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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4 bedrooms, 5 beds, 3 private baths
Aug 22–27
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4.9 out of 5 average rating, 84 reviews
Top guest favourite
Home in Greenport
Dream Get Away
2 bedrooms, 2 king beds, 2.5 baths
Aug 23–28
4.94 out of 5 average rating, 291 reviews
Home in Waterford
Salty Breeze: Distant Ocean Views & Porch
3 bedrooms, 5 beds, 2 baths
Aug 30–Sep 4
New place to stay
Guest favourite
Apartment in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bath
Aug 16–21
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 baths
Aug 30–Sep 6
4.94 out of 5 average rating, 34 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 baths
Oct 4–9
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 baths
Aug 14–19
4.93 out of 5 average rating, 86 reviews
Guest favourite
Apartment in Greenport
Lovely 1st floor of farmhouse, wineries/downtown
1 bedroom, 2 beds, 1 bath
Sep 28–Oct 3
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 baths
Aug 26–31
5.0 out of 5 average rating, 101 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 baths
Aug 31–Sep 6
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bath
Oct 4–9
4.97 out of 5 average rating, 195 reviews
Top guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bath
Sep 7–12
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms, 3 beds, 1 bath
Sep 7–12
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 baths
Sep 8–15
5.0 out of 5 average rating, 12 reviews
Guest favourite
Apartment in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 baths
Aug 16–21
4.96 out of 5 average rating, 99 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 baths
Aug 27–Sep 1
Apartment in East Lyme
Charming cottage above beloved Black Point Market
3 bedrooms, 4 beds, 1 bath
Aug 17–22
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bath
Aug 23–28
4.98 out of 5 average rating, 111 reviews
Guest favourite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 bedroom, 1 king bed, 1 bath
Aug 30–Sep 4
4.96 out of 5 average rating, 212 reviews