House vacation rentals in Woodstock

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Family · Value · Walkability

Maple House: Private/Romantic Walk-to-Town Oasis

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.

Value · Family · Sleep quality

Stunning Light-filled Home w/HOT TUB walk to town

Standby for photos of our premium upgrades. Spotless home in walking distance to town. Featured in Hudson Valley Style magazine Road Affair's "15 Best Airbnbs in Woodstock" pick 2024. Explore Woodstock & nearby mountains from light-filled 1700 sq ft 1-BR home. Enjoy changing seasons from private patio w/hotub, dining, fire pit & grill 365 days a year. 1st floor fully equipped kitchen, 65" tv, dining room table & desk. 2nd floor bedroom is 800 sq ft & full bathroom & desk 2 dogs w/no fee

Family · Location · Bathroom

Broadview Retreat House, walk to town

"Broadview Retreat House" is located in Woodstock NY. The house is a 12 minute walk to Tinker Street, the center of town. Enjoy the peaceful mountain views . Great for families with kids. Easy Cancellation Policy. 4 large bedrooms and 2 full bathrooms. Large stocked kitchen. Detailed Host Guidebook with area restaurants, things to do. Contactless check in. Tons of extras included. Entire house to yourself. Vintage Airstream may occasionally house owners. *STR permit #21N-142 Town of Woodstock

Family · Location · Parking

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this quiet cabin perches on 18 acres with creek access, a vast forest & the greatest view in the county. 10 min to Woodstock. Seeking a vacation w friends or a romantic sojourn? Enjoy this rustic 2br 1ba cabin, cozy & spacious - a unique magical feel. Mega amenities incl the tub, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin's cabin called "Wonders Never Cease"

Family · Value · Accuracy

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Value · Family · Amenities

Fall Escape | EV | Hot Tub

The Maverick — A Mid-Century Escape Escape to The Maverick, a beautifully restored 1964 Mid-Century Modern retreat just 5 minutes from downtown Woodstock. Featured in Atomic Ranch and Country Home, this secluded design-forward hideaway blends iconic furnishings, soaring skylights, nature, and indoor-outdoor living. Relax on the expansive decks, explore nearby trails, or unwind in the new 7-person luxury spa hot tub beneath the stars. Come for the design, stay for the experience.

Value · Family · Outdoor spaces

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.

Location · Family · Comfort

Brookside, Walk to Town Center, Dog Friendly

Perfect Catskills basecamp! Three-bedroom getaway an 8-minute stroll to Woodstock’s shop and restaurants yet tucked beside a babbling brook. Why guests love it: • Bright living room with huge couch for cozy fireplace moments with friends and family • Ultra-fast Wi-Fi for work or play (3 desks) • Dog-friendly & fully stocked kitchen • Fire pit • Connected to nature As Superhosts we are committed to keeping the home spotless. Just press the reserve button and relax :)

Family · Location · Indoor spaces

Spacious, Private, Close to Town, Work From Home

Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated for a relaxing time in Woodstock, the home has an open and flowing layout. Conveniently located minutes from the center of town, it's perfect for those who want convenience to shopping and restaurants. A perfect home for a family getaway, work-from-home alternative or company retreat in the Catskills / Hudson Valley. Outdoor fire pit in the front yard!

Location · Family · Quiet

Modern Escape • Sauna • Firepit • Near Woodstock

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!

Family · Location · Accuracy

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.

Location · Family · Cleanliness