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Search results; Over 1,000 homes in Southold

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Guest favourite

Home in Southold

Stylish Beach Getaway: pool & walking location

3 bedrooms, 4 beds, 2 private bathrooms

1–6 Oct

$5,257 SGD for 5 nights

,

4.88 out of 5 average rating, 24 reviews

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Home in East Hampton

East Hamptons Modern 8 Bedroom New Construction

8 bedrooms, 8 beds, 6 bathrooms

1–6 Oct

5.0 out of 5 average rating, 4 reviews

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Guest favourite

Home in Greenport

Greenport Beachfront Home | Private Beach & Sunset

4 bedrooms, 7 beds, 2 bathrooms

4–9 Oct

$5,676 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 9 reviews

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Superhost

Home in Old Saybrook

Beachfront Home with Amazing Views | 5BR Sleeps 11

5 bedrooms, 7 beds, 2 bathrooms

12–17 Oct

$5,301 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Home in East Lyme

Walk to the beach at Black Point, Niantic, Ct

3 bedrooms, 4 beds, 2.5 bathrooms

24–29 Oct

$1,208 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 171 reviews

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Top guest favourite

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 7 beds, 3 bathrooms

6–11 Oct

$5,870 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 15 reviews

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Luxe

Villa in East Hampton

Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess

3 bedrooms, 3 beds, 3.5 bathrooms

1–6 Oct

4.99 out of 5 average rating, 70 reviews

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Guest favourite

Home in Greenport

Walk to Beach or to Town …

3 bedrooms, 4 beds, 2.5 bathrooms

4–9 Oct

$3,048 SGD for 5 nights

4.89 out of 5 average rating, 44 reviews

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Home in Cutchogue

Steps to Beach, Vineyards, Farm Stands & Village

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

5.0 out of 5 average rating, 3 reviews

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Superhost

Home in Old Lyme

Connecticut Beach Home

4 bedrooms, 6 beds, 2 bathrooms

10–15 Oct

New place to stay

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Guest favourite

Home in East Hampton

Chic & Spacious Designer Home, Heated Pool/Spa

3 bedrooms, 4 beds, 2.5 bathrooms

17–22 Oct

$4,191 SGD for 5 nights

4.97 out of 5 average rating, 33 reviews

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Top guest favourite

Home in Montauk

Oceanfront Home Downtown Montauk

3 bedrooms, 6 beds, 1.5 bathrooms

25–30 Oct

4.91 out of 5 average rating, 34 reviews

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Top guest favourite

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

3 bedrooms, 5 beds, 2.5 bathrooms

2–7 Oct

Free cancellation

4.99 out of 5 average rating, 178 reviews

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Guest favourite

Home in Sag Harbor

9 Acre Luxury Compound in Sag Harbor NY

7 bedrooms, 10 beds, 8.5 bathrooms

11–16 Oct

$11,642 SGD for 5 nights

4.99 out of 5 average rating, 148 reviews

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Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

3–8 Oct

$5,909 SGD for 5 nights

4.95 out of 5 average rating, 59 reviews

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Guest favourite

Cottage in Old Saybrook

Charming Old Saybrook Cottage < 1 Mi to Beach

4 bedrooms, 4 beds, 2 bathrooms

27 Oct – 1 Nov

$2,027 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 41 reviews

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Top guest favourite

Home in Greenport

Pennington House

3 bedrooms, 3 beds, 2.5 bathrooms

10–15 Oct

5.0 out of 5 average rating, 35 reviews

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Top guest favourite

Home in East Hampton

Serene East Hampton Escape - Warm Pool til Nov

4 bedrooms, 5 beds, 5.5 bathrooms

12–17 Oct

4.99 out of 5 average rating, 156 reviews

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Guest favourite

Home in East Hampton

The Springs House

4 bedrooms, 5 beds, 2.5 bathrooms

1–6 Oct

5.0 out of 5 average rating, 8 reviews