly
The price is $377 total per night from Dec 8 to Dec 9
$377 total
Dec 8 - Dec 9
Total with taxes and fees
9/10 Wonderful! (73 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

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 9 days ago
Sound View Greenport

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 $377

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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