Find 4 Star Hotels in Southold, NY from $317

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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
$304 nightly
The price is $347
May 25 - May 26
Total with taxes and fees
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
$276 nightly
The price is $317
May 11 - May 12
Total with taxes and fees
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
$282 nightly
The price is $322
May 10 - May 11
Total with taxes and fees
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
$401 nightly
The price is $458
May 4 - May 5
Total with taxes and fees
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
$569 nightly
The price is $654
May 17 - May 18
Total with taxes and fees
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
$834 nightly
The price is $953
May 3 - May 4
Total with taxes and fees
The Roundtree, Amagansett

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 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
$355 nightly
The price is $406
May 10 - May 11
Total with taxes and fees
The Pridwin Hotel

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
$392 nightly
The price is $511
May 3 - May 4
Total with taxes and fees
The 1770 House Restaurant & 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

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (509 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
$279 nightly
The price is $321
May 3 - May 4
Total with taxes and fees
Copper Beech Inn

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
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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.

Photo by Benny Goh
Open Photo by Benny Goh

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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 $471

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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