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Our top choices for Town of Southold Town hotels




8.6 out of 10, Excellent, (602)
8.6/10
Excellent
(602)
"Nice place"
"Nice place"Mateusz
The price is €163
€163
includes taxes & fees
14 Jan - 15 Jan




8.8 out of 10, Excellent, (555)
8.8/10
Excellent
(555)
"Room and staff were amazing. "
"Room and staff were amazing. "Manuel
The price is €156
€156
includes taxes & fees
1 Feb - 2 Feb




9.4 out of 10, Exceptional, (232)
9.4/10
Exceptional
(232)
"Great stay, will definitely go again"
"Great stay, will definitely go again"ANTONIO J
The price is €180
€180
includes taxes & fees
4 Jan - 5 Jan




9.8 out of 10, Exceptional, (142)
9.8/10
Exceptional
(142)
"Great get away "
"Great get away "Charles




9.2 out of 10, Wonderful, (292)
9.2/10
Wonderful
(292)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"Susie




9.6 out of 10, Exceptional, (173)
9.6/10
Exceptional
(173)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "Cory
The price is €296
€296
includes taxes & fees
11 Jan - 12 Jan




9.2 out of 10, Wonderful, (10)
9.2/10
Wonderful
(10)
"great place to stay, clean and quiet....loved it"
"great place to stay, clean and quiet....loved it"Darlin




9.2 out of 10, Wonderful, (283)
9.2/10
Wonderful
(283)
"Comfy bed hot shower big room"
"Comfy bed hot shower big room"Kai




8.8 out of 10, Excellent, (195)
8.8/10
Excellent
(195)
"The property was clean beautiful and pleasant.
Loved the trendy decor."
"The property was clean beautiful and pleasant.
Loved the trendy decor."Jennifer
The price is €276
€276
includes taxes & fees
2 Jan - 3 Jan




9.6 out of 10, Exceptional, (13)
9.6/10
Exceptional
(13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."Sandra




9.2 out of 10, Wonderful, (15)
9.2/10
Wonderful
(15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
"Two mid age couples just had a good and relaxing time with great hospitality. "Michail




American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.0 out of 10, Wonderful, (4)
9.0/10
Wonderful
(4)
"We thoroughly enjoyed our stay!"
"We thoroughly enjoyed our stay!"Parent From The Heart, Inc. E.
The price is €260
€260
includes taxes & fees
20 Jan - 21 Jan




Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (23)
10/10
Exceptional
(23)
"Great location and perfect for two couples. We loved staying here."
"Great location and perfect for two couples. We loved staying here."laura d.




The SandPiper
The SandPiperPipes Cove
9.8 out of 10, Exceptional, (30)
9.8/10
Exceptional
(30)
"Property management was great, responsive and helpful recommendations. The property was immaculate and perfectly located for everything from the beach to ferry, restaurants, Main Street and wineries. Plenty of parking on site. Kitchen was well stocked with everything to make a meal or to cook out. Wonderful place!"
"Property management was great, responsive and helpful recommendations. The property was immaculate and perfectly located for everything from the beach to ferry, restaurants, Main Street and wineries. Plenty of parking on site. Kitchen was well stocked with everything to make a meal or to cook out. Wonderful place!"Laurie G.




Harbor Heights
Harbor HeightsPipes Cove
9.8 out of 10, Exceptional, (14)
9.8/10
Exceptional
(14)
"This was a perfect location and such a cute place! The apartment was spotless and well appointed. "
"This was a perfect location and such a cute place! The apartment was spotless and well appointed. "Pamela




Beautifully farmhouse
Beautifully farmhouseSouthold
10.0 out of 10, Exceptional, (3)
10/10
Exceptional
(3)
"good experience"
"good experience"Anonymous traveller
The price is €1,367
€1,367
includes taxes & fees
1 Feb - 2 Feb




Surrounded by nature, come stay in this 1 bedroom private, serene location
Surrounded by nature, come stay in this 1 bedroom private, serene locationSouthold
10.0 out of 10, Exceptional, (3)
10/10
Exceptional
(3)
"We enjoyed our stay here. Great host, easy check in. Clean, comfortable and centrally located. Would definitely stay again. "
"We enjoyed our stay here. Great host, easy check in. Clean, comfortable and centrally located. Would definitely stay again. "Cheryl H.




American Beech in Greenport NY - King Suite 1
American Beech in Greenport NY - King Suite 1Greenport
10.0 out of 10, Exceptional, (5)
10/10
Exceptional
(5)
"Perfect
Great place"
"Perfect
Great place"Dean J.
The price is €297
€297
includes taxes & fees
4 Jan - 5 Jan




9.8 out of 10, Exceptional, (22)
9.8/10
Exceptional
(22)
"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."
"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."Amy




9.2 out of 10, Wonderful, (12)
9.2/10
Wonderful
(12)
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "Andrea
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.
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.
Showing deals for:9 Jan - 11 Jan
Image gallery for Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Cutchogue
10/10Exceptional (28 reviews)
6% off
Price is €797
€797
for 2 nights, 1 cottage
€399 per night
includes taxes & fees
Image gallery for Arbor View House B&B

Arbor View House B&B
3.5 star property
East Marion
9.2/10Wonderful (15 reviews)
10% off
Price is €737
€737
for 2 nights, 1 room
€369 per night
includes taxes & fees
Image gallery for Lovely Cottage in the Heart of Long Island Wine country

Lovely Cottage in the Heart of Long Island Wine country
Southold
9.8/10Exceptional (30 reviews)
6% off
Price is €492
€492
for 2 nights, 1 cottage
€246 per night
includes taxes & fees
Image gallery for Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country
Peconic
10/10Exceptional (184 reviews)
6% off
Price is €1,060
€1,060
for 2 nights, 1 cottage
€530 per night
includes taxes & fees
Image gallery for Greenport Walk to beach & vineyard from this brand new home

Greenport Walk to beach & vineyard from this brand new home
Southold
10/10Exceptional (6 reviews)
7% off
Price is €2,096
€2,096
for 2 nights, 1 home
€1,048 per night
includes taxes & fees
Image gallery for Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Orient
9.4/10Exceptional (10 reviews)
7% off
Price is €3,588
€3,588
for 2 nights, 1 home
€1,794 per night
includes taxes & fees
Image gallery for Historic House Getaway

Historic House Getaway
4.0 star property
Peconic
9.6/10Exceptional (139 reviews)
6% off
Price is €1,776
€1,776
for 2 nights, 1 home
€888 per night
includes taxes & fees
Image gallery for Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!

Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Greenport
10/10Exceptional (26 reviews)
7% off
Price is €1,458
€1,458
for 2 nights, 1 home
€729 per night
includes taxes & fees
Image gallery for Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork

Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
Mattituck
10/10Exceptional (17 reviews)
13% off
Price is €895
€895
for 2 nights, 1 room
€448 per night
includes taxes & fees
Image gallery for Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6/10Excellent (602 reviews)
9% off
Price is €450
€450
for 2 nights, 1 room
€225 per night
includes taxes & fees
Image gallery for Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2/10Wonderful (292 reviews)
10% off
Price is €630
€630
for 2 nights, 1 room
€315 per night
includes taxes & fees
Image gallery for NEW VICTORIAN GEM IN GREENPORT

NEW VICTORIAN GEM IN GREENPORT
Greenport
10/10Exceptional (11 reviews)
6% off
Price is €2,360
€2,360
for 2 nights, 1 home
€1,180 per night
includes taxes & fees
Image gallery for Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Southold
10/10Exceptional (181 reviews)
7% off
Price is €2,392
€2,392
for 2 nights, 1 home
€1,196 per night
includes taxes & fees
Image gallery for Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8/10Exceptional (142 reviews)
10% off
Price is €639
€639
for 2 nights, 1 room
€320 per night
includes taxes & fees
Image gallery for Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Greenport,
10/10Exceptional (21 reviews)
6% off
Price is €755
€755







