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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

27 Jul – 1 Aug

$2,616 SGD for 5 nights

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4.9 out of 5 average rating, 196 reviews

Top guest favourite

Home in Greenport

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$5,528 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 51 reviews

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$11,264 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 7 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds, 2 bathrooms

11–16 Jul

$9,971 SGD for 5 nights

Top guest favourite

Home in Clinton

The Connecticut Cottage | Historic Modern Charm

2 bedrooms, 2 beds, 2 bathrooms

14–19 Aug

$3,349 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 16 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

6–11 Dec

$3,699 SGD for 5 nights

Home in Orient

Brand new 4 bedrm 4.5 bath home with pool & beach

4 bedrooms, 5 beds, 4.5 bathrooms

7–12 Jul

$14,385 SGD for 5 nights

Guest favourite

Home in Madison

Fabulous pool in beach town!

4 bedrooms, 4 beds, 2.5 bathrooms

10–15 Jul

$5,779 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Top guest favourite

Home in Westbrook

Home Away From Home

3 bedrooms, 6 beds, 2 bathrooms

20–25 Aug

$2,733 SGD for 5 nights

4.99 out of 5 average rating, 83 reviews

Top guest favourite

Room in Sag Harbor

Sag Harbor Home, Perfect for the Solo Traveler

2 beds, 1 bathroom

8–13 Aug

$1,625 SGD for 5 nights

4.96 out of 5 average rating, 248 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

$1,941 SGD for 6 nights

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Free cancellation

4.98 out of 5 average rating, 166 reviews

Top guest favourite

Home in Old Saybrook

Waterfront Oasis 4Bdr/2b

4 bedrooms, 4 beds, 2 bathrooms

11–16 Oct

$3,425 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Guest favourite

Flat in Mattituck

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

2 bedrooms, 2 queen beds, 1 bathroom

5–10 Jul

$3,010 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds, 3 bathrooms

27 Jul – 1 Aug

$9,514 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Cottage in Southampton

10 mins from US OPEN Cottage w heated pool

3 bedrooms, 4 beds, 2 bathrooms

5–10 Jul

$13,335 SGD for 5 nights

4.98 out of 5 average rating, 47 reviews

Top guest favourite

Home in Branford

Adorable Beach House on LI Sound

1 bedroom, 2 beds, 1.5 bathrooms

27 Sept – 2 Oct

$1,588 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 97 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

$11,523 SGD for 7 nights

5.0 out of 5 average rating, 25 reviews

Home in Amagansett

Unit 211: Cottage | Ocean View | Striper

2 bedrooms, 1 bathroom

20–25 Sept

$4,139 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Cottage in East Lyme

Beach Cottage!

2 bedrooms, 2 queen beds, 1 bathroom

13–18 Sept

5.0 out of 5 average rating, 54 reviews