Family-friendly holiday rentals in Woodstock

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1 1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Kitchen · Family · Parks

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.

Indoor spaces · Kitchen · Walkability

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

Kitchen · Family · Checkout

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!

Family · Kitchen · View

Away Upstate, a cozy retreat w/ Firepit

The Away Upstate retreat is nestled in the breathtaking Catskills and is your perfect home away from home year-round. Whether you’re planning a couples getaway, a trip with friends, a family vacation, or a solo escape, our retreat is a perfect place to create lasting memories. Share stories around the outdoor firepit, cozy up by the woodstove or read a book on the hammock. Located: 5 mins from Woodstock 10 mins from Saugerties 15 mins from Kingston 30 mins from Hunter Mtn. @awayupstate

Family · Kitchen · Backyard

Hudson Valley Evergreen Treehouse

Welcome to our new Scandinavian designed 5 bedroom, 3 bath treehouse in the Hudson Valley. Experience a relaxing nature setting w/mountain view, 6 min. drive to downtown Woodstock, launchpad to Hunter, Belleayre, nearby wineries & hiking trails. The house offers a private setting, borders a nature preserve, & features a chef's kitchen, living room w/fireplace, cathedral ceilings, wrap around deck, screened in porch, new jacuzzi spa, large movie room, pool table, ping pong table, & more.

Indoor spaces · Family · Comfort

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.

Family · Indoor spaces · Hot tub

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!

Family · Indoor spaces · Sleep quality

Hidden Pines - Downtown Woodstock by Millstream!

Two blocks from Downtown Woodstock tucked away on a quiet lane sits Hidden Pines, a classic Woodstock Cottage. No need for a car here! Spacious light filled rooms and a bluestone terrace provide a soothing respite. Stroll down for a swim at the Millstream which is 1/2 block away. This cottage has been lovingly renovated and includes Central AC and heat. Please note this is a guest house. The main house is quietly owner occupied with its own private separate side yard.

Indoor spaces · Kitchen · Wi-Fi

Woodstock Historic Artist Estate - The Carriage House

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. Today the former carriage house of the picturesque estate is an architect-renovated gem in an idyllic setting bordering a public preserve, a short walking distance to the center of Woodstock.

Family · Kitchen · Getting around

Nook above the Pub!

1-bedroom, above the historic Woodstock Pub. Full Futon, able to accommodate 3 people. On local and Trailways Bus lines. Walk to shops, restaurants & The Colony. Plenty of hiking trails, skiing, kayaking, music, theatre, etc. Noise from pub below on weekends fluctuates. Bar/restaurant last seating at 9pm Fri/Sat. $10 food voucher, courtesy of your hosts. Twin mattress available on request for extra guest. $25 fee.

Kitchen · Indoor spaces · Long stay

Sweeping mountain views in Woodstock, NY

A quick 3 minute drive to the center of town, our recently built 3 bedroom house has gorgeous mountain views and is on 5 beautiful secluded acres surrounded by trees. The property is fantastic in all seasons and close to amazing Catskill skiing, hikes, waterfalls, swimming holes, and the Hudson River, as well as the towns of Phoenicia, Saugerties, Kingston, Catskill, Hudson, Rhinebeck, and Tivoli.

Indoor spaces · Family · Bathroom