Holiday houses in Southold
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Top-rated holiday rentals in Southold
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold holiday rentals
Stay near Southold's top sights
Other great holiday rentals in Southold
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
Guest favourite
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Guest favourite
Home in Southold
5.0 out of 5 average rating, 27 reviewsGreenport walk to beach & vineyard! Brand new home
Guest favourite
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Guest favourite
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Guest favourite
Loft in Southold
5.0 out of 5 average rating, 12 reviewsPrivate Apt & Walk to Town/Beach/Train/Wine/Farms
Guest favourite
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Quick stats about holiday 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
$166 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
- Long Island Holiday rentals
- Martha's Vineyard Holiday rentals
- Newark Holiday rentals
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- Rentals with a hot tub Southold
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