Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

Southold 4 Stars Hotels

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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, (655 reviews)
"Love being on the water"
United States
Gina
The price is NT$13,072
NT$17,645 total
includes taxes & fees
Jun 29 - Jun 30
Sound View Greenport
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (87 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 NT$17,375
NT$21,836 total
includes taxes & fees
Jun 16 - Jun 17
The Pridwin Hotel
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (371 reviews)
"Exceptionally clean and wonderful staff"
United States
Bevin
The price is NT$15,537
NT$17,868 total
includes taxes & fees
Jun 29 - Jun 30
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, (181 reviews)
"Lovely hotel, great facilities and very welcoming staff. Thoroughly recommend."
United Kingdom
Dan
The price is NT$20,640
NT$25,939 total
includes taxes & fees
Jul 6 - Jul 7
Journey East Hampton
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (152 reviews)
"Amazing"
United Kingdom
Ming Da
The price is NT$31,173
NT$35,726 total
includes taxes & fees
Jun 21 - Jun 22
Topping Rose House
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (160 reviews)
"It was very fantastic and the staff was very helpful. Late last night, my companion had need of feminine products and the staff was able to assist by giving her own. She was a lifesaver."
United States
Min
The price is NT$19,770
NT$23,716 total
includes taxes & fees
Jun 21 - Jun 22
The Maidstone
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
The price is NT$22,617
NT$27,390 total
includes taxes & fees
Jun 23 - Jun 24
Canoe Place Inn and Cottages
Breakfast and dinner served

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (514 reviews)
"It could use an upgrade for the Breakfast menu."
United States
EUGENE
The price is NT$8,825
NT$10,149 total
includes taxes & fees
Jun 16 - Jun 17
Copper Beech Inn
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, (95 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is NT$47,241
NT$56,671 total
includes taxes & fees
Jun 29 - Jun 30
The Roundtree, Amagansett
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (154 reviews)
"Lovely lodging"
United States
Timothy
The price is NT$16,449
NT$18,793 total
includes taxes & fees
Jun 16 - Jun 17
Silver Sands Motel & Beach Bungalows
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

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 NT$25,147
NT$31,604 total
includes taxes & fees
Jun 16 - Jun 17
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, (167 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 NT$19,098
NT$26,108 total
includes taxes & fees
Jun 29 - Jun 30
The 1770 House Restaurant & Inn
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
Villa, 3 Bedrooms, Pets Allowed, Pool View | Exterior

Serenity at Shorewood

Serenity at Shorewood
4.0 star property
East Hampton
Serenity at Shorewood
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
Superior Villa, Pool View | Living room

PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
PinkWood PlayHouse
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
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
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$25,147 per night from Jun 16 to Jun 17
NT$25,147
NT$31,604 total
Jun 16 - Jun 17
includes taxes & fees
9/10 Wonderful! (85 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
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"We had an absolutely enchanting long weekend at the Pridwin. This beautifully appointed property exudes timeless elegance, with thoughtful touches that made us feel truly pampered from the moment the staff reached out to us long before our stay. The complimentary breakfast, in-room snacks and drinks, outdoor fire pits with rocking chairs, and cozy nights spent by the fireplace with bar service turned our visit into a heartfelt home away from home — far warmer and more inviting than any sterile hotel experience. The outdoor heated pool was simply divine, backed by attentive and friendly service that made every swim a pleasure. Shelter Island offers the perfect backdrop for adventure and relaxation — exploring nearby vineyards to the north, or heading south by ferry to Sag Harbor and the broader Hamptons — all while knowing you can retreat each evening to this quiet, serene haven. A special shoutout to Tony, the bartender, whose genuine warmth and friendliness made us feel so welcome every time we crossed paths. Not to mention, he crafts exquisite cocktails and martinis that truly elevated our evenings."
Jasmin 4-night trip
Posted 8 days ago
The Pridwin Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great"
priscilla 1-night trip
Posted 2 weeks 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.

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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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