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

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Guest favorite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 queen bed

May 14 – 19

R19,039 ZAR for 5 nights, originally R20,869 ZAR

for 5 nights

4.89 out of 5 average rating, 95 reviews

Top guest favorite

Room in Shelter Island

Stay with JimboMath teacher @ sihs,

Master Suite at RedHouse

May 15 – 20

R15,092 ZAR for 5 nights

for 5 nights

4.93 out of 5 average rating, 138 reviews

Superhost

Home in Shelter Island

All Seasons Rental

3 beds

Aug 4 – 9

R29,375 ZAR for 5 nights

for 5 nights

4.73 out of 5 average rating, 40 reviews

Guest favorite

Cottage in Greenport

3-Min Walk to Beach | Baby & Beach Gear | Fire Pit

3 beds

May 18 – 23

R33,792 ZAR for 5 nights, originally R40,482 ZAR

for 5 nights

5.0 out of 5 average rating, 6 reviews

Guesthouse in Shelter Island

Lovely Island Cottage

1 bed

May 18 – 23

R33,725 ZAR for 5 nights

for 5 nights

4.88 out of 5 average rating, 33 reviews

Superhost

Room in Shelter Island

Stay with Susan CReal estate broker,

Magnolia Cape with private entrance & private bath

May 14 – 19

R25,022 ZAR for 5 nights

for 5 nights

4.71 out of 5 average rating, 21 reviews

Home in Shelter Island

Peaceful Bright Country House

3 beds

May 14 – 19

R36,663 ZAR for 5 nights

for 5 nights

Guest favorite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

4 beds

May 17 – 22

R42,430 ZAR for 5 nights

for 5 nights

4.78 out of 5 average rating, 55 reviews

Guest favorite

Home in Shelter Island

Moonlit Manor | Shelter Island Escape w/ NEW Sauna

3 beds

Jun 1 – 8

R51,677 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 15 – 20

R57,987 ZAR for 5 nights

for 5 nights

4.96 out of 5 average rating, 105 reviews

Top guest favorite

Apartment in Greenport

Waterfront Greenport Condo

4 beds

May 15 – 20

R27,633 ZAR for 5 nights, originally R40,393 ZAR

for 5 nights

5.0 out of 5 average rating, 8 reviews

Home in Shelter Island

Waterfront Heavenly Hideaway with separate casa

6 beds

May 14 – 19

R107,704 ZAR for 5 nights

for 5 nights

4.67 out of 5 average rating, 3 reviews

Guest favorite

Condo in Greenport

Beachside Waterview 2Br Condo w/ Pool in Greenport

3 beds

May 18 – 23

R23,575 ZAR for 5 nights, originally R25,525 ZAR

for 5 nights

4.92 out of 5 average rating, 138 reviews

Guest favorite

Home in Greenport

Greenport Beach house Mini Resort Spa & Catering

Free cancellation

May 18 – 23

R28,286 ZAR for 5 nights, originally R46,501 ZAR

for 5 nights

4.9 out of 5 average rating, 208 reviews

Guest favorite

Room in Shelter Island

Stay with Rosemary K

Grace House

May 19 – 24

R30,571 ZAR for 5 nights

for 5 nights

5.0 out of 5 average rating, 32 reviews

Guest favorite

Room in Shelter Island

Stay with JaneHosting for 8 years,

Room in Charming Coastal Cottage

May 18 – 23

R17,081 ZAR for 5 nights

for 5 nights

4.96 out of 5 average rating, 23 reviews

Guest favorite

Apartment in Shelter Island Heights

Squire Chase House

3 beds

May 15 – 20

R72,347 ZAR for 5 nights

for 5 nights

4.91 out of 5 average rating, 245 reviews

Top guest favorite

Home in Shelter Island

Family Friendly Island Home

Free cancellation

Jul 21 – 26

R76,460 ZAR for 5 nights

for 5 nights

4.93 out of 5 average rating, 80 reviews

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