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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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Southold vacation rentals
Stay near Southold's top sights
Other great vacation rentals in Southold
Guest favourite
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Jun. 3 – 10
$655 CAD per night
Guest favourite
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun. 11 – 18
$1,056 CAD per night
Guest favourite
Home in Southold
4.96 out of 5 average rating, 26 reviewsBright Oasis in Beautiful North Fork Wine Country
Oct. 11 – 18
$1,080 CAD per night
Guest favourite
Home in Southold
5.0 out of 5 average rating, 25 reviewsGreenport walk to beach & vineyard! Brand new home
Nov. 5 – 12
$969 CAD per night
Guest favourite
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Jul. 14 – 21
$1,033 CAD per night
Superhost
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Aug. 2 – 9
$1,331 CAD per night
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
Oct. 19 – 26
$1,438 CAD per night
Guest favourite
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Oct. 24 – 31
$845 CAD per night
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
$138 CAD before taxes and fees
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