Find 4 Star Hotels in Southold, NY from SAR 1,204

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Southold 4 Star Hotels

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Southold 4-star hotels

Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (649 reviews)
"Clean rooms, great continental breakfast. Was upgraded to waterfront room!!"
United States
Noreen
The price is SAR 1,349
SAR 1,863 total
includes taxes & fees
4 Jun - 5 Jun
Sound View Greenport
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (369 reviews)
"Exceptionally clean and wonderful staff"
United States
Bevin
The price is SAR 1,450
SAR 1,668 total
includes taxes & fees
3 Jun - 4 Jun
Madison Beach Hotel
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (177 reviews)
"Everything was excellent about this property"
United States
Guy
The price is SAR 1,638
SAR 2,059 total
includes taxes & fees
8 Jun - 9 Jun
Journey East Hampton
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (158 reviews)
"Bar was excellent "
United States
raje
The price is SAR 1,482
SAR 1,693 total
includes taxes & fees
31 May - 1 Jun
The Maidstone
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (151 reviews)
"Everything and everyone was just lovely! Comfortable Welcoming Great restaurant "
United States
Rachelle
The price is SAR 1,949
SAR 2,240 total
includes taxes & fees
31 May - 1 Jun
Topping Rose House
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
"Beautiful, calm and serene. What a nostalgic experience. We’re going back next weekend. A perfect weekend getaway from manhattan "
United States
Rita
The price is SAR 1,585
SAR 1,992 total
includes taxes & fees
31 May - 1 Jun
The Pridwin Hotel
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, (64 reviews)
"Peaceful beautiful stay. Wonderful staff. Wonderful restaurant."
United States
Micheal
Canoe Place Inn and Cottages
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, (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 SAR 3,730
SAR 4,474 total
includes taxes & fees
1 Jun - 2 Jun
The Roundtree, Amagansett
Breakfast and dinner served

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (512 reviews)
"Room was decorated very nicely. Spacious and located in the upper building. Staff very friendly and helpful. Andrew our waiter in the restaurant very personable. Offered excellent service. Menu for Valentine's day was special with a wide selection. Food was well prepared and delicious. Breakfast waiter was also very good."
United States
Nelson
The price is SAR 1,047
SAR 1,204 total
includes taxes & fees
31 May - 1 Jun
Copper Beech Inn
Exterior

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
The price is SAR 2,814
SAR 3,537 total
includes taxes & fees
10 Jun - 11 Jun
Faraway Sag Harbor
Outdoor dining

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (166 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 SAR 2,481
SAR 3,392 total
includes taxes & fees
31 May - 1 Jun
The 1770 House Restaurant & Inn
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (153 reviews)
"Lovely lodging"
United States
Timothy
The price is SAR 1,756
SAR 2,006 total
includes taxes & fees
2 Jun - 3 Jun
Silver Sands Motel & Beach Bungalows
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, (26 reviews)
"The fireplace was lovely and the room was cozy and attractive. The bathroom was spacious and clean, however we weren’t able to locate any extra t.p. I would advise people that the staircase going up to the rooms is quite steep. We were able to manage ok, but anyone with difficulty with stairs would have a challenge. The breakfast voucher for breakfast was great and we enjoyed a lovely meal. We also had a wonderful time at The Kate at a Blues concert. Overall, very satisfied with our overnight...
United States
pamela
James Pharmacy Bed & Breakfast
Reception hall

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
Garden

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
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
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)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
East Hampton Art House Bed & 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
Superior Villa, Pool View | Living room

PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
PinkWood PlayHouse
Villa, 3 Bedrooms, Pets Allowed, Pool View | Exterior

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
Sign in
Sign up, it's free

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 SAR 2,345 per night from May 29 to May 30
SAR 2,345
SAR 2,947 total
29 May - 30 May
includes taxes & fees
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.
PoolSpaHot tubBreakfast includedWaterpark
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
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

4/10 Poor
"Room had a gorgeous view and the sauna was great but so over priced"
Meghan 2-night trip
Posted 3 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 SAR 2,947

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.