filters

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

Photo 1 of 6
Apartment in Shelter Island Heights
Shelter Island Waterview Villa
1 bedroom, 2 beds, 1 private bathroom
17–22 Sept
,
5.0 out of 5 average rating, 3 reviews
Photo 1 of 16
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 11 reviews
Photo 1 of 20
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 161 reviews
Photo 1 of 6
Guest favourite
Room in Shelter Island Heights
SEVEN on Shelter - Queen Room w/Private Bathroom
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 23 reviews
Photo 1 of 18
Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
New place to stay
Photo 1 of 29
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 32 reviews
Photo 1 of 6
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 154 reviews
Photo 1 of 6
Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 174 reviews
Photo 1 of 29
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Photo 1 of 29
Guest favourite
Flat in Greenport
Harbor Heights
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 247 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island
Shelter Island Beauty w/Pool; Beaches/Golf/Tennis
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 77 reviews
Photo 1 of 6
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 161 reviews
Photo 1 of 24
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
6 bedrooms, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
Photo 1 of 28
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 57 reviews
Photo 1 of 26
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 79 reviews
Photo 1 of 29
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.92 out of 5 average rating, 100 reviews
Photo 1 of 6
Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 50 reviews