filters

Search results; Over 1,000 homes in Shelter Island

Descriptions are based on details hosts provide
Top guest favourite
Home in Shelter Island Heights
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 private bathrooms
22–27 Sept
,
4.91 out of 5 average rating, 94 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 39 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
4.92 out of 5 average rating, 142 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 3 bathrooms
31 Jul – 5 Aug
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
15–20 Jul
Top guest favourite
Room in Shelter Island Heights
Master Suite at RedHouse
4.95 out of 5 average rating, 165 reviews, 1 king bed, 1 bathroom
16–21 Jul
Top guest favourite
Home in Shelter Island Heights
Private Hay Beach Retreat with Heated Pool
4.98 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 3 bathrooms
3–10 Aug
Guest favourite
Home in Shelter Island
Waterfront with kayaks, a hot tub, and fire pit
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
Top guest favourite
Cottage in Shelter Island
Tennis courts across the street, 4 bikes
4.97 out of 5 average rating, 120 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Shelter Island Heights
Huge yard with beach a bike away
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
4.83 out of 5 average rating, 42 reviews, 1 king bed, 1 bathroom
9–14 Aug
Guest favourite
Cottage in Shelter Island Heights
Large Waterfront Cottage on Historic Estate
4.84 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5.0 out of 5 average rating, 24 reviews, 5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
Top guest favourite
Cottage in Shelter Island Heights
Waterfront Getaway on Shelter Island
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Home in Shelter Island Heights
Indoor-outdoor living with a private pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Rooms in Shelter Island
Porch overlooking an 8-acre reserve
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Shelter Island Heights
Heated saltwater pool on Shelter Island
5.0 out of 5 average rating, 74 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
Guest favourite
Home in Shelter Island Heights
Water views on 3 sides with pool
4.95 out of 5 average rating, 74 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct