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Search results; Over 1,000 homes in Orient

Flat in Orient
Suite 5: 2 Bedroom, 1 Bath
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.56 out of 5 average rating, 18 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Home in Greenport
3BR Greenport Getaway |Walk to Beach|1 Mi to Town
3 bedrooms, 5 beds, 1.5 bathrooms
7–12 Sept
Home in Greenport
Little House on Center Street
2 bedrooms, 2 queen beds, 1.5 bathrooms
7–12 Sept
New place to stay
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Greenport
Vintage 1880 Victorian gem.
1 bedroom, 2 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds, 4 bathrooms
8–15 Sept
4.97 out of 5 average rating, 114 reviews
Guest favourite
Home in Shelter Island
Hay Beach Family Home: Fire Pit, Playroom, Yard
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.9 out of 5 average rating, 130 reviews
Home in Orient
Brand new 4 bedrm 4.5 bath home with pool & beach
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 514 reviews
Guest favourite
Home in Greenport
Greenport Village Getaway
4 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
Guest favourite
Home in Orient
North Fork Modern Farmhouse
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Greenport
Cozy village home
1 double bed, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 215 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 178 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.96 out of 5 average rating, 100 reviews
Guest favourite
Home in Greenport
Renovated 1870’s farmhouse
3 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.88 out of 5 average rating, 49 reviews
Guest favourite
Home in Greenport
Freshly renovated farmhouse
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 54 reviews