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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.94 out of 5 average rating, 149 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–19 Jul
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
12–19 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Guest favourite
Home in Southold
Peconic Pearl Cottage
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 91 reviews, 2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
4.97 out of 5 average rating, 180 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
4.97 out of 5 average rating, 29 reviews, 5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
5.0 out of 5 average rating, 44 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Mattituck
North Fork Getaway Southold Compliant Property
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
4.92 out of 5 average rating, 507 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Southampton
Southampton Dream|Modern 5 beds|Near Watermill
4.91 out of 5 average rating, 102 reviews, 5 bedrooms, 6 beds, 5 bathrooms
13–18 Jul
Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
4.99 out of 5 average rating, 228 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
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
Flat in Sag Harbor
Artists pet friendly apartment and cabin, sauna.
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
4.95 out of 5 average rating, 74 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
Home in Sag Harbor
Sag Harbor Cottage Perfection
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul