Chalet holiday rentals in Long Island

Find and book unique chalets on Airbnb

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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 reviews

Renovated 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 reviews

RenovatedOneBdrmCottageBy 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 reviews

Renovated 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, 454 reviews

Mountain View Retreat

RistiRating, 5 stars1 week ago
Linda is such a great host! She is SUPER organized from the very beginning giving us clear instructions about the check in, the rules at the house, leaving printed version of all of that in different sides of the house, and even to the way she organized and provided everything we ever needed at that house. And the house itself is soooo gorgeous and peaceful I felt right at home. The only flaw is that it has bad reception in the area since it is surrounded by woods. But Linda provided us with strong wifi in the house, so I guess that settled it.
Guest favourite
Private room in Stratford
4.86 out of 5 average rating, 374 reviews

Comfy room - close to the beach and Universities

JacquelineRating, 5 stars2 weeks ago
Great bedroom, great area! It is very good size bedroom, it looks smaller in the pictures It has a small fridge and small microwave , a dresser, fan , AC. small TV. Very very Comfortable bed, nice and clean. The bathroom is right outside the room and just for the Airbnb guests. I did not have any problem with the shower and I am 5' 8" Peaceful neighborhood.

Luxury chalet rentals

Chalet in Wainscott
4.55 out of 5 average rating, 11 reviews

Renovated 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 reviews

Renovated 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 Port Jervis
5 out of 5 average rating, 5 reviews

Exquisite A-Frame-Movies~Arcade~HTub~60-mi~NYC

EduardoRating, 5 stars2 weeks ago
This was a beautiful home and the hosts were very helpful and accommodating! I’m super thankful to have spent my 40th birthday here with friends. I absolutely loved the space, amenities, and I would love to come back. Thank you so much for the hospitality! Beautiful home and managed by great people - I’ll definitely come back again soon. Thank you!
Guest favourite
Chalet in Rock Tavern
4.96 out of 5 average rating, 24 reviews

Architect’s Cottage in the Woods

EricRating, 5 stars9 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 favourite
Chalet in Redding
5 out of 5 average rating, 20 reviews

Enjoy our Connecticut Carriage House

JeremyRating, 5 stars3 weeks 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, 4 reviews

Escape to the Country Home/ Patio with Whirlpool

VanessaRating, 5 stars1 month ago
The home was extremely comfortable and homey. The pictures did not do the house justice. It was in a nice, quiet neighborhood that was just a short drive from shops. The beds were super comfy. Manuel was friendly and communicative. It truly felt like a home away from home.
Superhost
Chalet in Vernon Township
4.8 out of 5 average rating, 100 reviews

Villa 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 reviews

RenovatedOneBdrmCottageBy 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!

Lakefront chalet rentals

Top Guest favourite
Chalet in Port Jervis
5 out of 5 average rating, 5 reviews

Exquisite A-Frame-Movies~Arcade~HTub~60-mi~NYC

EduardoRating, 5 stars2 weeks ago
This was a beautiful home and the hosts were very helpful and accommodating! I’m super thankful to have spent my 40th birthday here with friends. I absolutely loved the space, amenities, and I would love to come back. Thank you so much for the hospitality! Beautiful home and managed by great people - I’ll definitely come back again soon. Thank you!
Guest favourite
Chalet in Carmel Hamlet
4.97 out of 5 average rating, 76 reviews

Secluded Lakefront Chalet-Firepit+Yard Dogfriendly

IzzyRating, 5 stars2 weeks ago
I cannot recommend Wylda's place enough! This was absolutely nothing short of a 5 star stay. Accurate listing, a beautiful and comfy home, and an unbelievably stunning, secluded, and private property tucked into nature, between two lakes no less!! I came here to get away from it all, and this property exceeded my expectations. The amount of birds you'll hear singing through all parts of the day almost doesn't even feel real. Not to mention, Wylda is a wonderful host. I will absolutely be back here again!!
Superhost
Chalet in Vernon Township
4.8 out of 5 average rating, 100 reviews

Villa 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.
Guest favourite
Chalet in Vernon Township
4.88 out of 5 average rating, 165 reviews

Dream Lakefront Escape + Beach/Ski/Golf near NYC

JonathanRating, 5 stars3 weeks ago
Alessandra’s place was great! Host was very responsive. House was very clean and the views were amazing. Would definitely stay again. Thank you!

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