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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Chalet in East Hampton

4.88 out of 5 average rating, 8 reviews

Charming House in E. Hampton (Price reduction)

Relax in the hammock, go to the beach, bike to the farmers market or cuddle up by the fire, and enjoy our peaceful home as your own. Five minutes drive to East Hampton and Amagansett beaches and towns. Three bedrooms and two baths. Sleek and beautiful decorated the house has top of the line chef’s dream kitchen. Hughe den facing an enormous garden with old trees, flowers and a fenced herb garden. Cozy space to enjoy a large Samsung TV and Bose sound system. Large dining areas inside and outside.

Chalet in Sussex

4.65 out of 5 average rating, 17 reviews

Luxe Retreat with Fireplace/WiFi in Ski Country

This stylish home is perfect for groups, festivities of any type. The pool is centrally located in an open floor plan and doorsteps to chef's kitchen for endless entertainment. Thereupon, settle by the fireplace where each crackle from the flaming timber inches you closer to dream wonderland. The spacious bedrooms include a master-suit with all the amenities for the perfect getaway. Wake up to nature greeting you with fresh pine aromas all around as you step out the balcony and take it all in.

Guest favourite

Chalet in Vernon Township

4.89 out of 5 average rating, 159 reviews

Dream Lakefront Escape + Beach/Ski/Golf near NYC

Discover an exclusive, light-filled lakefront sanctuary just one hour from NYC — stylishly minimalistic and impeccably clean. This 3BR, 2-bath chalet on Highland Lake offers a luxurious retreat for small families, couples, or friends, perfect for every season. Enjoy private access to a sprawling dock with fire pit, grill, canoe, kayaks, paddle boards — your personal lake paradise — near Mountain Creek Ski Resort, Spa, Waterpark, private beaches, golf, and hiking. Wedding packages available.

Chalet in Southampton

4.33 out of 5 average rating, 9 reviews

Private & Serene Lakefront Cottage

Relax, rejuvenate and unplug in this one acre lakeside hidden gem in Southampton. The rustic, lofted spacious 4 Br 2.5 Ba chalet features wood, stone and marble construction and eclectic vibe. Enjoy serenity on Big Fresh Pond, the second largest fresh water lake in Long Island ideal for swimming, kayaking, skating or sipping wine on a private deck. Walk into the wetland nature reserve or take a quick 5-10 min ride to the one of the many famous ocean/bay beaches and the Town of Southampton.

Chalet in Patchogue

New place to stay

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

Chalet in Vernon Township

4.82 out of 5 average rating, 196 reviews

Private Chalet Ski/Pools/Golf/Mountain Creek/Hike

Escape to this rare, private ski chalet for 10 in Vernon Township, nestled within Crystal Springs Resort. This cozy mountainside retreat features 5 uniquely themed bedrooms, 2 decks, and a warm, inviting atmosphere. Enjoy nearby adventures like skiing, snowboarding, mountain biking, family-friendly activities, pool, hot tub, hiking, wildlife viewing, horseback riding, lakes, the Appalachian trail and more! We are next door to Mountain creek, ideal for a family or group of friends.

Guest favourite

Chalet in Rock Tavern

4.96 out of 5 average rating, 24 reviews

Architect’s Cottage in the Woods

NEW: Swimming Pool! Relax in this calm, stylish house inspired by Frank Lloyd Wright. House fully renovated with all modern amenities. The living room with cathedral ceiling offers stunning views to the forest. The place is secluded in the middle of a private 7-acre wooded backyard, despite being only 1h North from the GW Bridge. Enjoy the saltwater swimming pool (seasonal), a BBQ on the deck or a drink by the fire pit. Relax by the wood burning stove in the evening.

Guest favourite

Private room in Stratford

4.86 out of 5 average rating, 371 reviews

Comfy room - close to the 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 bedroom key is provided. 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.

Superhost

Chalet in Vernon Township

4.8 out of 5 average rating, 100 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

Chalet in Cold Spring

4.9 out of 5 average rating, 444 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.

Superhost

Chalet in West Milford

4.93 out of 5 average rating, 45 reviews

Serene Getaway with Seasonal Pool and Hot Tub

Our modern farmhouse is the ideal getaway destination to escape from the city. Located only an hour away from New York City, this secluded sanctuary is nestled between Warwick, Greenwood Lake, and Vernon, NJ. It is newly renovated with a host of amenities (in-ground pool, jacuzzi, central air, wood stove, washer and dryer) and is conveniently located near many year around attractions.