Southold 4 Stars Hotels

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Our top choices for Southold 4-star hotels

Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (343 reviews)
"Wonderful staff"
United States
Rebecca
The price is NT$7,744
NT$8,905 total
includes taxes & fees
Feb 8 - Feb 9
Madison Beach Hotel
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (606 reviews)
"Nice place"
United States
Mateusz
The price is NT$4,236
NT$5,742 total
includes taxes & fees
Jan 27 - Jan 28
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 reviews)
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (162 reviews)
"Amazing stay"
United States
Liana
The price is NT$5,826
NT$7,322 total
includes taxes & fees
Jan 18 - Jan 19
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, (144 reviews)
"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
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (92 reviews)
"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$18,770
NT$22,517 total
includes taxes & fees
Jan 21 - Jan 22
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 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is NT$8,811
NT$10,132 total
includes taxes & fees
Jan 18 - Jan 19
Copper Beech Inn
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)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is NT$9,316
NT$12,736 total
includes taxes & fees
Jan 19 - Jan 20
The 1770 House Restaurant & Inn
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (139 reviews)
"Our second home :)"
United States
olivia
The price is NT$16,911
NT$19,431 total
includes taxes & fees
Jan 19 - Jan 20
Topping Rose House
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is NT$5,610
NT$6,410 total
includes taxes & fees
Jan 19 - Jan 20
The Maidstone
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
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)
"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
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"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
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
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is NT$41,070
NT$49,738 total
includes taxes & fees
Jan 22 - Jan 23
Canoe Place Waterfront Residences
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"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
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (36 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
Exterior

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
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
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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$7,895 per night from Jan 18 to Jan 19
NT$7,895
NT$9,922 total
Jan 18 - Jan 19
includes taxes & fees
8.8/10 Excellent! (77 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
"Amazing room and view from the room was perfect! "
Gregory 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 NT$9,922

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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