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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.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

Sauna, Jacuzzi, Swim Hole. Fully fenced yard good for dogs! The 1822 Lewis Cottage of Lewis Hollow - Old Woodstock, Pre-Columbian Indian Kairns. Deed reads, "This property starts at the ancient stone heap between Gradus Lewis and Peter Livingston's farm." (DESC Robert) If interested in booking dates over Christmas, any holiday (or ANY DATES that appear booked) PLEASE reach out and inquire. We look to ACCOMMODATE ALL to the best of our ability. *No checkins are avail Tgiving or x-mas days

Brand New Modern Cabin walk to town

This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town. If you look at my past reviews it’s the same location but a new house in front.

Timberwall Ranger Station | Your Upstate Base Camp

The Timberwall Ranger Station is the perfect home base for your peaceful upstate escape. Located minutes from Woodstock, Saugerties, and Kingston, this breathtaking hand-built cabin is close to all the Catskills and Hudson River Valley have to offer. The cabin is a restful place year-round: for enjoying spring birdsong at breakfast; swaying away an afternoon in a breezy summer hammock; starry skies and luscious wines around an autumn campfire; a cozy winter morning amidst freshly fallen snow.

Uptown kid/dog friendly home w yard tennis & park

Sunny Colonial Uptown Across from Park | Dog-Friendly | Family-Ready Bright, airy, and perfect for exploring Kingston and the Hudson Valley. This home is designed for comfort, fun, and relaxation. Step outside and you’re across from park with trails, playground, petting zoo, tennis courts, and a dog park—something for everyone. Whether you’re planning a family or romantic getaway, weekend with friends, or a pet-friendly escape, this home has every comfort and a prime and walkable location.

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Charming Artist Cottage

We welcome couples, solo adventurers, families and small dogs (sorry, no cats) to our year round cabin. Two BDRs (1 Q off LR1, 1 F off DR 1/2 wall w/privacy curtain, no door), full kitchen, screened-in porch, large LR with a stone fireplace, satellite internet & TV. Enjoy nature and a peaceful setting at the foot of Overlook Mt. on 6 wooded acres with a brook. Privacy, and 3 miles to Woodstock Village. Original art work from our grandfather Joseph Garlock adds to the charm of our cabin.

Spring Upstate Cabin

Beautiful 2 bedroom/1 bath home centrally located between Woodstock and Saugerties in the gorgeous Catskill Mountains. Come for hiking, skiing, shopping and dining, it is all at your fingertips! Your home is a chic cabin situated on a large property and provides a fully stocked kitchen if you choose to cook at home, a gas grill, and fire pit in the back yard for evening enjoyment. Visit the many fun shops just down the road, or one of our lovely locally owned restaurants! Enjoy!

Luxury+firepit+stream+walk/town=Brook Cottage Too

Brook Cottage Too occupies the west wing of a newly-renovated 1928 Woodstock artist’s cottage featuring: oversize north-light windows; skylights; 1 bedroom w/king bed; spa-like bathroom; newly-remodeled kitchen; fire stove; bluestone patio w/gas grill + firepit; AC. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream + conservation land. Immaculately clean + available for long-term rentals, as well as short-term stays.

Chic and eclectic retreat at Woodstock/Saugerties!

Step into a meticulously renovated 1810 barn boasting chic, modern, and eclectic design, nestled amidst landscaped lawns and gardens. Experience light-filled spaces ideal for a comfortable and convenient stay in upstate New York. Perfect for year-round adventures with nearby picturesque hikes, trails, swimming holes, and ski slopes. Conveniently located to explore Woodstock and Saugerties' vibrant art, music, wellness spas, and culinary delights.