Ski-in/Ski-out holiday rentals in Hudson Valley

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Cozy Lakeside Cottage w Year Round Hot Tub

Surrounded by peaceful forest this picturesque retreat is only 1hr30 from NYC and less than 2hrs from Philly! A sunny deck overlooks the lake and backyard filled with wildlife. This cottage has been designed with warm, stylish touches that emphasize comfort and relaxation. Enjoy a cozy fireplace, steamy hot tub, plenty of games, fast wifi, kayaks, SUPs. Minutes away: Shawnee Mountain(skiing),Breweries&Wineries, golfcourses and the Delaware National Rec area (hiking, biking, river excursions)!

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Enchanted Woodstock Cottage with great hot tub

Stunning Woodstock home with great fireplace and outdoor hot tub in secluded wooded area yet only six minutes to the town of Woodstock! Near skiing,hiking and lakes. Cherry wood radiant heat floors, skylights and a stunning bluestone fireplace and piano. Three bedrooms- (two with queen beds/third room opens to deck with full-size bed. One bath. Thirty minutes to skiing! The indoor heated porch has amazing views, and the dining room is right off the kitchen, where you can enjoy beautiful meals.

Luxe 2-Bed/2.5-Bath: Sleeps 8, Breakfast/Ski/Views

Beautiful luxe townhouse for up to 8 guests, with 2 bedrooms, 2.5 baths, a full kitchen, office, loft, and a deck with a grill overlooking parklike shared grounds. Bright interiors, skylights, mountain views, and a marble master shower will take your breath away. Steps from Shawnee Mountain and a short drive to Shawnee Inn & Golf, Bushkill Falls, the Delaware Water Gap, outlets, and dining. Includes breakfast, snacks, and quality body care—ideal for families, couples, or groups. Decor available.

Secluded Woodstock Retreat with Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

Only Ski In Out on Mtn | Hike, Golf, Fish, Unwind

Slopeside 1 bedroom that fits 4! Enjoy the hiking within a 5 minute drive or just walk out onto the mountain from your porch. Access to seasonal community pool with unbelievable mountain views! Unbeatable location on Hunter Mountain, short drive to town picturesque colorful village of Tannersville, majestic Kaaterskill Falls with hiking trails, and renown fishing! Fully stocked kitchen/bathroom, full entertainment system with Netflix and all of your favorite streaming services.

Skiiis N Tees • Mountain Views, Cozy Vibes

Skiiis N’ Tees is a 3-bedroom, 2-bath, four-season getaway where mountain views and fresh air do wonders for the soul. Just a short drive from NYC, it’s perfect for couples, families, girls weekends, or guys’ golf trips. This stylish end-unit condo sits beside a 9-hole golf course and is just 5 minutes from the slopes. Hike, sip at vineyards, or go apple picking—there’s something for everyone. One dog stays free. Pack & Play available. Come for the views and stay for the vibes!

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

Dome on Agroforestry Farm w/ Mountain View & Ponds

Welcome to The Dome on Long Future Farms! Our unique lodging is designed to provide a relaxing experience for 2-4 guests, with a focus on minimizing our environmental impact and supporting local ecological farming. (There are currently NO animals on the farm, as this is primarily a nut tree farm.) Our dome offers a breathtaking view of our 171-acre agroforestry land, hills and ponds, allowing you to truly connect with the natural beauty of the region.

Blackberry Cottage

Enjoy our peaceful (pet friendly) home, just a short drive to the center of Norfolk. Great for friends and/or family visits. Board games, puzzles and books inside for all; fire pit outside. Front & side decks, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. I think you’ll love it!

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.