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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

$2,347 SGD for 5 nights

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4.89 out of 5 average rating, 197 reviews

Superhost

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

14–21 Jul

$9,139 SGD for 7 nights

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds, 3.5 bathrooms

14–21 Jul

$11,536 SGD for 7 nights

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, 3 bathrooms

13–18 Jul

$12,191 SGD for 5 nights

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, No bathroom

9–14 Aug

$2,302 SGD for 5 nights

5.0 out of 5 average rating, 92 reviews

Top guest favourite

Cottage in Southampton

10 mins from US OPEN Cottage w heated pool

3 bedrooms, 4 beds, 2 bathrooms

15–20 Jul

$14,842 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds, 2 bathrooms

28 Sept – 3 Oct

$4,013 SGD for 5 nights

4.95 out of 5 average rating, 63 reviews

Top guest favourite

Place to stay in Cutchogue

Sunset Suite - walk to vineyards, beaches, & more

1 bedroom, 1 king bed, 1 bathroom

4–9 Oct

$1,501 SGD for 5 nights

4.97 out of 5 average rating, 180 reviews

Top guest favourite

Home in East Marion

POOL + Beach Oasis! Winter deals 2+ nights!

5 bedrooms, 5 beds, 3 bathrooms

4–9 Oct

$6,248 SGD for 5 nights

4.97 out of 5 average rating, 29 reviews

Guest favourite

Home in Southold

Peconic Pearl Cottage

4 bedrooms, 5 beds, 2 bathrooms

7–12 Sept

$4,770 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

3–8 Aug

$5,981 SGD for 5 nights

4.92 out of 5 average rating, 13 reviews

Guest house in Shelter Island

Modern Waterfront Cottage Oasis

1 bedroom, 2 beds, 1 bathroom

18–23 Aug

$7,238 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Mattituck

North Fork Getaway Southold Compliant Property

3 bedrooms, 4 beds, 3 bathrooms

14–19 Jul

$9,677 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Superhost

Home in Sag Harbor

Sag Harbor retreat with pool

3 bedrooms, 4 beds, 1.5 bathrooms

13–18 Jul

$7,951 SGD for 5 nights

New place to stay

Home in Westhampton Beach

Westhampton Beach Oasis

7 bedrooms, 8 beds, 5 bathrooms

13–18 Jul

$20,800 SGD for 5 nights

New place to stay

Home in Sag Harbor

Sag Harbor Cottage Perfection

2 bedrooms, 2 queen beds, 1 bathroom

19–24 Jul

New place to stay

Guest favourite

Villa in Shelter Island

Superb Shelter Island 4 bed Designer with a Pool

3 bedrooms, 4 beds, 3 bathrooms

14–19 Jul

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Southold

Heated Pool, Beautiful 4 bdrm 3 full bath home

4 bedrooms, 5 beds, 3 bathrooms

25–30 Jul

$11,802 SGD for 5 nights

4.94 out of 5 average rating, 34 reviews

Top guest favourite

Flat in Sag Harbor

Updated apartment in historic village home

1 bedroom, 2 beds, 1 bathroom

27 Sept – 2 Oct

$2,515 SGD for 5 nights

4.99 out of 5 average rating, 228 reviews