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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Beach house @ NoFo
3 bedrooms, 5 beds, 2 private bathrooms
31 Aug – 6 Sept
,
4.93 out of 5 average rating, 84 reviews
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
4.88 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Aug
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
15–22 Jul
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
16–23 Jul
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 92 reviews, 2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
4.96 out of 5 average rating, 253 reviews, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Jul
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
20–25 Jul
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Aug