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Search results; Over 1,000 homes in Southold

Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
14–21 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
14–19 Jul
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
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
15–22 Jul
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
4.98 out of 5 average rating, 166 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
18–24 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
Home in Branford
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 98 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
Home in Westhampton Beach
Westhampton Beach Oasis
New place to stay, 7 bedrooms, 8 beds, 5 bathrooms
26–31 Jul
Top guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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
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 Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
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
Waterfront Oasis 4Bdr/2b
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
11–16 Oct