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Search results; Over 1,000 homes in Southold

Top guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
2–7 Aug
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4.95 out of 5 average rating, 146 reviews
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds
14–21 Jul
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds
14–21 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
9–14 Aug
5.0 out of 5 average rating, 92 reviews
Superhost
Home in Sag Harbor
Sag Harbor retreat with pool
3 bedrooms, 4 beds
13–18 Jul
New place to stay
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds
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
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Home in Westhampton Beach
Westhampton Beach Oasis
7 bedrooms, 8 beds
13–18 Jul
New place to stay
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
3 bedrooms, 4 beds
15–20 Jul
4.98 out of 5 average rating, 48 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds
4–9 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed
4–9 Oct
4.97 out of 5 average rating, 180 reviews
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Southold
Heated Pool, Beautiful 4 bdrm 3 full bath home
4 bedrooms, 5 beds
13–18 Jul
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Mattituck
North Fork Getaway Southold Compliant Property
3 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds
7–12 Sept
4.92 out of 5 average rating, 508 reviews
Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 228 reviews
Home in Sag Harbor
Sag Harbor Cottage Perfection
2 bedrooms, 2 queen beds
19–24 Jul
New place to stay