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Vacation Homes in Southold Station

Another rental season is coming up.

10.0 out of 10, Exceptional, (15)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Luxury by the Sea

10.0 out of 10, Exceptional, (8)
"Perfect home and location near the vineyards and restaurants"
Luxury by the Sea

Beautifully farmhouse

10.0 out of 10, Exceptional, (1)
"good experience"
The price is SAR 2,250
SAR 4,405 total
includes taxes & fees
15 Jul - 16 Jul
Beautifully farmhouse

Sea Breeze Paradise: Beachfront & Panoramic Views

10.0 out of 10, Exceptional, (2)
"Everything was perfect, very comfortable and the location was outstanding."
Sea Breeze Paradise: Beachfront & Panoramic Views

Contemporary Colonial home with pristine Peconic bay views, steps to...

10.0 out of 10, Exceptional, (7)
"Everything was spot on, hope to be back!"
Contemporary Colonial home with pristine Peconic bay views, steps to...

Greenport Walk to beach & vineyard from this brand new home

10.0 out of 10, Exceptional, (3)
"This place was perfect for my wife and our friends. We fit three couples comfortably. On our arrival the place was very clean. Lots of towels. We had a wedding in Southold and this place was perfect for us."
Greenport Walk to beach & vineyard from this brand new home

House of Classic Arts and Crafts North Fork

9.8 out of 10, Exceptional, (14)
"It was perfect for what we needed."
House of Classic Arts and Crafts North Fork

Lake House Located Near North Fork Wineries

8.4 out of 10, Very Good, (11)
"good time"
Lake House Located Near North Fork Wineries

Southold Soundfront Private Beach

10.0 out of 10, Exceptional, (22)
"We enjoyed every second of the peace & quiet. Access to the beach couldn't be better. The cottage offers comfortable accommodations both inside and outdoors and the host is just wonderful"
Southold Soundfront Private Beach

Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable

10.0 out of 10, Exceptional, (1)
"Perfect location, close to state parks and beautiful nature. Very well equipped kitchen- high quality cookware and dishes. Cozy, warm - but need to clean the kitchen carpet"
Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable

Country BEACH home!

Country BEACH home!

Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries

9.6 out of 10, Exceptional, (23)
"This property was ideal for us visiting friends in Southold. It's also close to all the vineyards, Greenport and Shelter Island which we visited via ferry en route to Sag Harbour. The property is well equipped for self catering and the deck is lovely overlooking the creek. We had a few issues with the internet on arrival but Jeff kept in touch and sorted the problem. If we visit Southold again we will definitely consider this property as Jeff has plans to update and renovate parts of the...
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries

Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!

9.4 out of 10, Exceptional, (3)
"My only suggestions were may be just do twin beds upstairs with a full bunk beds don’t do well with older kidsAlso brickwork around pool needs some work and front porch was mustyUncomfortable to really utilize the spaceThe kitchen was the bestThank you and good luck"
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!

Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach

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!"
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach

Bayfront Vacation Home in Southold, 5 Bedrooms

10.0 out of 10, Exceptional, (8)
"Great house, great location, access to the water for kayaking and boating. 2nd floor was great living space, deck was perfect with views of bay and the creek. Family had a blast"
Bayfront Vacation Home in Southold, 5 Bedrooms

Steve's Place: Heated Pool, 3BR Southold Home

10.0 out of 10, Exceptional, (5)
"We could not have been more happy with our stay. My wife and I were able to work and vacation here with our 14 and 11 year olds and our 2 year old pup. The property is immaculate and the pool and covered porch is everything. Management was incredibly responsive. And we are 100% looking at calendars for another extended stay next summer."
Steve's Place: Heated Pool, 3BR Southold Home

5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..

9.8 out of 10, Exceptional, (6)
"Swim, bike and spacious luxury home."
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..

Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok

10.0 out of 10, Exceptional, (1)
"Nice stay"
Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok

Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach

9.8 out of 10, Exceptional, (10)
"Home was very cute and spacious. Short drive or 15 min walk to the beaches. Very close to our favorite vineyards (Bedell and Croteaux). House had everything we needed for a great stay in the Northfork. Host was lovely as well and followed up to make sure we had a great stay."
Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach

Luxury north fork estate

2.5 star property
Luxury north fork estate
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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