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Search results; Over 1,000 homes in Southold

Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 private baths
Oct 19 – 24
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5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
4.96 out of 5 average rating, 23 reviews
Guest favorite
Guesthouse in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
1 bath
Aug 30 – Sep 4
5.0 out of 5 average rating, 6 reviews
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds, 2 baths
Sep 14 – 19
New place to stay
Top guest favorite
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
Top guest favorite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 baths
Aug 30 – Sep 4
4.95 out of 5 average rating, 55 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 baths
Aug 31 – Sep 6
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 baths
Aug 27 – Sep 1
Home in Waterford
Salty Breeze: Distant Ocean Views & Porch
3 bedrooms, 5 beds, 2 baths
Aug 30 – Sep 4
New place to stay
Guest favorite
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
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bath
Aug 31 – Sep 5
New place to stay
Top guest favorite
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
Top guest favorite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bath
Aug 30 – Sep 4
4.97 out of 5 average rating, 155 reviews
Top guest favorite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 baths
Sep 28 – Oct 3
4.95 out of 5 average rating, 66 reviews
Guest favorite
Home in Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds, 1.5 baths
Aug 31 – Sep 5
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 17 reviews
Guest favorite
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
Top guest favorite
Room in Clinton
Nautical Nook- 1st Floor - Private 1 Bedroom Suite
1 queen bed, 1 bath
Sep 6 – 11
5.0 out of 5 average rating, 111 reviews
Top guest favorite
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