Family-friendly holiday 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.

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.

Woodstock Mountain Cottage w/ Pool /Swim

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for all of your tv needs! Located just 3 mins driving to the center of Woodstock. Swim in the pool, hike a nearby trail, enjoy nature, grill or relax in the hammock. Pool is shared with hosts. No guests of guests allowed and no parties.

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

Catskill Mtn Streamside Getaway - With EV Charger

Escape to this intimate one-bedroom Catskill cabin, nestled in a private yard with a trout stream at your doorstep. Just minutes from the charming town of Phoenicia, this retreat offers incredible hiking trails, three nearby ski resorts, and direct trout fishing access. Relax on the back porch with breathtaking views of snow-capped mountains or cozy up by the fireplace after a day of exploring. Perfect for couples or solo adventurers seeking peace and serenity.” EV Charger on site upon request.

Brand New Modern Cabin walk to town

This brand new cabin was built using green construction and features a living green roof. It is an open concept 1 bedroom with all new fixtures and a soaking tub. You can walk to town in approximately 10-12 minutes. This is in a neighborhood so there are visible neighbors but the architect utilized the natural surroundings to make it feel like you are in the woods. The beauty of this house is it’s access to town. If you look at my past reviews it’s the same location but a new house in front.

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.

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.

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Woodstock Charmer

Quirky 3 bedroom cottage built in 1927 and lovingly updated over the last 25 years. Only a few minutes from town, but hidden away in the woods with fabulous views of Overlook Mountain from our large deck. Perfect for 2 couples or a family with kids. We can accommodate 6 adults, but we only have one bathroom! Our home has a well stocked kitchen, lots of kids toys, games, books, TV and a record collection. There is AC in the master bedroom, fans in other rooms and a working fireplace.

The Carriage House: Garden Apartment

We offer a private apartment located on the first floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern decor and amenities, with more traditional countryside accents. The design, using the original carriage doors in the architecture, allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and even enjoy our grounds!

Jewel above the Pub with a view. Walk everywhere!

Spacious 2 bedroom apartment, above the historic Woodstock Pub! Roof deck with beautiful views of the Catskill mountains. Off street parking, on the bus route for Trailways Buses, as well, the local UCAT buses. $10 Off any food purchase with each booking, courtesy of your hosts. Join us for a pleasant stay in a beautiful town with so much to offer! Music, hiking, kayaking, biking, theatre, skiing, etc. Noise from pub fluctuates Friday/Saturday. Bar/restaurant closes 9pm.