Southold Hotel Guide - 4 Stars Hotels in Southold, New York

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Our top choices for Southold 4-star hotels

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (343 reviews)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is Rp4.139.928
Rp4.760.917 total
includes taxes & fees
8 Feb - 9 Feb
Madison Beach Hotel

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 Rp2.262.102
Rp3.066.226 total
includes taxes & fees
19 Jan - 20 Jan
Sound View Greenport

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

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 Rp3.111.502
Rp3.910.405 total
includes taxes & fees
22 Jan - 23 Jan
Journey East Hampton

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

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 Rp10.024.139
Rp12.025.145 total
includes taxes & fees
22 Jan - 23 Jan
The Roundtree, Amagansett

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 Rp4.705.335
Rp5.411.135 total
includes taxes & fees
18 Jan - 19 Jan
Copper Beech Inn

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 Rp4.975.175
Rp6.801.655 total
includes taxes & fees
19 Jan - 20 Jan
The 1770 House Restaurant & Inn

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 Rp9.031.207
Rp10.377.183 total
includes taxes & fees
19 Jan - 20 Jan
Topping Rose House

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 Rp2.996.067
Rp3.423.007 total
includes taxes & fees
19 Jan - 20 Jan
The Maidstone

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

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

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

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

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 Rp21.932.932
Rp26.561.890 total
includes taxes & fees
22 Jan - 23 Jan
Canoe Place Waterfront Residences

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

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

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

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

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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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.

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

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
With Expedia's handy filter tool, bagging a terrific deal on a 4-star hotel in Southold just got easier. Start by keying in your chosen travel dates and length of your break. Then list the results by price and choose a property that best suits your style and budget.

  • Search for the lowest price from Rp5.298.814

What's the difference between 5-star and 4-star hotels in Southold?
If you decide to stay at a 4-star hotel in Southold, you'll typically find loads of conveniences to keep you relaxed, such as a restaurant, pool and gym. You can enjoy excellent service and upmarket surroundings. Choose a 5-star hotel and you'll get a few more perks — think around-the-clock concierge, on-site spas and opulent turndown services. You'll most likely get more amenities and exclusive services at a 5-star stay, though both are fabulous options for luxury guests.
Does Southold have any 4-star all-inclusive resorts?
Finding your dream holiday in Southold is as simple as entering your travel details and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodation, food and activities, or choose a standard 4-star resort in or around this much-loved destination.