filters

Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
,
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Room in Greenport
Cozy village home
4.95 out of 5 average rating, 211 reviews, 1 double bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 95 reviews, 2 bedrooms, 3 queen beds, No bathroom
6–11 Sept
Top guest favourite
Room in Westbrook
The Captain James Suite
4.92 out of 5 average rating, 102 reviews, 1 king bed, 1 bathroom
17–22 Aug
Guest favourite
Home in Sag Harbor
5 bedroom luxe home in Sag Harbor w/ heated pool
5.0 out of 5 average rating, 13 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
31 Oct – 5 Nov
Top guest favourite
Flat in Sag Harbor
Artists pet friendly apartment and cabin, sauna.
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Room in East Hampton
Peaceful Suite w/Pool, Hot tub, Private Entry.
5.0 out of 5 average rating, 15 reviews, 1 queen bed, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Old Saybrook
Charming Center of it All Location
4.99 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 73 reviews, 3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
Guest favourite
Rooms in East Hampton
Treetops Room at Ober Oaks in The Hamptons
4.95 out of 5 average rating, 56 reviews, 2 bedrooms, 1 king bed, 1 bathroom
2–7 Aug
Top guest favourite
Room in Greenport
Home on Sterling Harbor, Greenport
4.96 out of 5 average rating, 223 reviews, 1 queen bed, 1 bathroom
23–28 Aug
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
4.99 out of 5 average rating, 76 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Aug
Home in Orient
Orient cottage in the Village
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
Top guest favourite
Guest house in East Hampton
Peaceful cottage
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
23–28 Sept
Home in Greenport
NEW 3BR Coastal Getaway|Walk to Beach|1 Mi to Town
3 bedrooms, 5 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
4.97 out of 5 average rating, 153 reviews, 1 queen bed, 1 bathroom
23–28 Aug