Family-friendly holiday rentals in Woodstock

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.

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

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

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.

The Woodstock Barn Studio

Once a Woodstock chicken barn, your space is the lower level which has been renovated as a studio apt. that maintains its rustic charm with wide plank pine floors & ceiling beams. Only 2 blocks (a ten minute walk) to down town Woodstock & the NYC bus stop. We are 1 block from the Tinker St. Cinema and about 1.5 miles from the Bearsville theater. There are hiking trails for you to enjoy, the beautiful Wilson State Park as well as The stunning views of Cooper Lake and the Ashokan Reservoir.

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.

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.

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!

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.

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.

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.

Cozy Silo Home with Mountain Views near Woodstock

Escape to the Willow Silo, a unique 3-story tower retreat with stunning mountain views. Comfortably sleeping 6, this charming home is nestled in the woods yet just 10 mins from Woodstock & 15 from Phoenicia. Features include an indoor fireplace, outdoor fire pit, and a deck perfect for stargazing. Your ultimate relaxation getaway awaits, surrounded by hiking trails and nature's beauty. PERMIT No: 23N-277