Vacation rentals in Southold
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Top-rated vacation rentals in Southold
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Southold vacation rentals
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Other great vacation rentals in Southold
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
May 31 – Jun. 7
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun. 11 – 18
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Feb. 12 – 19
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
Jan. 16 – 23
Home in Southold
5.0 out of 5 average rating, 26 reviewsGreenport walk to beach & vineyard! Brand new home
Jan. 5 – 12
Home in Cutchogue
5.0 out of 5 average rating, 24 reviewsNorth Fork paradise between beaches and vineyards
Jan. 5 – 12
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Sep. 1 – 8
Cottage in Southold
4.89 out of 5 average rating, 19 reviewsQuaint Cottage Close to LI Sound
Jan. 12 – 19
Quick stats about vacation rentals in Southold
Total rentals
220 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$137 CAD before taxes and fees
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