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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
2–7 Aug
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4.94 out of 5 average rating, 152 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds
22–27 Aug
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
27 Aug – 1 Sept
New place to stay
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds
3–8 Aug
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds
21–26 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds
26–31 Aug
5.0 out of 5 average rating, 99 reviews
Superhost
Flat in Cutchogue
Cozy North Fork Hideaway
1 bedroom, 1 bed
1–6 Aug
New place to stay
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds
2–7 Aug
New place to stay
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds
2–7 Aug
4.98 out of 5 average rating, 160 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Holiday home in Hampton Bays
Hamptons house -ultra-private backyard, near beach
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4 bedrooms, 4 beds
15–20 Oct
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 46 reviews
Home in East Hampton
The Springs House
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
6–11 Sept
5.0 out of 5 average rating, 95 reviews
Home in East Hampton
East Hamptons 3BR Private +Den Private Entrance
3 bedrooms, 2 queen beds
5–10 Aug
New place to stay