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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

$2,349 SGD for 5 nights

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4.89 out of 5 average rating, 197 reviews

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds

4–9 Oct

$3,826 SGD for 5 nights

Pay $0 today

Free cancellation

4.9 out of 5 average rating, 10 reviews

Top guest favourite

Home in East Marion

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

3 bedrooms, 3 beds

11–18 Jul

$11,538 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds

6–11 Dec

$3,547 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Home in East Hampton

Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac

3 bedrooms, 3 beds

11–16 Jul

$11,089 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 18 reviews

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds

19–24 Jul

$11,279 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in East Lyme

Walk to the beach at Black Point, Niantic, Ct

3 bedrooms, 4 beds

18–24 Sept

$1,944 SGD for 6 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 166 reviews

Top guest favourite

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds

9–14 Aug

$2,302 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 91 reviews

Guest favourite

Home in Southold

Family and Dog Friendly Private Beach

3 bedrooms, 3 queen beds

25–30 Jul

$5,036 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in East Marion

Waterfront Bungalow w/Private Beach on Peconic Bay

3 bedrooms, 4 beds

1–8 Aug

Free cancellation

4.88 out of 5 average rating, 42 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds

2–7 Aug

$9,526 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds

8–15 Sept

$4,116 SGD for 7 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Old Saybrook

Waterfront Oasis 4Bdr/2b

4 bedrooms, 4 beds

11–16 Oct

$3,430 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 16 reviews

Guest favourite

Home in Madison

Fabulous pool in beach town!

4 bedrooms, 4 beds

19–24 Jul

$5,787 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 22 reviews

Home in Mattituck

3 bed 2 bath sleeps 5 on north fork of Long Island

3 bedrooms, 4 beds

8–13 Sept

$4,687 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds

28 Aug – 2 Sept

$12,163 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds

23–28 Jul

$7,088 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 93 reviews

Home in Cutchogue

Soundwood Retreat. Get away from the noise.

4 bedrooms, 5 beds

31 May – 5 Jun

$6,478 SGD for 5 nights

Free cancellation

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds

12–17 Aug

$1,848 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 28 reviews