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Search results; Over 1,000 homes in Southold

Superhost

Home in Southold

Southold waterfront 4 bed, pool open til October

4 bedrooms, 5 beds, 3 private bathrooms

24–29 Jul

$11,038 SGD for 5 nights

,

4.9 out of 5 average rating, 79 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds

24–29 Jul

Free cancellation

Home in Old Lyme

Stoneacre at Point O'Woods

2 bedrooms, 2 queen beds

9–14 Aug

$547 SGD for 5 nights

Free cancellation

Top guest favourite

Flat in Mattituck

Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines

2 bedrooms, 2 queen beds

26–31 Jul

$3,528 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds

3–8 Aug

$7,471 SGD for 5 nights

Free cancellation

New place to stay

Top guest favourite

Cottage in Old Lyme

The Solo Shore Cottage | Walk to Beach + Sun Porch

2 bedrooms, 4 beds

2–7 Aug

$3,391 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Old Saybrook

Red Bird Waterfront Home. Dock available extra!

3 bedrooms, 3 beds

26–31 Jul

$7,381 SGD for 5 nights

4.94 out of 5 average rating, 35 reviews

Superhost

Flat in Mattituck

Vineyard Views: Private Patio and BBQ, Farm Access

1 bedroom, 2 queen beds

19–24 Jul

$2,752 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

18–23 Jul

$11,875 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds

4–9 Oct

$3,822 SGD for 5 nights

4.82 out of 5 average rating, 11 reviews

Home in Amagansett

Unit 211: Cottage | Ocean View | Striper

2 bedrooms

20–25 Sept

$4,140 SGD for 5 nights

Free cancellation

Top guest favourite

Home in Montauk

Dockside 2BR - Marina - Dining - Charter Access Un

2 bedrooms, 3 beds

7–12 Sept

$2,910 SGD for 5 nights

4.96 out of 5 average rating, 28 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds

18–25 Jul

$7,007 SGD for 7 nights

Free cancellation

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds

8–13 Aug

$1,911 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

9–14 Aug

$10,079 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 40 reviews

Top guest favourite

Home in Sag Harbor

Sag Harbor Chic Mid-Century Retreat

3 bedrooms, 4 beds

20–25 Sept

$4,495 SGD for 5 nights

4.99 out of 5 average rating, 77 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds

22–27 Sept

$6,169 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Home in Orient

Newly renovated cottage steps to Jitney and shops

2 bedrooms, 3 beds

19–24 Jul

$4,245 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds

19–26 Jul

$11,525 SGD for 7 nights

5.0 out of 5 average rating, 27 reviews