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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
27 Jul – 1 Aug
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4.89 out of 5 average rating, 197 reviews
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
11–18 Jul
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
10–15 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Southold
Best of the North Fork with Heated Pool and Dock
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 63 reviews
Guest favourite
Home in Southold
Peconic Pearl Cottage
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Mattituck
North Fork Getaway Southold Compliant Property
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 179 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, 507 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 199 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 228 reviews