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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Southold holiday homes

Exterior

Holiday Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3 reviews)
"good experience"
United States
Anonymous traveller
The price is HK$4,678
HK$9,122 total
includes taxes & fees
27 Jan - 28 Jan
Beautifully farmhouse
Smart TV, books

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$792
HK$3,260 total
includes taxes & fees
27 Jan - 28 Jan
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$933
HK$2,852 total
includes taxes & fees
27 Jan - 28 Jan
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV, fireplace, ping pong, books

Holiday Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is HK$32,687
HK$57,682 total
includes taxes & fees
27 Jan - 28 Jan
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Outdoor dining

Holiday Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is HK$772
HK$10,422 total
includes taxes & fees
27 Jan - 28 Jan
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,081
HK$3,927 total
includes taxes & fees
28 Jan - 29 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

Holiday Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is HK$1,170
HK$9,924 total
includes taxes & fees
27 Jan - 28 Jan
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Terrace/patio

Holiday Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$928
HK$1,568 total
includes taxes & fees
27 Jan - 28 Jan
American Beech in Greenport - Petite King Room 7
Property grounds

Holiday Home in Clinton

Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is HK$1,403
HK$2,815 total
includes taxes & fees
27 Jan - 28 Jan
Stylish Modern Stay Steps from the Ocean
Dining

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$1,045
HK$4,042 total
includes taxes & fees
10 Feb - 11 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Fridge, microwave, oven, stovetop

Holiday Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$772
HK$7,625 total
includes taxes & fees
8 Feb - 9 Feb
Blackberry: Private home with jacuzzi year-round
Interior

Holiday Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
The price is HK$35,087
HK$49,030 total
includes taxes & fees
28 Jan - 29 Jan
Sag Harbor Water View w Dock 1.5ml from town
TV, fireplace, stereo, offices

Holiday Home in East Hampton North

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
The price is HK$1,092
HK$4,944 total
includes taxes & fees
1 Feb - 2 Feb
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
Pool

Holiday Home in East Hampton North

Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids
The price is HK$1,092
HK$5,369 total
includes taxes & fees
1 Feb - 2 Feb
Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids
Smart TV, fireplace, books, offices

Holiday Home in Old Saybrook

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is HK$1,949
HK$3,906 total
includes taxes & fees
15 Feb - 16 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Interior

Holiday Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.8 out of 10, Exceptional, (136 reviews)
"We loved our stay!"
United States
Deana L.
The price is HK$1,754
HK$4,263 total
includes taxes & fees
27 Jan - 28 Jan
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Smart TV, fireplace

Holiday Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is HK$1,888
HK$4,268 total
includes taxes & fees
27 Jan - 28 Jan
Renovated Townhouse walk to all
Dining

Holiday Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is HK$2,534
HK$4,891 total
includes taxes & fees
27 Jan - 28 Jan
Immaculate Waterfront 2 bedroom!
On the beach, sun-loungers, beach towels

Holiday Home in Laurel

Beach cottage, private road, private beach, private mooring, private parking.
10.0 out of 10, Exceptional, (1 review)
The price is HK$2,339
HK$6,619 total
includes taxes & fees
16 Feb - 17 Feb
Beach cottage, private road, private beach, private mooring, private parking.
Exterior detail

Holiday Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$2,407
HK$5,182 total
includes taxes & fees
27 Jan - 28 Jan
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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.
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Top Southold Hotel Reviews

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Room was great. Clean and comfortable. Glad I found this place and will be back. "
jason 1-night trip
Posted 4 days ago
The Shoals Suites and Slips

Find out more about Southold

Southold Vacation Homes information

Number of reviews
173
Accommodation
1733 Vacation Homes
Lowest Price
HK$1,568
Highest Price
HK$57,682

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