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Search results; Over 1,000 homes in Southold

Top guest favourite

Guest suite in Southold

Comfortable Suite, a walk to the beach

1 bedroom, 1 bed, 1 private bathroom

5–10 Jul

$1,793 SGD for 5 nights

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4.94 out of 5 average rating, 146 reviews

Top guest favourite

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

3 bedrooms, 5 beds, 2.5 bathrooms

1–7 Jul

5.0 out of 5 average rating, 45 reviews

Top guest favourite

Home in Southold

Private Waterfront home with Dock!

4 bedrooms, 5 beds, 2.5 bathrooms

3–9 Jul

$10,261 SGD for 6 nights

5.0 out of 5 average rating, 18 reviews

Superhost

Home in Southold

Traditional Southold Family Home

4 bedrooms, 5 beds, 2.5 bathrooms

1–6 Jul

New home discount

Guest favourite

Guest house in Southold

Southold- Adorable 1 Bedroom Cottage

1 bedroom, 1 queen bed, 1 bathroom

16–21 Jul

4.9 out of 5 average rating, 80 reviews

Guest favourite

Cottage in Southold

Cozy Cottage on the Great Pond near beach.

2 bedrooms, 3 beds, 1.5 bathrooms

27 Jul – 1 Aug

$2,623 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 195 reviews

Guest favourite

Home in Southold

Peconic Pearl Cottage

4 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,801 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Room in Southold

Cozy guest room - quiet getaway - wine country

1 queen bed, 1 bathroom

27 Oct – 1 Nov

4.96 out of 5 average rating, 150 reviews

Guest favourite

Home in Southold

Southold waterfront 4 bed, pool open til October

4 bedrooms, 5 beds, 3 bathrooms

24–29 Jul

$11,825 SGD for 5 nights

4.9 out of 5 average rating, 77 reviews

Guest favourite

Home in Southold

Le Petit Cottage, Southold, NY

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

$2,190 SGD for 5 nights

4.91 out of 5 average rating, 79 reviews

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

1–8 Jul

$10,401 SGD for 7 nights

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$10,757 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Southold

Country Beach Home!

4 bedrooms, 8 beds, 2.5 bathrooms

30 Aug – 4 Sept

$7,162 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Flat in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

1 bedroom, 1 queen bed, 1 bathroom

5–10 Jul

$3,111 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Flat in Southold

Bright, Southold Studio Apt near beach & town

2 beds, 1 bathroom

12–17 Jul

$2,106 SGD for 5 nights

4.94 out of 5 average rating, 144 reviews

Guest favourite

Home in Southold

East end home away from home

2 bedrooms, 5 beds, 2 bathrooms

5–10 Jul

$3,662 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 20 reviews

Top guest favourite

Cottage in Southold

Adorable Cottage

2 bedrooms, 4 queen beds, 1 bathroom

13–18 Sept

$3,014 SGD for 5 nights

4.95 out of 5 average rating, 75 reviews

Top guest favourite

Home in New Suffolk

Waterfront Beach Cottage

2 bedrooms, 3 beds, 1.5 bathrooms

18–23 Oct

$1,030 SGD for 5 nights

4.96 out of 5 average rating, 69 reviews

Guest favourite

Cottage in Southold

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

3 bedrooms, 4 beds, 2 bathrooms

8–15 Jul

Weekly discount

4.92 out of 5 average rating, 64 reviews