
Chalet vacation rentals in Long Island
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Top-rated chalet rentals in Long Island
Guests agree: these chalets are highly rated for location, cleanliness, and more.
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Popular amenities for Long Island chalet rentals
Family-friendly chalet rentals

Chalet in Wainscott
4.55 out of 5 average rating, 11 reviewsRenovated One Bedroom Cottage by Ocean Beach
AlkaRating, 5 stars56 months ago
The cottage is ideally situated and worked well for my family for last minute weekend getaway to Hamptons. The place is super clean and tidy, the host and on site property manager is very responsive and helpful. The place is small and just as described, was comfortable for my family of four. I want to emphasize the place was really clean and tidy, a bit dated but had its own charm. We also had a covered patio so didn’t feel tight or cramped. The cottage is also less than 2 miles from the beach. I would recommend the place for a couple and for a family with two small children as a base to visit the Hamptons and surrounding areas.

Chalet in Wainscott
4.45 out of 5 average rating, 11 reviewsRenovatedOneBdrmCottageBy Ocean InHeartOf Hamptons
danielRating, 5 stars45 months ago
Great location, 1 mile from the beach They give you a beach parking pass, which is key!

Chalet in Wainscott
4.31 out of 5 average rating, 13 reviewsRenovated Studio Cottage by Ocean
MattRating, 5 stars57 months ago
This was an absolutely fabulous place to stay! The grounds were in a lovely wooded area under the stars. Super clean, Bar B Q grill, great patio, large bed, fully functioning kitchen. Matt was excellent at providing information before hand, and responsive to queries. Super close to amazing hampton beaches, two mile hollow and beach lane. Also close to seafood mart with amazing lobster salad and a bagel place with iced coffee for the gays. Ask about the catch of the day. Loved it all!

Chalet in East Hampton
4.88 out of 5 average rating, 8 reviewsCharming House in E. Hampton (Price reduction)
JamieRating, 5 stars69 months ago
We loved the accommodations! The house had everything for our family of five (with three picky teenagers). Wish we had taken advantage of the big backyard, but our stay was just too short!
Guest favorite

Chalet in Cold Spring
4.9 out of 5 average rating, 442 reviewsMountain View Retreat
EllisaRating, 5 stars6 days ago
If you are looking for tranquility and views with all the amenities, this is the place for you. It’s located between Cold Spring and Beacon when you want to explore and eat or grab coffee. We didn’t use the hot tub or fire pit due to time constraints but instructions are available. Everything was made easy. The yard was fantastic for our small dogs to zoom around. The kitchen was fully equipped and again… the views!
Guest favorite

Private room in Stratford
4.86 out of 5 average rating, 370 reviewsComfy room - close to the beach and Universities
MattRating, 5 stars4 weeks ago
Eddy's place was easy to find and conveniently located near a lot of attractions, venues, and there was plenty of street parking available.
Luxury chalet rentals

Chalet in Wainscott
4.55 out of 5 average rating, 11 reviewsRenovated One Bedroom Cottage by Ocean Beach
AlkaRating, 5 stars56 months ago
The cottage is ideally situated and worked well for my family for last minute weekend getaway to Hamptons. The place is super clean and tidy, the host and on site property manager is very responsive and helpful. The place is small and just as described, was comfortable for my family of four. I want to emphasize the place was really clean and tidy, a bit dated but had its own charm. We also had a covered patio so didn’t feel tight or cramped. The cottage is also less than 2 miles from the beach. I would recommend the place for a couple and for a family with two small children as a base to visit the Hamptons and surrounding areas.

Chalet in Wainscott
4.31 out of 5 average rating, 13 reviewsRenovated Studio Cottage by Ocean
MattRating, 5 stars57 months ago
This was an absolutely fabulous place to stay! The grounds were in a lovely wooded area under the stars. Super clean, Bar B Q grill, great patio, large bed, fully functioning kitchen. Matt was excellent at providing information before hand, and responsive to queries. Super close to amazing hampton beaches, two mile hollow and beach lane. Also close to seafood mart with amazing lobster salad and a bagel place with iced coffee for the gays. Ask about the catch of the day. Loved it all!

Chalet in East Hampton
4.88 out of 5 average rating, 8 reviewsCharming House in E. Hampton (Price reduction)
JamieRating, 5 stars69 months ago
We loved the accommodations! The house had everything for our family of five (with three picky teenagers). Wish we had taken advantage of the big backyard, but our stay was just too short!
Guest favorite

Chalet in Rock Tavern
4.96 out of 5 average rating, 24 reviewsArchitect’s Cottage in the Woods
EricRating, 5 stars8 months ago
We had an amazing stay at Diane & Brice's place. So quiet and secluded, surrounded by forest on all sides. Amazing design and decor - a perfect balance of well-designed and warm, the space is inviting and relaxing to be in. Lots of places to hang both indoors and outdoors. And the pool! Salt water surrounded on three sides by trees.
Top guest favorite

Chalet in Redding
5 out of 5 average rating, 18 reviewsEnjoy our Connecticut Carriage House
MeriRating, 5 stars4 months ago
A beautiful home, perfect for our family early Christmas get together. Meredith went above and beyond to decorate the home, Christmas tree and all, to make us feel at home. Amazing kitchen - enjoyed by the cooks in the family.
Superhost

Chalet in Vernon Township
4.8 out of 5 average rating, 100 reviewsVilla Adriana 4bdr 2 bath lake front dream home
LindiRating, 5 stars2 months ago
Michele’s place is terrific and Michele is a very attentive host.

Chalet in Vernon Township
4.82 out of 5 average rating, 196 reviewsPrivate Chalet Ski/Pools/Golf/Mountain Creek/Hike
SantiagoRating, 5 stars2 months ago
Thank you so much, our family really appreciated it the quick and personal response to our inquiries, the place was extremely clean and comfortable we will definitely stay again and will highly recommend your home to our family and friends, also before I forget the location was perfect very accessible and within steps of the sky resort, thank you
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- Radio City Music Hall
- Beach
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
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- Riverside Park
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- Yale University
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- Gilgo Beach
- St. Nicholas Park
- Citi Field
- Yankee Stadium
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- Inwood Hill Park
- United Nations Headquarters
- Bronx Zoo
- Astoria Park
- Statue of Liberty
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