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Holiday rentals in Woodstock

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Quick stats about holiday rentals in Woodstock

  • Total holiday rentals

    Explore 250 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 31,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    250 of Woodstock holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties

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!

4.99 out of 5 average rating, 159 reviews
Top guest favourite
A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.
Guest house 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

5.0 out of 5 average rating, 463 reviews
Guest favourite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home 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.

4.94 out of 5 average rating, 398 reviews
Guest favourite
An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.
Home in Woodstock

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

4.99 out of 5 average rating, 279 reviews
Top guest favourite
The cabin is set amidst lush greenery, featuring a screened porch illuminated by warm lights. Two lounge chairs are positioned on the manicured lawn, with the structure's blue exterior complemented by large windows reflecting the soft hues of sunset.
Cabin in Woodstock

The Pike Lane Cabin & Nature Preserve

The Pike Lane Cabin is nestled in the woods on 7 acres but walking distance to the center of Woodstock. This private retreat offers 2 sleeping areas. The oversized master has a queen bed and its own living area with a queen size sofa bed. The other sleeping area is a full pullout sleeper in the main room. Fully equiped kitchen, full bath, linens, TV, wifi, AC. Four adults allowed plus children 12 or under. Arriving in town early? Come enjoy the grounds or lay in a hammock while you wait until 3.

4.9 out of 5 average rating, 658 reviews
Top guest favourite
A light-filled living area features an open concept with a spacious gray sofa adorned with decorative pillows and an orange accent couch. A wooden coffee table occupies the center, while a kitchen with modern appliances is visible in the background. Green plants and framed artwork enhance the inviting space.
Home in Woodstock

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

4.97 out of 5 average rating, 118 reviews
Top guest favourite
Cabin in Woodstock

Pet Friendly Cabin Doh-Ray in Woodstock

Experience the serenity of the woods and still be close to town. We're on the side of Mt. Guardian just 5 minutes from The Cub Market & 10 minutes from the Village Green. Hike up to the viewpoint from the front door, take a leisurely walk at Cooper Lake, take a dip at a local swimming hole, or just relax on the porch and watch the wildlife stroll by. Visit a cool restaurant in town or in Kingston or just grill & watch a movie with our surround sound system. Bring your pets!

4.98 out of 5 average rating, 168 reviews
Top guest favourite
A charming cottage exterior is framed by lush greenery. The entrance is marked by a fenced patio area with a gravel path leading to the door. Potted plants add a touch of greenery, while a shaded seating area with a fire pit invites relaxation.
Cottage in Woodstock

Luxury+firepit+stream+walk/town=Brook Cottage Too

Brook Cottage Too occupies the west wing of a newly-renovated 1928 Woodstock artist’s cottage featuring: oversize north-light windows; skylights; 1 bedroom w/king bed; spa-like bathroom; newly-remodeled kitchen; fire stove; bluestone patio w/gas grill + firepit; AC. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream + conservation land. Immaculately clean + available for long-term rentals, as well as short-term stays.

4.99 out of 5 average rating, 205 reviews
Top guest favourite
Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

4.98 out of 5 average rating, 239 reviews
Top guest favourite
Home in Woodstock

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!

4.98 out of 5 average rating, 147 reviews
Guest favourite
The cabin's exterior is characterized by natural wood siding and large glass panels that integrate the structure with its wooded surroundings. A private courtyard with outdoor seating is visible, along with lush greenery and carefully placed stones that enhance the natural landscape.
Cabin in Woodstock

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. The distance is .5 mile. ( half mile)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.

4.86 out of 5 average rating, 273 reviews
Guest favourite
A well-lit entryway features wooden stairs leading up to a hallway. Light-colored walls and warm wooden flooring create a welcoming atmosphere. A decorative runner rug lies on the steps, and light fixtures above enhance visibility. Doorways at the top of the stairs lead to additional spaces.
Flat in 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.

4.89 out of 5 average rating, 488 reviews

Popular amenities for Woodstock holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Woodstock's top sights

Bearsville Theater

246 locals recommend

Colony

223 locals recommend

Sunfrost Farms

183 locals recommend

Catskill Mountain Pizza

128 locals recommend

Shindig

122 locals recommend

Mower's Saturday Sunday Flea Market

74 locals recommend

Other great holiday rentals in Woodstock

Top guest favourite
The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.
Home in Woodstock

Dutch Touch Woodstock Cottage

4.91 out of 5 average rating, 784 reviews
Top guest favourite
The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.
Treehouse in Willow

Willow Treehouse - secluded, unique, romantic

4.96 out of 5 average rating, 875 reviews
Guest favourite
A cozy sleeping area features warm wooden paneling and a spacious bed topped with a striped blanket. A colorful, patterned cushion adds a pop of color. Framed artwork is displayed on the walls, with a warm glow from wall sconces illuminating the space.
Guest house in Woodstock

Rocket Room - Rock Stars Only

4.87 out of 5 average rating, 1042 reviews
Top guest favourite
Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

