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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
2 bedrooms, 3 beds, 1 private bathroom
10–15 Oct
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4.89 out of 5 average rating, 90 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds, 3 bathrooms
18–23 Sept
New place to stay
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 reviews
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 57 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Top guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 23 reviews
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Guest favourite
Home in Sag Harbor
Sag Harbor Retreat | Hot Tub & Nature Preserve
4 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 11 reviews