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Search results; Over 1,000 homes in Southold

Guest favourite

Cottage in Southold

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

3 bedrooms, 4 beds, 2 private bathrooms

15–22 Aug

,

4.92 out of 5 average rating, 66 reviews

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds, 3.5 bathrooms

10–17 Jul

$11,530 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 25 reviews

Home in East Hampton

Tranquil Springs Cottage

2 bedrooms, 2 queen beds, 1 bathroom

23–28 Jul

$4,623 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in East Hampton

Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac

3 bedrooms, 3 beds, 2 bathrooms

10–15 Jul

$12,581 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 18 reviews

Home in Mattituck

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

3 bedrooms, 4 beds, 2 bathrooms

8–13 Sept

$4,683 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$11,271 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 7 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

6–11 Dec

$3,558 SGD for 5 nights

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,823 SGD for 5 nights

Pay $0 today

Free cancellation

4.9 out of 5 average rating, 10 reviews

Top guest favourite

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds, No bathroom

9–14 Aug

$2,300 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 91 reviews

Top guest favourite

Home in Branford

Adorable Beach House on LI Sound

1 bedroom, 2 beds, 1.5 bathrooms

16–21 Aug

$1,784 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 98 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

18–23 Jul

$9,230 SGD for 5 nights

Free cancellation

Top guest favourite

Cottage in Old Saybrook

Luxury Driftwood Cottage @ Saybrook Point

3 bedrooms, 3 beds, 2 bathrooms

26–31 Jul

4.92 out of 5 average rating, 59 reviews

Top guest favourite

Home in Old Saybrook

Waterfront Oasis 4Bdr/2b

4 bedrooms, 4 beds, 2 bathrooms

11–16 Oct

$3,427 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 16 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds, 2 bathrooms

28 Aug – 2 Sept

$12,155 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds, 3 bathrooms

2–7 Aug

$9,520 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in East Hampton

East Hampton Rental w/ Pool, Moments to Amenities

4 bedrooms, 5 beds, 3 bathrooms

1–6 Aug

$9,235 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 82 reviews

Guest favourite

Home in Montauk

Dockside 2BR - Marina - Dining - Charter Access Un

2 bedrooms, 3 beds, 1 bathroom

21–26 Jul

$4,148 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Home in Old Saybrook

Bird Bliss. Our Waterview home &deep water dock.

3 bedrooms, 3 beds, 3 bathrooms

12–17 Jul

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in East Lyme

Walk to the beach at Black Point, Niantic, Ct

3 bedrooms, 4 beds, 2.5 bathrooms

18–24 Sept

$1,942 SGD for 6 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 166 reviews