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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Superhost

Private room in Stratford

4.74 out of 5 average rating, 42 reviews

Beautiful room- near beach and universities

Available for long term(at least 2 nights). Private bedroom with Queen Bed, TV, WiFi, Mini Fridge, Microwave, Heat and A/C. A passcode is provided to unlock front and bedroom doors. Bathroom is shared with airbnb guest only. LOW SLANTED CEILING BATHROOM - fit 5'10'' and under. Nice, and quiet neighborhood. Close to Merritt Pkwy, I-95, Train station , and Beaches. Please note that the room is bigger than what it appears in the posted photos. House#435 is on the right of #439 and 437.

Guest favourite

A sunlit open living area features large windows and skylights that showcase serene lake views. A comfortable couch sits next to a television, while a dining table accommodates six chairs. The natural light enhances the warm tones of the wooden floor, creating a welcoming ambiance.

Chalet in Vernon Township

4.88 out of 5 average rating, 178 reviews

Dream Lakefront Escape + Beach/Ski/Golf near NYC

EXCITING UPDATES: Closed Oct 27-Dec 31, 2025 for renovations. Reopening Jan 1, 2026 with NEW hot tub, sauna, modern kitchen & bathrooms! Exclusive lakefront sanctuary 1hr from NYC — stylishly minimalist & impeccably clean. This 3BR, 2-bath chalet on Highland Lake offers luxury for families, couples or friends. Private dock with fire pit, grill, canoe, kayaks, paddle boards. 10min to Mountain Creek Ski Resort. Spa, waterpark, beaches, golf & hiking nearby. Wedding packages available.

Guest favourite

An outdoor pool area is surrounded by lush greenery, offering a serene escape. Two lounge chairs are positioned beside the pool, along with a large umbrella. The pool's clear blue water reflects the sunlight, and a flower pot adds a pop of color nearby.

Chalet in West Milford

4.91 out of 5 average rating, 55 reviews

Chalet w/ Hot Tub, Bar & Game Room– 1 Hr from NYC!

Unwind in a sun-filled glass chalet with panoramic forest views. Sip cocktails at your private bar, challenge friends to arcade games, and relax under the stars in your secluded hot tub. Located only an hour away from New York City, this secluded sanctuary is nestled between Warwick, Greenwood Lake, and Vernon, NJ. It is with a host of amenities (in-ground pool, jacuzzi, central air, wood stove Fireplace washer and dryer) and is conveniently located near many year around attractions.

Guest favourite

Chalet in Warwick

5 out of 5 average rating, 9 reviews

Warwick Bellvale Mtn. House, Spectacular Views!

Warwick's own Bellvale Mountain House, a 3-bedroom, 2 full baths with bonus room, 2 bath Craftsman style home perched on the top of Mt. Peter with breathtaking views of the Warwick Valley, this is the place to stay. Secluded, quiet and spacious, the perfect place to unwind and relax. Steps away from everything Warwick and Greenwood Lake have to offer yet secluded enough to create a perfect sanctuary for your visit. Please feel free to inquire about any other details.

An outdoor whirlpool is positioned on a gravel patch surrounded by grass, featuring steps that provide access to the tub. The cover is partially open, revealing bubbling water. Smaller lights are visible along the perimeter, enhancing the inviting setting.

Chalet in New Hyde Park

5 out of 5 average rating, 7 reviews

Escape to the Country Home/ Patio with Whirlpool

Welcome to Manhasset Hills. We invite you to a comfortable, spacious and elegant three-bedroom home. The home is equipped with all the commodities of a home for comfort living. Throughout the four seasons, soak sore muscles and relax in the backyard by the patio in our outdoor whirlpool. The patio is fully furnished with patio furniture and a barbecue. On rainy days enjoy cocktails indoors in the entertainment room playing billiards at this peaceful escape.

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

Ideal place in prime location to enjoy Bridgehampton East Hampton & Sag Harbor Bike to beach vineyard golf range & farm stand. Air-conditioning, flat screen cab tv WiFi, private screen patio with wicker furniture. Close to public transport, art and culture. You’ll love my place because of the location and the coziness My place is good for couples, solo adventurers, business travelers, families (with kids) and friendly for pets. Sorry no cats.

Guest favourite

Private room in Stratford

4.86 out of 5 average rating, 381 reviews

Comfy room - close to the beach and Universities

Private bedroom with Queen Bed, TV, WiFi, Mini Fridge, Microwave, Heat and A/C. A passcode is provided to unlock front and bedroom doors. Bathroom is shared with airbnb guests only. LOW SLANTED CEILING BATHROOM - fit 5'10'' and under. Nice, and quiet neighborhood. Close to Merritt Pkwy, I-95, Train station , and Beaches. Please note that the room is bigger than what it appears in the posted photos. House#435 is on the right of #439 and 437.

A tranquil lakeside view is presented, showcasing vibrant colors reflecting on the water at sunset. A wooden dock is seen with kayaks and stand-up paddleboards resting near the shore, surrounded by lush trees and serene nature.

Chalet in Vernon Township

4.78 out of 5 average rating, 106 reviews

Villa Adriana 4bdr 2 bath lake front dream home

Hello&welcome to Villa Adriana! Immersed amongst the trees and surrounding garden, perched on a slope overlooking Highland Lake, Villa Adriana is considered to have one of the best views of the entire lake. You can enjoy the spectacular view from the comfort of a cozy living room with large windows overlooking the lake, and from the adjacent roomy outdoor deck equipped with table, chairs, umbrella, and a BBQ grill for dining al fresco.

Guest favourite

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, 481 reviews

Mountain View Retreat

15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

A charming cottage is framed by lush greenery, featuring light yellow siding and green shutters. A small porch with a green awning is visible, while a path leads through the manicured lawn. A grill is placed nearby, adding to the serene outdoor setting.

Chalet in Wainscott

4.55 out of 5 average rating, 11 reviews

Renovated One Bedroom Cottage by Ocean Beach

Ideal place in prime location to enjoy Bridgehampton East Hampton & Sag Harbor Bike to beach vineyard golf range & farm stand Renovated Cottage - AC flat scrn cab tv WiFi full bath kitchenette gas range priv scrn patio wicker furnitur

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

Top Guest favourite

The exterior of the carriage house is shown, showcasing a charming design with curved garage doors. A spacious lawn features neatly trimmed grass, a decorative planter, and a large tree providing shade in a serene, natural setting.

Chalet in Redding

5 out of 5 average rating, 24 reviews

Enjoy our Connecticut Carriage House

Enjoy our extraordinary, 3-story carriage house with cozy fireplace & outdoor fire pit. Family-friendly with lots of room and outdoor space. Walking distance to Topstone Park and local New Pond Farm.