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Our top choices for Southold vacation homes

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3 reviews)
"good experience"
United States
Anonymous traveler
The price is ¥94,914
¥185,794 total
includes taxes & fees
Jan 22 - Jan 23
Beautifully farmhouse

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
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 ¥15,874
¥66,227 total
includes taxes & fees
Jan 26 - Jan 27
Rogers Lake House (87) · CT College+Beach+USCGA

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
East Lyme
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 ¥18,728
¥57,632 total
includes taxes & fees
Jan 22 - Jan 23
The Bay Cottage · Rocky Neck Park, Beach & Niantic

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
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 ¥21,197
¥81,997 total
includes taxes & fees
Feb 10 - Feb 11
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
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 ¥23,665
¥82,463 total
includes taxes & fees
Jan 27 - Jan 28
Beachside Bliss w/ Game Room, Gym & Golf Green

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
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 ¥15,661
¥211,458 total
includes taxes & fees
Jan 22 - Jan 23
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
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 ¥663,164
¥1,170,278 total
includes taxes & fees
Jan 22 - Jan 23
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
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 ¥15,661
¥154,708 total
includes taxes & fees
Feb 8 - Feb 9
Blackberry: Private home with jacuzzi year-round

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
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 ¥28,474
¥57,106 total
includes taxes & fees
Jan 22 - Jan 23
Stylish Modern Stay Steps from the Ocean

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ¥23,729
¥201,338 total
includes taxes & fees
Jan 25 - Jan 26
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is ¥711,855
¥1,007,403 total
includes taxes & fees
Jan 24 - Jan 25
Sag Harbor Water View w Dock 1.5ml from town

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ¥20,407
¥33,801 total
includes taxes & fees
Jan 22 - Jan 23
American Beech in Greenport - Petite King Room 7

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Saybrook Manor
9.6 out of 10, Exceptional, (135 reviews)
"We loved our stay!"
United States
Deana L.
The price is ¥35,593
¥86,016 total
includes taxes & fees
Jan 22 - Jan 23
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons
2.0 star property
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is ¥64,067
¥122,719 total
includes taxes & fees
Jan 22 - Jan 23
4-bedroom beach house minutes from Hamptons

Beach cottage, private road, private beach, private mooring, private parking.

Beach cottage, private road, private beach, private mooring, private parking.
2.5 star property
Laurel
10.0 out of 10, Exceptional, (1 review)
The price is ¥47,457
¥134,286 total
includes taxes & fees
Feb 16 - Feb 17
Beach cottage, private road, private beach, private mooring, private parking.

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
Calverton
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 ¥48,841
¥105,141 total
includes taxes & fees
Jan 22 - Jan 23
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is ¥44,135
¥93,077 total
includes taxes & fees
Jan 25 - Jan 26
Northfork Townhouse walk to all

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is ¥632,760
¥1,001,438 total
includes taxes & fees
Jan 26 - Jan 27
Spacious 5-bedroom house with water views and 2 houses from the bay.

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
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 ¥40,576
¥89,012 total
includes taxes & fees
Jan 22 - Jan 23
Renovated Townhouse walk to all

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is ¥252,313
¥379,898 total
includes taxes & fees
Jan 25 - Jan 26
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
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

Find out more about Southold

Southold Vacation Homes information

Number of reviews
172
Accommodation
1733 Vacation Homes
Lowest Price
¥33,801
Highest Price
¥1,170,278