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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
20–25 Sept
,
4.9 out of 5 average rating, 271 reviews
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 11 reviews
Featured hotel
Hotel in Greenport
King Suite
1 bedroom, 1 king bed, 1 bathroom
29 Sept – 4 Oct
New place to stay
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
Guest favourite
Home in Shelter Island
Family Friendly Modern Island Home Steps to Beach!
4 bedrooms, 7 beds, 3.5 bathrooms
15–20 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 130 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 23 reviews
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
Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 26 reviews
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
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, 160 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 Shelter Island
Shelter Island Beauty w/Pool; Beaches/Golf/Tennis
4 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
25–30 Sept
4.94 out of 5 average rating, 171 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Home in Shelter Island
Chic, serene, designer home with pool and views
4 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
4.98 out of 5 average rating, 44 reviews
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, 153 reviews