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

Superhost
Home in Shelter Island
All Seasons Rental
3 beds
May 1 – 6
R18,835 ZAR for 5 nights
for 5 nights
4.72 out of 5 average rating, 39 reviews
Home in Shelter Island
New vacation house on the island(new pool)
Free cancellation
May 1 – 6
R83,095 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Cottage in Greenport
Coastal Cottage | 3-Min Walk to Beach, Near Town
Free cancellation
May 4 – 9
R32,993 ZAR for 5 nights, originally R39,779 ZAR
for 5 nights
5.0 out of 5 average rating, 5 reviews
Home in Shelter Island
Waterfront Heavenly Hideaway with separate casa
Free cancellation
May 1 – 6
R79,771 ZAR for 5 nights, originally R104,939 ZAR
for 5 nights
4.67 out of 5 average rating, 3 reviews
Guest favorite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
May 1 – 6
R19,388 ZAR for 5 nights, originally R21,253 ZAR
for 5 nights
4.89 out of 5 average rating, 95 reviews
Guest favorite
Home in Shelter Island
Moonlit Manor | Shelter Island Escape w/ NEW Sauna
3 beds
May 5 – 12
R56,505 ZAR for 7 nights
for 7 nights
4.92 out of 5 average rating, 12 reviews
Top guest favorite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4 beds
May 1 – 6
R59,052 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 105 reviews
Superhost
Room in Shelter Island
Stay with Susan CReal estate broker,
Magnolia Cape with private entrance & private bath
May 1 – 6
R25,482 ZAR for 5 nights
for 5 nights
4.71 out of 5 average rating, 21 reviews
Top guest favorite
Home in Shelter Island
Family Friendly Island Home
Free cancellation
May 30 – Jun 4
R78,663 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 80 reviews
Guest favorite
Home in Greenport
The Sandpiper
3 beds
May 11 – 16
R13,842 ZAR for 5 nights, originally R22,300 ZAR
for 5 nights
4.95 out of 5 average rating, 350 reviews
Top guest favorite
Room in Shelter Island
Stay with JimboMath teacher @ sihs,
Master Suite at RedHouse
May 1 – 6
R16,021 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 138 reviews
Guest favorite
Apartment in Shelter Island Heights
Squire Chase House
3 beds
May 1 – 6
R73,678 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 245 reviews
Home in Shelter Island
Spacious Shelter Island home near bay & beach
3 queen beds
Jun 13 – 18
R48,749 ZAR for 5 nights
for 5 nights
4.85 out of 5 average rating, 26 reviews
Home in Greenport
Charming Beachside Retreat - steps from beach
4 beds
May 18 – 23
R57,989 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
6 beds
May 16 – 21
R107,866 ZAR for 5 nights, originally R155,666 ZAR
for 5 nights
4.95 out of 5 average rating, 245 reviews
Guest favorite
Home in Shelter Island
Scandinavian family home on the water
3 beds
May 27 – Jun 1
R94,174 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 26 reviews
Guest favorite
Home in Greenport
Greenport Beach house Mini Resort Spa & Catering
Free cancellation
May 11 – 16
R50,854 ZAR for 5 nights, originally R69,590 ZAR
for 5 nights
4.9 out of 5 average rating, 207 reviews
Guest favorite
Home in Greenport
Cosy North Fork Cottage with large backyard
3 beds
May 18 – 23
R31,908 ZAR for 5 nights, originally R58,940 ZAR
for 5 nights
4.98 out of 5 average rating, 125 reviews