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Search results; Over 1,000 homes in Southold

Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 254 reviews
Top guest favourite
Guest house in East Hampton
Peaceful cottage
1 bedroom, 1 bed, 1.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 152 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Room in East Hampton
Affordable Suite, own bathroom, close to Montauk
1 double bed, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 112 reviews
Top guest favourite
Home in East Hampton
Bay Access Cottage + Pilates Gym
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 66 reviews
Home in Southold
Sunset Cottage
3 bedrooms, 4 beds, 2.5 bathrooms
23–30 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Greenport
Newly Renovated 2-BR Apartment
2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 90 reviews
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
23–28 Aug
5.0 out of 5 average rating, 93 reviews
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 510 reviews
Top guest favourite
Room in Greenport
Cozy village home
1 double bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 166 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Home in Orient
Orient cottage in the Village
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
4.99 out of 5 average rating, 74 reviews