Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.

Shelter Island Chalets

Bundle & Save

Get more, spend less whenever you see Bundle & Save deals

OneKeyCash

Earn OneKeyCash on all your eligible bookings

Upfront pricing

We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Chalets in Shelter Island

We don't have any properties that match your exact search

See all properties in Shelter Island

Recommended hotels in Shelter Island

"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "

$1,257 nightly

Nov 5 - Nov 6

Total with taxes and fees

"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

$85 nightly

Oct 14 - Oct 15

Total with taxes and fees

"Great staff and clean rooms"

$78 nightly

Oct 14 - Oct 15

Total with taxes and fees

"The beach view is spectacular the surrounding area has everything you need for a each getaway"

$119 nightly

Nov 9 - Nov 10

Total with taxes and fees

"Beautiful grounds, excellent staff"

$143 nightly

Nov 3 - Nov 4

Total with taxes and fees

Seasonal outdoor pool, pool umbrellas, sun loungers

"Love this place. "

$120 nightly

Nov 2 - Nov 3

Total with taxes and fees

"We have stayed there before so have been pleased with it."

$94 nightly

Nov 2 - Nov 3

Total with taxes and fees

"Great place "

$249 nightly

Oct 27 - Oct 28

Total with taxes and fees

"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"

$121 nightly

Nov 2 - Nov 3

Total with taxes and fees

"the so-called breakfast was absolute minimum only thing available was make your own waffle"

$72 nightly

Nov 2 - Nov 3

Total with taxes and fees

One Bedroom Harbor View Terrace Suite | View from room

"Great location ,beautiful hotel,nice staff"

$208 nightly

Nov 2 - Nov 3

Total with taxes and fees

"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."

$134 nightly

Oct 27 - Oct 28

Total with taxes and fees

"Loved the overall stay and experience. The private beach access is a bonus"

$168 nightly

Oct 27 - Oct 28

Total with taxes and fees

"Great Staff"

$137 nightly

Nov 2 - Nov 3

Total with taxes and fees

Studio Unit Upper Oceanfront 'San Remo' | Terrace/patio

"Perfect location!"

$191 nightly

Oct 28 - Oct 29

Total with taxes and fees

"Clean, cute property with super friendly staff. Breakfast was an added bonus."

$169 nightly

Nov 2 - Nov 3

Total with taxes and fees

"Staff was amazing and this hotel is in the perfect location "

$156 nightly

Oct 14 - Oct 15

Total with taxes and fees

"This place was very nice and quiet. "

$201 nightly

Oct 27 - Oct 28

Total with taxes and fees

"Well located for getting to the places we wanted to be. This is an older property, but well taken care of and service was very good. I wouldn’t hesitate to stay here again. "

$77 nightly

Nov 12 - Nov 13

Total with taxes and fees