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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
11–18 Jul
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
11–18 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
10–15 Jul
Top guest favourite
Home in Southold
Best of the North Fork with Heated Pool and Dock
4.97 out of 5 average rating, 33 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
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
Home in Mattituck
North Fork Getaway Southold Compliant Property
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 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
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
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
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
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
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
5.0 out of 5 average rating, 44 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
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
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4.97 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
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
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 3 bathrooms
14–19 Jul
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug