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Search results; Over 1,000 homes in Southold

Top guest favourite
Cottage in Southold
Adorable Cottage
2 bedrooms, 4 beds, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 79 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 33 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, 6 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
10–15 Sept
4.96 out of 5 average rating, 178 reviews
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 34 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, 94 reviews
Top guest favourite
Home in East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Greenport
Greenport Village Rental
3 bedrooms, 3 queen beds, 1.5 bathrooms
1–6 Jul
4.99 out of 5 average rating, 113 reviews
Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 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, 68 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 East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 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
13–18 Oct
4.98 out of 5 average rating, 170 reviews
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 147 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 Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in East Lyme
Steps to Black Point Beach • Coastal Home Sleeps 8
4 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.93 out of 5 average rating, 30 reviews