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Holiday houses 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 $97 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    250 of Woodstock holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ 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 living and dining area features a combination of natural light and stylish furnishings. A warm wood dining table is surrounded by green chairs, while a cozy seating arrangement includes a leather couch and a unique wood slab coffee table. The space is enhanced by greenery from houseplants.
Home in Woodstock
4.96 out of 5 average rating, 136 reviews

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.

ValueLocationHospitality

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
4.99 out of 5 average rating, 158 reviews

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!

FamilyLocationNearby

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.
Guesthouse in Woodstock
5.0 out of 5 average rating, 458 reviews

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

FamilyLocationParks

Top Guest favourite
Cabin in Saugerties
4.99 out of 5 average rating, 216 reviews

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.

ValueLocationComfort

Top Guest favourite
A red house with yellow trim features a welcoming front porch and multiple windows. The porch is accessed by a set of steps and surrounded by a well-maintained yard with trees and shrubs, providing a charming entryway.
Cottage in Woodstock
4.85 out of 5 average rating, 302 reviews

Woodstock Dog Friendly Cozy Cottage in Town + Yard

Charming Country Escape – Pet-Friendly & Walk to Village Green! Enjoy country charm and modern comforts in this newly updated 2-bed, 1.5-bath home. Just 2.5 blocks from the Village Green, it’s the perfect getaway for city folk with dogs. Relax in the private backyard with waterfall sounds or stroll to shops, restaurants, and trails. Features include a cozy woodstove, updated kitchen & bath, queen beds, and a master bedroom with an en-suite plus a balcony. You and your pet will love it here!

LocationValueSleep quality

Guest favourite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock
4.97 out of 5 average rating, 184 reviews

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..

LocationFamilyComfort

Top Guest favourite
Home in Woodstock
4.98 out of 5 average rating, 147 reviews

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!

LocationFamilyBarbecue

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
4.86 out of 5 average rating, 271 reviews

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.

LocationValueCleanliness

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.
Apartment in Woodstock
4.89 out of 5 average rating, 484 reviews

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.

FamilyValueParking

Top Guest favourite
A spacious dining area is highlighted by a large wooden table surrounded by light-colored chairs. A cozy seating area with plush sofas is present. The room features wooden ceilings, vibrant orange drapes, and a fireplace, creating a welcoming environment filled with natural light.
Home in Woodstock
4.97 out of 5 average rating, 188 reviews

Woodstock Retreat -walk to town

An enchanting, comfortable home with elegant decor, this house is nestled in a rural wooded setting on 2 private acres. The house boasts 4 bedrooms with 5 beds (1 king and 4 queen) as well as 3 full baths. The 50 foot back deck contains comfortable seating, a shaded dining table with chairs, and a gas grill. And despite the peaceful seclusion of being set back from the road, it's only a 10 minute walk into town.

FamilyValueKitchen

Top Guest favourite
A unique three-story silo home is showcased, featuring a wooden exterior and numerous windows glowing warmly. Surrounded by snowy landscapes and trees, the structure is complemented by a wooden deck leading to an inviting red door.
Chalet in Willow
4.91 out of 5 average rating, 179 reviews

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

ValueLocationWi-Fi

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
4.98 out of 5 average rating, 256 reviews

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.

FamilyLocationBathroom

Popular amenities for Woodstock holiday rentals

KitchenWi-FiPoolFree 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
A modern kitchen features cabinetry in natural wood tones, complemented by a tile backsplash. Stainless steel appliances are visible, including a refrigerator, stove, and microwave. A dining table for two is set with wine glasses and simple place settings, while large windows provide ample natural light.
Cottage in Woodstock
4.96 out of 5 average rating, 232 reviews

Stunning Woodstock 1 BR Hideaway

ValueLocationQuiet

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
4.97 out of 5 average rating, 117 reviews

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

FamilyLocationDecor

Top Guest favourite
A peaceful outdoor space is presented, featuring a fire pit surrounded by seating chairs on a grassy area. A hammock is seen in the background, providing a cozy spot for relaxation amid lush greenery. The natural setting invites calmness and outdoor enjoyment.
Home in Woodstock
4.91 out of 5 average rating, 536 reviews

Brookside, Walk to Town Center, Dog Friendly

FamilyValueParking

Guest favourite
A bright and airy living room features large windows allowing natural light to fill the space. A stylish sectional sofa in warm tones is arranged on a patterned area rug, complemented by a coffee table. Skylights enhance the openness, while artwork decorates the walls.
Home in Woodstock
4.92 out of 5 average rating, 206 reviews

Fabulous Family House nr Woodstock Center

LocationFamilyWalkability

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
4.91 out of 5 average rating, 783 reviews

Dutch Touch Woodstock Cottage

LocationFamilyHeating

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
4.84 out of 5 average rating, 229 reviews

The Woodstock Barn Studio

LocationValueQuiet

Top Guest favourite
Home in Saugerties
4.96 out of 5 average rating, 283 reviews

Modern Escape • Sauna • Firepit • Near Woodstock

LocationValueAir conditioning

Guest favourite
Home in Woodstock
4.95 out of 5 average rating, 20 reviews

Woodstock Waterfall Hideaway · Walk To Tinker St!

LocationValueBathroom

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$335 AUD$337 AUD$325 AUD$333 AUD$354 AUD$351 AUD$358 AUD$364 AUD$347 AUD$375 AUD$362 AUD$346 AUD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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