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

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Southold 4 Star Hotels

This weekend
Next weekend

Our top choices for Southold 4-star hotels

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (641 reviews)
"Loved our stay. Our room was gorgeous a s in the perfect location. Would recommend and plan on coming back in the future!"
United States
Tara
The price is Rp9.730.282
Rp12.601.546 total
includes taxes & fees
2 May - 3 May
Sound View Greenport

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (367 reviews)
"Lovely hotel for an off season visit."
United States
Delphine
The price is Rp5.363.263
Rp6.167.821 total
includes taxes & fees
11 May - 12 May
Madison Beach Hotel

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (171 reviews)
"Everything was excellent about this property"
United States
Guy
The price is Rp7.017.030
Rp8.818.631 total
includes taxes & fees
18 May - 19 May
Journey East Hampton

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (157 reviews)
"Bar was excellent "
United States
raje
The price is Rp6.905.821
Rp7.889.900 total
includes taxes & fees
21 May - 22 May
The Maidstone

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (149 reviews)
"Everything and everyone was just lovely! Comfortable Welcoming Great restaurant "
United States
Rachelle
The price is Rp10.837.413
Rp12.442.384 total
includes taxes & fees
18 May - 19 May
Topping Rose House

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (94 reviews)
"Thank you to the crew at The Roundtree for making our stay memorable! This is our second stay, so we couldn't turn down the evening smores by the fire and delivered warm cookies for a late night snack. The grounds and room were so beautiful. We will be back."
United States
Glenn
The price is Rp13.693.654
Rp16.427.315 total
includes taxes & fees
20 May - 21 May
The Roundtree, Amagansett

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 price is Rp5.741.092
Rp7.215.122 total
includes taxes & fees
17 May - 18 May
The Pridwin Hotel

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (152 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (164 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
The price is Rp6.444.571
Rp8.810.138 total
includes taxes & fees
12 May - 13 May
The 1770 House Restaurant & Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (510 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is Rp4.810.797
Rp5.532.417 total
includes taxes & fees
3 May - 4 May
Copper Beech Inn

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
Faraway Sag Harbor

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (26 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
James Pharmacy Bed & Breakfast

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (37 reviews)
"Great hosts"
United States
David
434 on Main

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
Canoe Place Waterfront Residences

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

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)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
East Hampton Art House Bed & Breakfast

PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
PinkWood PlayHouse

Serenity at Shorewood

Serenity at Shorewood
4.0 star property
East Hampton
Serenity at Shorewood
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southold.
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.
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.

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 Rp9.751.779

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.