Chalet vacation rentals in Hudson Valley

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

Winter Paradise w/ Stunning Views Near Windham Mtn

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Modern Mountain Chalet on 15 Acre Catskills Estate

This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

Spacious cabin w/grill, firepit & mountain views

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

Sunday Mountain House - Cozy Catskills Chalet

Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Catskill Mountains. Our home is located about 2-2.5 hours from NYC, and minutes from the charming towns of Roscoe and Livingston Manor. Tucked away on a mountain road, this is the perfect a place to relax and unwind. You can sleep. You can sip. You can cook. You can workout. You can hang. Outside of our doors you can fish. You can hike. You can stargaze. You can play. A place to do everything or nothing at all.

King Of The Hill

Romantic Mountain Top Retreat with Million Dollar Views Escape to this incredibly private, mountaintop vacation home, nestled on 80 acres of pristine land. Offering breathtaking, panoramic views. This peaceful retreat is the perfect getaway for relaxation and romance. Just 2 hours from the GW Bridge, enjoy the tranquility of nature without sacrificing modern comforts, including high-speed internet service. The ideal escape for those seeking both privacy and convenience.

A-Frame Chalet in the Heart of the Hudson Valley

Set back on a private road surrounded by tall trees, The Chalet is a three bedroom, three bathroom A-frame house in close proximity to all the main attractions of the Catskills and Hudson Valley. Perfect for a weekend getaway or an extended stay, and great for couples and families. The house has three levels, each with its own bedroom, bathroom and common area. Relax by the fire pit, sip morning coffee on the deck, read a book in the loft, or take a walk in the woods.

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

Unwind in this bright newly renovated 3BR/2BA retreat tucked away in tranquil Kerhonkson. Enjoy Ulster County's attractions or relax on the private deck overlooking breathtaking scenery— just 2 hours from NYC & minutes to Minnewaska & Mohonk. ✔ 3 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Deck (Seating, BBQ, Views) ✔ Office ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Laundry ✔ Free Parking The perfect escape for your upstate adventures!