Search Vacation Homes in Southold Station

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Our top choices for Southold Station vacation homes

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

Vacation Home in Southold

Country BEACH home!
10.0 out of 10, Exceptional, (1)
"Very comfortable and clean home! The hosts were very nice and helpful! Would definitely return!"
United States
Megan & Chris D.
Country BEACH home!
10.0 out of 10, Exceptional, (19)
"We spent 3 weeks loving this place! If you want to have a brilliant experience in a relaxing getaway, this is the place for you!"
United States
Shawn V.
Waterfront, private beach, ready for adventure, light & bright!
9.6 out of 10, Exceptional, (24)
"Beautiful property that exceeded expectations. Pros: lovely heated pool, spacious deck, all modern and clean, tastefully decorated, home office if you need to do a bit of work, completely equipped kitchen, comfortable beds, fast wi-fi, powerful & quiet central A/C, located on a quiet street but still 2 miles from excellent dining in Southold, enclosed backyard which is private and beautifully landscaped. A gem!"
United States
Mark D.
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries

Vacation Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
The price is SAR 2,251
SAR 4,407 total
includes taxes & fees
13 Jan - 14 January 2026
Beautifully farmhouse
10.0 out of 10, Exceptional, (11)
"Our family had a wonderful vacation at this property. The house was lovely and accommodated our whole family easily. The host was very helpful and easy to work with."
United States
Susan Z.
Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach
9.8 out of 10, Exceptional, (17)
"This house was just what we were looking for. Great spot close to town in a quiet neighborhood. We would definitely stay here again. "
United States
christopher j.
House of Classic Arts and Crafts North Fork
10.0 out of 10, Exceptional, (6)
"Fantastic stay.. close to all the vineyards.. beautiful cozy home very clean.. great comminication with the host.. will definitely go back again and stay!"
United States
Nelson
Greenport Walk to beach & vineyard from this brand new home
9.8 out of 10, Exceptional, (6)
"Our family of 9 had a great time in the house. The kids loved the playroom, so much to do and the kids bedroom was fun. The house was beautiful, spacious and clean. Bedrooms very comfortable. We enjoyed the pool and the jacuzzi. "
United States
Joan C.
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!

Vacation Home in Southold

Luxury by the Sea
10.0 out of 10, Exceptional, (10)
"In town for a family wedding. Exactly what we were looking for! Beautiful property, convenient, centrally located. Very responsive host."
United States
George B.
Luxury by the Sea
10.0 out of 10, Exceptional, (1)
"Perfect location, ideal vacation house, fully stocked and thoughtfully resourced in the most convenient neighborhood on the North Fork. Town is just minutes away on a a country road with zero traffic. The beach, the house, the ample back yard and the accessibility make this the ideal place to spend your vacation time. Multigenerational appeal with a variety of activities without leaving the house. Avoid the traffic and crowds of Greenport and Shelter Island while still having easy access to...
United States
Kathy D.
Waterfront home with private beach amazing view and sleeps 10 !

Vacation Home in Southold

Southold Soundfront Private Beach
10.0 out of 10, Exceptional, (24)
"Excellent. "
United States
Brian C.
Southold Soundfront Private Beach
2.0 star property
9.8 out of 10, Exceptional, (7)
"Excellent stay!"
United States
Kelli L.
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
10.0 out of 10, Exceptional, (1)
"We wanted to escape the city for a few weeks and absolutely loved staying at Steve’s property! The description of the house was accurate- it was renovated, clean, everything was nearby and convenient. Steve was very responsive and tried to make our stay as pleasurable as possible. We would definitely come back!"
United States
Anna G.
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
9.8 out of 10, Exceptional, (10)
"Great property, well furnished/stocked, clean, terrific location/"
United States
John J P.
Contemporary Colonial home with pristine Peconic bay views, steps to...
10.0 out of 10, Exceptional, (3)
"The whole family loved our stay at this special farm/beach house - a homey blend of a time gone by and modern updates. The views of the vineyard and water and steps to the quiet bay beach were just perfect. Southold and Greenport are a short drive away and there is so much to explore on the North Fork, with wonderful wines right next door at The Old Field Vineyards. Hope to visit again next summer - thank you for sharing!"
United States
TK E.
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
10.0 out of 10, Exceptional, (6)
"What a beautiful vacation in a beautiful spot. Close to Southold and Greenport and our favorite beach. The house and property were immaculate and the pool was such a great amenity to use in lieu of the beach or at the end of the day. Don't want to say too many great things because I want availability for next year😉😉"
United States
Carolyn H.
Steves Place Heated Pool, 3BR Southold Home
8.4 out of 10, Very Good, (11)
"A little house that had all the comforts we needed. Wonderful location and beautiful property. The house was on a pond which created beautiful waterfront views. The owner was very attentive and helpful."
United States
Karen G.
Lake House Located Near North Fork Wineries
10.0 out of 10, Exceptional, (9)
"The home and property are beautiful, serene, and spacious. We have stayed twice already and hope to stay again! This is a very special place and Tony was a great host."
United States
Katie O.
Bayfront Vacation Home in Southold, 5 Bedrooms
9.8 out of 10, Exceptional, (6)
"Swim, bike and spacious luxury home."
United States
Nancy N.
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
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 Station Hotel Reviews