Chalet vacation rentals in Long Island

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Popular amenities for Long Island chalet rentals

Family-friendly chalet rentals

A serene outdoor landscape features a well-maintained path of brick leading toward a green-roofed cottage, surrounded by lush grass and mature trees. Neatly trimmed shrubs are seen framing the scene, providing a tranquil setting.
Chalet in Wainscott
4.55 out of 5 average rating, 11 reviews

Renovated 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.
A charming cottage is set within a lush green landscape, featuring a screened patio with wicker furniture. The home is adorned with green shutters, and a walkway leads to the front door, framed by trees and vibrant grass.
Chalet in Wainscott
4.45 out of 5 average rating, 11 reviews

RenovatedOneBdrmCottageBy 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!
A quaint entrance is framed by green bushes and vibrant pots filled with colorful flowers. A stone pathway leads to a screened door, while a grill is positioned nearby, offering an inviting outdoor space.
Chalet in Wainscott
4.31 out of 5 average rating, 13 reviews

Renovated 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 reviews

Charming 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
Natural light floods a living area through large glass doors, which provide views of the garden and mountains. A comfortable couch faces a wooden coffee table, and a fireplace is situated beside a bookshelf filled with books. Decorative art enhances the space.
Chalet in Cold Spring
4.9 out of 5 average rating, 442 reviews

Mountain 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
A private bedroom features a dark wood bed with a blue-green bedspread and decorative pillow. Natural light enters through a window covered with light curtains. A patterned area rug is placed beneath a nightstand with a lamp, complementing the room's décor.
Private room in Stratford
4.86 out of 5 average rating, 370 reviews

Comfy 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

A serene outdoor landscape features a well-maintained path of brick leading toward a green-roofed cottage, surrounded by lush grass and mature trees. Neatly trimmed shrubs are seen framing the scene, providing a tranquil setting.
Chalet in Wainscott
4.55 out of 5 average rating, 11 reviews

Renovated 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.
A blooming cherry blossom tree with vibrant pink flowers stands in a green yard. Nearby, wooden picnic tables are set on the grass, surrounded by lush foliage. Sunlight filters through the tree branches, creating a serene outdoor atmosphere.
Chalet in Wainscott
4.31 out of 5 average rating, 13 reviews

Renovated 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!
A bright and airy living space is defined by large glass doors leading to the garden. A white sofa with patterned cushions is arranged on a textured area rug, accompanied by a wooden rocking chair. Warm wooden beams accent the ceiling, contributing to the inviting atmosphere.
Chalet in East Hampton
4.88 out of 5 average rating, 8 reviews

Charming 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
A serene swimming pool is framed by lush greenery, with a wooden shed visible in the background. Multiple lounge chairs are positioned around the pool area on a concrete deck, offering a tranquil space for relaxation.
Chalet in Rock Tavern
4.96 out of 5 average rating, 24 reviews

Architect’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
The exterior of a charming three-story carriage house is showcased, surrounded by vibrant autumn foliage. A cupola tops the structure, adding a unique architectural detail. Adjacent is a black barn, complementing the scenic landscape on a clear, sunny day.
Chalet in Redding
5 out of 5 average rating, 18 reviews

Enjoy 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 reviews

Villa 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.
An outdoor pool is situated amidst a snowy landscape, surrounded by lush greenery. Guests enjoy the water while the large glass structure of the resort offers a warm contrast to the winter environment. The scene showcases a clear blue sky, enhancing the ambiance.
Chalet in Vernon Township
4.82 out of 5 average rating, 196 reviews

Private 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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