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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
$1,028 nightly
The price is $1,175
Dec 15 - Dec 16
Total with taxes and fees
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)
"Perfect home and location near the vineyards and restaurants"
United States
Denise R.
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

Find out more about Southold Station

What types of Vacation Homes can I find in Southold Station?

At Expedia, you’ll find great Southold Station Vacation Homes for your family vacation, business trip, romantic weekend break, and more. If you’re planning a vacation with kids, try using the traveler experience filter to select “Family-friendly” Southold Station Vacation Homes. Or, if you’re traveling for work, you can check the “Business-friendly” box to find business-oriented places to stay in Southold Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Southold Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Southold Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Southold Station?

The price per night for Southold Station Vacation Homes in 2026 can start from as low as *. The cost of Vacation Homes varies depending on a number of factors: the dates of your stay, the exact location of the accommodation, and whether there are any special events taking place near Southold Station, to name just three. When there’s a high demand for rooms in Southold Station, this can cause prices to increase, whereas traveling during a quieter time of the year can mean lower prices. Booking through Expedia can help you find some of the best deals for cheap Vacation Homes in Southold Station, so you can sleep easy without going over your budget.

How to find the best deals on Southold Station Vacation Homes?

Expedia’s search function can help you find some of the best deals on Southold Station Vacation Homes. You can select a minimum and maximum price per night according to your budget, and filter by guest ratings and star ratings to ensure you find the right Vacation Homes for your needs. Changing the sort order according to price can also help you to view cheap Vacation Homes in Southold Station at a glance, and you can combine this with our own picks to highlight some of the best available offers. Don’t forget, if you’re an Expedia Rewards member, you can use the “Member Prices” filter to make extra savings on your booking.

Why should I choose Expedia to book Southold Station Vacation Homes?

Booking with Expedia allows you to browse a wide selection of places to stay in Southold Station, complete with search filters that make it easy to locate Vacation Homes that best meet your specific requirements. Our clear and easy-to-use search function makes it effortless to compare amenities, prices, property types, neighborhoods, and much more. At Expedia, you can also find flights, car rental, and activities, and you can combine your bookings for greater savings. Plus, Expedia Rewards members accrue points on all eligible purchases. Build your points total to gain discounts on subsequent bookings in the future. Membership is free, so go ahead and join.

What is the cancellation policy on booking Southold Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Southold Station Vacation Homes with a full refund, depending on the rules and restrictions. For example, some Vacation Homes may not give refunds if you cancel your booking within 24 or 48 hours of your arrival date, and some bookings are non-refundable. Be sure to view the policies provided by the Southold Station Vacation Homes, and confirm the exact cancellation window on your selected location’s details page. If free cancellation is important to you, you can filter for the “Fully refundable” payment type when you search for your Vacation Homes.

*Prices and availability are subject to change. Additional terms may apply 

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