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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Top guest favourite

Chalet in Warwick

5 out of 5 average rating, 17 reviews

Warwick Bellvale Mtn. House, Spectacular Views!

A winter wonderland mountain escape, Warwick's own Bellvale Mountain House, a 4-bedroom, 2 full bath, Craftsman style single family 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, a 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.

Guest favourite

Private room in Stratford

4.78 out of 5 average rating, 50 reviews

Beautiful room- near beach and universities

Available for long term(at least 2 nights). Private bedroom with 1 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

Chalet in Greenport

5 out of 5 average rating, 13 reviews

Luxury A-Frame Retreat Near the Water

Escape to a Luxury winter retreat at our stunning designer chalet by the Peconic Bay in Greenport, NY. With 4 bedrooms, 3 baths, and a warm inviting loft, it’s ideal for a snowy weekend escape, team retreat, or midwinter recharge. Unwind by two fireplaces, cook comfort meals in the well-equipt kitchen, watch movies in ATMOS tv-room, visit nearby wineries and farm stands, or walk the quiet winter beach just steps from the house. A serene, design-forward haven to watch the season unfold.

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, 57 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.

The interior of a spacious platform tent is shown, featuring two queen beds with clean linens and a dresser. Natural light enters through the open sides, highlighting the nearby greenery. A geometric patterned rug is positioned on the floor, complementing the rustic decor.

Chalet in Patchogue

26-D Glamping - Fire Island - Watch Hill

Glamp at the beach at Fire Island National Seashore. Your adventure begins the minute you board the ferry. Furnished Safari platform tents with linens, behind primary dune, a short walk to life guarded ocean beach. Hike the pristine high dune wilderness. Enjoy beach, fishing, clamming, sunsets, sunrises, wildlife, & whale sightings, a perfect family destination spring/summer/fall. NPS rangers w/Jr Ranger program, guided nature & kayak tours. Eat & drink at our outdoor restaurant

Guest favourite

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

4.94 out of 5 average rating, 17 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.

Superhost

Private room in Stratford

4.86 out of 5 average rating, 383 reviews

Comfy room - close to the beach and Universities

Private bedroom with 1 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 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

Chalet in Warwick

4.93 out of 5 average rating, 136 reviews

Mountain Luxury: Pool, Theater & Outdoor Kitchen

Permit #P25-0159 Discover the perfect blend of mountain charm and luxury on several acres just minutes from Downtown Warwick. This serene retreat features stunning Hudson Valley views, a heated pool, covered outdoor kitchen with fireplace, and elegant indoor spaces including a Great Room and cinematic media room. Enjoy wineries, orchards, hiking, skiing, and more all within 15 minutes and just one hour from Manhattan.

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, 25 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.