4.99 out of 5 average rating, 220 reviews
Top guest favourite
A living room features a leather sofa and a wooden coffee table, surrounded by colorful artwork on the walls. Natural light fills the space through two windows, revealing a warm wood ceiling. A rocking chair and patterned rug add comfort to the inviting atmosphere.
Home in Woodstock

Sweeping mountain views in Woodstock, NY

4.98 out of 5 average rating, 256 reviews
Top guest favourite
The exterior of the barn studio displays a rustic green facade, featuring a prominent gabled window above a set of double doors. A gravel path leads to a grassy yard adorned with potted plants and garden chairs, creating an inviting outdoor space.
Barn in Woodstock

The Woodstock Barn Studio

4.85 out of 5 average rating, 233 reviews
Guest favourite
Home in Woodstock

Woodstock Waterfall Hideaway · Walk To Tinker St!

4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Woodstock

Waterfall Location | Walk to Town

5.0 out of 5 average rating, 10 reviews

When is the best time to visit Woodstock?

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Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Stays near the village center connect guests to shops, galleries, and live music, while areas surrounded by woods invite a quieter retreat. Both settings are frequently suggested for enjoying Woodstock’s character.

  • What are the best things to do in Woodstock with kids?

    Explore nature trails at Comeau Property, visit local playgrounds, or get creative during community art activities. Seasonal festivals often include family-friendly performances and hands-on workshops.

  • What are some of the best things to do in Woodstock?

    Explore local art galleries, stroll through village shops, and hike scenic trails near the area. Music performances, seasonal farmers’ markets, and craft studios offer more ways to connect with Woodstock’s creative spirit.

  • How is the weather in Woodstock?

    Woodstock experiences cold, snowy winters near 16–35°F (-9–1°C), warming to pleasant spring and summer days around 46–82°F (8–28°C). Autumn brings cooler temperatures and colorful foliage, which draws many visitors.

  • When is the best time to visit Woodstock?

    Late spring to early autumn is often recommended for milder weather, vibrant foliage, and seasonal outdoor events. Many travelers also enjoy winter’s quieter atmosphere and opportunities for snowshoeing.

  • What are the best places to visit in Woodstock?

    The Woodstock Artists Association & Museum, Bearsville Theater, and local farmers’ markets are frequently suggested. Walking the village green and discovering artisan shops are also popular activities.

  • What are some hiking trails in Woodstock?

    Woodstock has several popular hiking options, including trails at Overlook Mountain and Comeau Property. These paths invite exploration through forested landscapes and hilltop views.

  • What are some family activities we can do in Woodstock?

    Families can enjoy creekside walks at Comeau Property, browse children’s sections in independent bookstores, or take part in weekend art workshops. Parks and picnic areas around the village invite relaxed outings.

  • What are some of the best day trip ideas from Woodstock?

    Popular day trips include exploring Catskill Mountain hiking areas, historic towns with antiques and galleries, or riverside parks for picnics and walks. Nearby waterfalls and farms invite further discovery around the region.

  • Are there any pet friendly accommodations available in Woodstock?

    Many stays in Woodstock welcome pets, especially around the village center and near wooded areas. Look for properties with private yards or easy access to green spaces for comfort and convenience.

  • What are some local tips for visiting Woodstock?

    Arriving early on weekends helps with parking and access to market stalls. Many galleries, music spaces, and shops feature changing exhibits—drop in often to discover new artists and performers.

  • What is Woodstock known for?

    Woodstock is widely recognized for its artistic community, music heritage, and countercultural history. The town continues to draw creatives and those seeking a blend of arts, nature, and local food.

  • What are the best hidden gems to explore in Woodstock?

    Seek out independent galleries, tucked-away sculpture gardens, or creekside paths not far from the village. Some cafes double as music venues or showcase rotating art by local creators.

  • What are the best foods to try in Woodstock?

    Woodstock is known for farm-to-table dining, local cheeses, and fresh baked goods. Vegetarian and vegan cuisine, as well as international flavors, are frequently suggested in its restaurants and markets.

  • What should I bring for a trip to Woodstock?

    Pack layers for shifting temperatures, sturdy shoes for walking, and a light rain jacket, as weather can vary with the seasons. Bringing a reusable water bottle and a day pack supports both hikes and village strolls.

  • What is the nightlife in Woodstock like?

    Nightlife in Woodstock centers on live music venues, locally owned bars, and intimate performance spaces. Visitors can find acoustic sets, open mics, and art events in a welcoming, creative atmosphere.

  • What are the most popular events or festivals in Woodstock?

    Woodstock has several well-known festivals, such as the Woodstock Film Festival in autumn and music gatherings during the summer. Art fairs and makers’ markets frequently attract visitors throughout the year.

  • Are there family friendly vacation rentals in Woodstock?

    Woodstock has a range of family-friendly stays, including homes with multiple bedrooms, outdoor space, and easy access to parks. Many properties are set up with amenities for children and group gatherings.

Destinations to explore