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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

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

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.

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Retro-Chic Cabin in Woodstock - Sauna

Perfect upstate escape! Whether you're planning a romantic couples getaway, a fun trip with friends, a family vacation, or even a much-needed solo escape, The Retro Chic House offers the ideal stay for a memorable local Upstate Experience. This stunning renovated property is designed to cater to a variety of preferences and is guaranteed to provide you with an unforgettable stay. Located 8 mins to Woodstock, 12 mins to Saugerties, & picturesque drive to Hunter!

Cozy forest luxury cabin

This winter enjoy the falling snow in your own private forest at the Maverick. As featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCentury deck home furnished with Eames and other iconic era furnishings. The Maverick is secluded yet just 5 minutes from downtown Woodstock as well as beautiful hiking, running, and biking trails. The home is perfectly set up for indoor | outdoor entertainment & dining.

Woodstock Family Home w/ Tree House + Heated Pool

Town of Woodstock Special Use (aka STR) Permit #23-0683. Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor.

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.

Architect's Farmhouse in Woodstock

This rustic and cozy farmhouse is the perfect retreat from the city. Just a few minutes from the heart of Woodstock, the property feels secluded, quiet, and deeply relaxing. It’s a great spot for anyone looking for a true country farmhouse experience. This is a magical Woodstock retreat filled with rustic charm, eclectic furnishings, and modern comforts. A perfect place for families, groups, and anyone looking for a peaceful country escape.

The Woodstock Suite

Welcome to The Woodstock Suite! It’s the perfect retreat for those seeking a peaceful getaway in the heart of nature, just minutes from the center of America's most famous small town—Woodstock, New York. The Suite is located in a lovely residential neighborhood on a quiet tree-lined street. Bright & airy during the day and comfortable & cozy at night, this newly renovated space is designed with your tranquility in mind.