
Chalet holiday rentals in Long Island
Find and book unique chalets on Airbnb
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 chalet rentals in Long Island
Family-friendly chalet rentals

Chalet in Wainscott
4.55 out of 5 average rating, 11 reviewsRenovated One Bedroom Cottage by Ocean Beach
AlkaRating, 5 stars58 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 stars46 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 stars59 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!
Guest favourite

Chalet in Cold Spring
4.9 out of 5 average rating, 452 reviewsMountain View Retreat
AndrewRating, 5 stars1 week ago
Beautiful home, setting and back yard-deck sitting area right outside living room. Hot tub was relaxing. Hot water limited to four showers at a time due to water heater size I assume; however, it was never an issue during our stay (had 6 people).
Guest favourite

Private room in Stratford
4.86 out of 5 average rating, 372 reviewsComfy room - close to the beach and Universities
NicholasRating, 5 stars1 month ago
Eddys place was quite nice. I use Airbnb on a regular basis and have done so for 10 plus years and this was one of the best airbnb experience I've had. I was very happy with everything. Eddy seemed to be a great guy with a huge smile. I would recommend if you are in the area and are looking for an affordable place that's very peaceful.
Luxury chalet rentals

Chalet in Wainscott
4.55 out of 5 average rating, 11 reviewsRenovated One Bedroom Cottage by Ocean Beach
AlkaRating, 5 stars58 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 stars59 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!
Top guest favourite

Chalet in Redding
5 out of 5 average rating, 20 reviewsEnjoy our Connecticut Carriage House
JeremyRating, 5 stars1 week ago
The Carriage House is beautiful and Meredith and Mike are great hosts. The kitchen has everything you could ever need (not to mention arriving to a fridge with local milk and fresh eggs). The bedrooms and bathrooms are pristine. Mike even offered to help our son collect the eggs from the coop. All round exceptional stay.

Chalet in New Hyde Park
5 out of 5 average rating, 3 reviewsEscape to the Country Home/ Patio with Whirlpool
MärtRating, 5 stars1 month ago
The accommodation felt extremely homely. The surroundings were peaceful, with no hustle or noise. The 24/7 store was close enough to make for a pleasant walk for anyone feeling energetic in the evening or morning. The house itself felt like home right away, with delightfully creaky floors and enough space for both living and relaxing.
Superhost

Chalet in Vernon Township
4.8 out of 5 average rating, 100 reviewsVilla Adriana 4bdr 2 bath lake front dream home
LindiRating, 5 stars3 months ago
Michele’s place is terrific and Michele is a very attentive host.

Chalet in Wainscott
4.45 out of 5 average rating, 11 reviewsRenovatedOneBdrmCottageBy Ocean InHeartOf Hamptons
danielRating, 5 stars46 months ago
Great location, 1 mile from the beach They give you a beach parking pass, which is key!
Guest favourite

Chalet in Cold Spring
4.9 out of 5 average rating, 452 reviewsMountain View Retreat
AndrewRating, 5 stars1 week ago
Beautiful home, setting and back yard-deck sitting area right outside living room. Hot tub was relaxing. Hot water limited to four showers at a time due to water heater size I assume; however, it was never an issue during our stay (had 6 people).

Chalet in Bridgehampton
Enchanted Hamptons Cottage in NYTimes Garden
MasonRating, 5 stars26 months ago
Dianne and her cottage are truly one of a kind! I enjoyed every moment of my stay. The house and property couldn’t be any more charming and the location is absolutely perfect- close to beach and town. I would recommend this place 10/10.
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- Times Square
- Beach
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
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- Yale University
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- Citi Field
- MetLife Stadium
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- Gilgo Beach
- United Nations Headquarters
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- Statue of Liberty
- Bronx Zoo
- Radio City Music Hall
- Rockefeller Center
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