House holiday rentals in Woodstock

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.

Air conditioned.Walk to Village Green.Pets welcome

• Ideal location • 8-minute walk to town center • Air Conditioned • Private 1/2 acre of land • Up to 2 pets welcome • 5 beds (3 queens, 2 singles) • Walkable to most restaurants and shops • Peaceful outdoor setting • Firepit • Creekside location with bridge in backyard • Serene and clean with soft sheets and fluffy towels • Cozy, peaceful atmosphere • Fireplace inside • Fire pit outside • Charcoal BBQ • Two TVs • Dedicated work space, 3 desks • Excellent Wifi • 40 mins to Hunter or Belleayre

Romance+history+luxury+privacy in town=Maple House

Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located on a quiet dead-end lane just 1 block from the Woodstock Village Green ~ the heart of this famous “colony of the arts”. You can walk to restaurants, cafes, galleries, boutiques, theaters, clubs... Or you can stay home and relax in your private oasis of peace and beauty with a fully-fenced landscaped backyard, fireplace, chef’s kitchen, heated soaking tub, and luxury amenities.

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

Grandma's Place an Easy Walk to Woodstock

Simply decorated and conveniently located, Grandma's Place is on a quiet road just minutes from all Woodstock has to offer. Vintage furnishings make this popular rental a fun place to stay. The house shares a roof with Grandma's Apartment but the spaces are separated with a secure and sound proofed door. The only shared areas include the driveway and garden. If you wish to rent only one bedroom, please see link at Grandma's Place - Queen Only and send an inquiry about your desired dates.

Fabulous Family House nr Woodstock Center

Our gorgeous newly decorated Woodstock abode is the perfect destination for a family vacation. Ideally located in town, walking distance to Woodstock center and the legendary Levon Helms Studios. 15 mins to HITS. Close to hiking, swimming & biking. A fully equipped kitchen, new Weber grill, wood-burning fireplace + plenty of wood & space for everyone. Bring to the end a perfect day upstate day by grilling or playing one of our multiple games inc corn hole, darts, scrabble etc.

Serene Retreat w/ Cedar Hot Tub & Fire Pit

Whether you’re planning a couples getaway, a trip with friends, a family vacation, or even a solo escape, The Woodstock Retreat is your home away from home in the Catskills. Located just 5 mins from Woodstock, 10 mins from Saugerties, and surrounded by endless dining, shopping, and outdoor activities. Two separate bungalows, a handmade cedar hot tub, fire pit w/ Adirondack chairs, and hammocks are just a few of the features that make The Woodstock Retreat special.

Mid Century Oasis

Escape the oppressive heat and retreat to the cool forest which surround 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.

Chic historic house 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.