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Search Chalets in Shelter Island Heights

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Shelter Island Heights Chalets

The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The Pridwin Hotel
The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (29)
"Excellent "
The price is CA $445
CA $509 total
includes taxes & fees
Apr 6 - Apr 7
The Chequit
SEVEN - Shelter Island Guest House
Beach nearby, white sand, sun loungers, beach umbrellas

SEVEN - Shelter Island Guest House

2.5 star property
9.8 out of 10, Exceptional, (57)
"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"
SEVEN - Shelter Island Guest House
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (69)
"Beautiful setting and big rooms close to ferry and town center. "
The price is CA $173
CA $198 total
includes taxes & fees
Apr 7 - Apr 8
House on Chase Creek
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
The Rams Head Inn
Exterior

The Rams Head Inn

4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
The Rams Head Inn
Shelter Island House
Terrace/patio

Shelter Island House

3.5 star property
8.4 out of 10, Very good, (56)
"Everything was excellent. However, it would have been nice if there had been something offered for breakfast."
Shelter Island House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Shelter Island Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1149)
"the location is great and price is reasonable. "
The price is CA $209
CA $266 total
includes taxes & fees
Apr 21 - Apr 22
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (368)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is CA $192
CA $234 total
includes taxes & fees
Apr 9 - Apr 10
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"2nd loft bedroom/bath was especially nice"
The price is CA $186
CA $243 total
includes taxes & fees
Apr 6 - Apr 7
Windward Shores Ocean Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.