filters

Search results; Over 1,000 homes in Shelter Island Heights

Superhost
Flat in Shelter Island Heights
Squire Chase House
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
,
4.9 out of 5 average rating, 262 reviews
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
6–11 Sept
4.94 out of 5 average rating, 35 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds
13–20 Jul
New place to stay
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
12–17 Jul
4.97 out of 5 average rating, 117 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 23 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
1–6 Aug
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
23–28 Jul
4.91 out of 5 average rating, 91 reviews
Top guest favourite
Rooms in Shelter Island
Grace House
2 bedrooms, 2 beds
12–17 Jul
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Greenport
Corwin House
4 bedrooms, 4 beds
12–18 Oct
4.98 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
13–18 Sept
4.84 out of 5 average rating, 73 reviews
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds
11–16 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds
14–19 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Greenport
Beach House in L.I. Wine Country
3 bedrooms, 4 beds
7–12 Sept
4.99 out of 5 average rating, 118 reviews
Home in Shelter Island
60's Ranch meets the Mediterranean
3 bedrooms, 4 beds
1–6 Jun
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds
20–25 Sept
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
26–31 Jul
5.0 out of 5 average rating, 88 reviews
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed
1–6 Jul
4.91 out of 5 average rating, 45 reviews
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds
13–18 Jul