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Search results; Over 1,000 homes in Southold

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Home in Southold

Shelter Bay Cove Waterfront Escape

3 bedrooms, 3 beds, 2 private bathrooms

13–18 Oct

$4,215 SGD for 5 nights

,

4.91 out of 5 average rating, 32 reviews

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Featured hotel

Hotel in Greenport

Oyster Estate, Classic king

1 bedroom, 1 king bed

4–9 Oct

+$307 SGD Airbnb credit

New place to stay

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Top guest favourite

Home in East Hampton

Secluded Luxury: New Gunite Pool, Walk to Bay

5 bedrooms, 5 beds

18–23 Oct

$6,589 SGD for 5 nights

5.0 out of 5 average rating, 58 reviews

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Home in East Hampton

East Hamptons Modern 8 Bedroom New Construction

8 bedrooms, 8 beds

1–6 Oct

$13,794 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

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Luxe

Villa in East Hampton

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

3 bedrooms, 3 beds

9–14 Oct

4.99 out of 5 average rating, 70 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

24–29 Oct

$1,207 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 171 reviews

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Superhost

Home in Old Saybrook

Beachfront Home with Amazing Views | 5BR Sleeps 11

5 bedrooms, 7 beds

12–17 Oct

$4,995 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Greenport

Walk to Beach or to Town …

3 bedrooms, 4 beds

4–9 Oct

$3,046 SGD for 5 nights

4.89 out of 5 average rating, 44 reviews

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Top guest favourite

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 7 beds

6–11 Oct

$5,866 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 15 reviews

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Top guest favourite

Home in Clinton

The Connecticut Cottage | Historic Modern Charm

2 bedrooms, 2 beds

11–16 Oct

$2,224 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 32 reviews

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Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

1–6 Oct

$9,895 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 45 reviews

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Home in Cutchogue

Steps to Beach, Vineyards, Farm Stands & Village

3 bedrooms, 3 beds

1–6 Oct

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds

19–24 Oct

$1,505 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 34 reviews

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Top guest favourite

Home in Old Saybrook

Desirable Fenwood Beach-walk to beach-dogs allowed

3 bedrooms, 3 beds

12–17 Oct

$2,762 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

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Top guest favourite

Home in Greenport

Cozy Farmhouse Retreat in North Fork, NY

3 bedrooms, 3 beds

26–31 Oct

$3,567 SGD for 5 nights

4.92 out of 5 average rating, 136 reviews

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Guest favourite

Home in East Hampton

The Springs House

4 bedrooms, 5 beds

1–6 Oct

5.0 out of 5 average rating, 8 reviews

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Superhost

Home in Old Lyme

Connecticut Beach Home

4 bedrooms, 6 beds

10–15 Oct

New place to stay

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Guest favourite

Villa in Greenport

Greenport Villa with Pool

5 bedrooms, 6 beds

4–9 Oct

$6,669 SGD for 5 nights

4.97 out of 5 average rating, 35 reviews

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Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds

1–6 Oct

4.97 out of 5 average rating, 131 reviews