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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
18–23 Sept
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4.89 out of 5 average rating, 197 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
14–21 Jul
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
14–21 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
14–19 Jul
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
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 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
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 92 reviews, 2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
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
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
Home in Westhampton Beach
Westhampton Beach Oasis
New place to stay, 7 bedrooms, 8 beds, 5 bathrooms
14–19 Jul
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Aug
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
14–19 Jul
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
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
Top guest favourite
Home in Southold
Heated Pool, Beautiful 4 bdrm 3 full bath home
4.94 out of 5 average rating, 34 reviews, 4 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
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
14–19 Jul