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

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

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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 Rp7.233.300
Rp9.794.469 total
includes taxes & fees
28 Jun - 29 Jun
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 Rp9.248.313
Rp11.622.796 total
includes taxes & fees
22 Jun - 23 Jun
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 Rp8.059.861
Rp9.268.841 total
includes taxes & fees
21 Jun - 22 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, (181 reviews)
"Lovely hotel, great facilities and very welcoming staff. Thoroughly recommend."
United Kingdom
Dan
The price is Rp11.653.650
Rp14.645.758 total
includes taxes & fees
6 Jul - 7 Jul
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 Rp17.601.030
Rp20.171.686 total
includes taxes & fees
22 Jun - 23 Jun
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 Rp9.912.300
Rp11.890.965 total
includes taxes & fees
22 Jun - 23 Jun
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 Rp12.769.900
Rp15.464.929 total
includes taxes & fees
23 Jun - 24 Jun
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 Rp4.982.940
Rp5.730.381 total
includes taxes & fees
17 Jun - 18 Jun
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 Rp26.672.931
Rp31.997.460 total
includes taxes & fees
29 Jun - 30 Jun
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 Rp12.502.000
Rp14.283.535 total
includes taxes & fees
17 Jun - 18 Jun
Silver Sands Motel & Beach Bungalows
Seasonal outdoor pool, 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 Rp15.448.900
Rp19.415.474 total
includes taxes & fees
22 Jun - 23 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, (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 Rp10.782.975
Rp14.740.930 total
includes taxes & fees
28 Jun - 29 Jun
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 Rp14.198.700 per night from 29 Jun to 30 Jun
Rp14.198.700
Rp17.844.283 total
29 Jun - 30 Jun
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 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 Rp17.844.283

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.