Chalet holiday rentals in Orange County

Luxe Retreat with Fireplace/Pool near Water Parks

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.

Hudson Valley A-Frame-Movies~Arcade~HTub~60-mi~NYC

The charm of Upstate NY meets the adventure of the Poconos—right at your doorstep. Unwind and Recharge at our serene, one of a kind A-frame nestled on 4 private acres. Enjoy a sunken hot tub, chef’s kitchen, 135" theater, arcade, fire pit and a tranquil creek running through, providing a soothing soundtrack to your stay. Located at a unique tristate meeting point surrounded by charming towns, local farms, vineyards, near by activities like hiking, skiing, sky diving and water sports. NO PETS

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.

Riverfront Ski Chalet

Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

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.

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 heated 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.

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.

Beautiful Mountain Retreat - Wurtsboro, NY

Beautiful chalet house with screened in porch. Approx. 500 feet from the private lake. A short walk or a 30 second car ride. House features 2 bedrooms, 2 full baths, a loft with a full size bed (3rd Bedroom), couch, and fireplace. Two air conditioner units and heating. There's an eat-in full equipped kitchen. Washer, dryer located in basement. We have a rowboat and 3 kayaks to use at lake. We have an outdoor fire pit by the house.

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.