Woodstock vacation rentals

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Top-rated vacation rentals in Woodstock

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

Guest favorite
A cozy living area is displayed with warm wooden walls and a plush sofa adorned with vibrant pillows. A small green side table complements the space. A wood stove is positioned nearby, with a window allowing natural light to illuminate the area.

Cabin in Bovina Center

4.97 out of 5 average rating, 388 reviews

Delightful Cabin with Extras

Come to beautiful Delaware County and settle into serene and comfortable surroundings for a restorative getaway in any season at this lovely Bovina cabin. Enjoy the hot tub, wrap-around deck, firepit, and pristine pond on 8 acres of rolling hillside property. *Notes: While our Air BnB Plus photo shoot was taken in winter, the cabin is a fantastic year-round respite, beautiful in every season. Also - each adult beyond 2 is $25 per night, but we do not charge for children, so do not include kids in your guest # (but let us know). Inside this 2- bdrm Catskills cabin, you'll find an open living/kitchen space with comfy couches and wood stove. Outside, there's a wrap-around deck with grill and hot tub. The cabin sits mountainside on eight beautiful acres of meadows, forest, a fantastic swimming pond and a fire pit. Swimming pond, deck, grill, fire pit, outdoor hot tub, wi-fi, and great local dining and festivals. Nearby farm stands, hiking, skiing, fishing, golf, tennis, and low-key town pool (in Andes). Amazing beef cattle are just down the road, so if you'd like some for the grill, we can put it in the fridge! We live right up the road so are readily available to answer all of your questions and provide whatever we can to make your stay memorable. The cabin is on Bramley Mountain in the beautiful town of Bovina Center. Neighboring farms offer organic veggies, grass-fed meat, cheese, and milk. The town also has top-rated Catskill dining, including Brushland Eating House, Table on Ten, and the Mountain Brook Inn. We're three hours from NYC by car. A beautiful ride! Buses also run regularly from Port Authority to nearby Andes or Delhi, so if you don't have a car, we're happy to pick you up. Fully equipped kitchen, 2 bedrooms (1 queen bed and 1 full bed), blow-up bed, games, books, DVDs and video streaming access.

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Family I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Whether you're traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Guest favorite
A spacious house showcases a modern design with large windows and a welcoming façade. A full deck with red chairs overlooks the surrounding landscape, while colorful autumn trees add warmth to the serene setting.

Home in Round Top

4.96 out of 5 average rating, 191 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Guest favorite
A wooden chair is positioned on a spacious deck, offering a view of the serene lake and surrounding greenery. A kayak is visible on the grass nearby, with the calm water reflecting the lush landscape.

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite
A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

4.92 out of 5 average rating, 462 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Guest favorite
A cozy living area features a plush sofa and a circular area rug with a nature-inspired design. A coffee table sits centrally, and large sliding doors provide access to the balcony. Natural light flows in, creating a relaxed atmosphere.

Condo in Windham

4.89 out of 5 average rating, 176 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Guest favorite

Townhouse in Hunter

4.92 out of 5 average rating, 71 reviews

Stunning Mountain View Catskill Vacation Escape

Enjoy the BEST LOCATION IN THE CATSKILLS with Scribner's Lodge right next door, Hunter Mountain 1 mile away, Tannersville a town over, Windham mountain 7 miles away, hiking, lakes, restaurants and breweries all around! Amazing 4 bedroom, 3 bathroom townhome with unbeatable views of Hunter Mountain. Stocked with all the essentials, multiple fireplaces, outdoor grill and a new patio! Bring your skis and snowshoes or rent skates for the winter and enjoy the shared outdoor pool in the summer.

Guest favorite
An outdoor deck features a hot tub surrounded by wooden flooring. Comfortable seating is arranged nearby, with decorative cushions adding color. Scenic mountain views and a serene lake are visible in the background, framed by autumn foliage under a clear blue sky.

Home in Windham

4.96 out of 5 average rating, 23 reviews

“Amazing Mtn & Ski Slope Views “

The highest breathtaking Mtn Views in Windham w ski slope and lake views. This amazing resort like atmosphere includes a 8 person hot tub w 5 acres of tranquility ,3 outdoor firepits , walking pathways through beautiful gardens with a ski lift chair and Adirondack chairs at fire pits also a Japanese style garden with serene lake & Mtn views as well as from every room in the home. Two fireplaces and a lg bar w game rm as well as 2 living rooms w tvs. A 4 min drive to town & 6 min to slopes.

Guest favorite

Cottage in Livingston Manor

4.99 out of 5 average rating, 136 reviews

Cozy mountain top home - views, 5acres & a gym.

Located 2hrs from NYC, 7mins from Livingston Manor and close to Belleayre and Plattekill ski mountains. Sat atop a mountain, with 5 acres that sweep away from the property revealing stunning long distance views. Beautiful light throughout - front room with fireplace, full renovated kitchen, lounge, dining area, master bedroom, 1 large guest room, office / single bedroom, 2 bathrooms and huge covered back porch + a full home gym complete with Peloton bike, Peloton tread + ping pong table.

Guest favorite
A log cabin is illuminated under a starry sky, surrounded by lush greenery. Two adirondack chairs are positioned around a small table in the foreground, creating an inviting space to relax. The cabin features a spacious deck with multiple seating areas, visible through large glass doors.

Cabin in Hunter

4.99 out of 5 average rating, 184 reviews

Lakeside log cabin with Mtn views (dog friendly)

Tranquil log cabin on lake 10 min from Windham & Hunter Mtns (dog friendly). If you're searching for a peaceful, dog friendly, Catskill Mtn getaway, then look no more! From the moment you enter this charming waterfront log cabin you'll sense it's Zen vibes. The cabin is tastefully decorated with an open floor plan which includes a wood burning stove, Lg kitchen, Lg bathroom with X-Lg sky lit shower, 1 Lg bedroom with Queen size bed looking onto a covered porch and breathtaking views!

Guest favorite
An outdoor deck is shown, featuring wooden flooring and a black railing. Lush green trees and a grassy area create a serene backdrop, while a clear blue sky is visible above. A white chair is positioned on the deck, inviting relaxation.

Condo in Hunter

4.89 out of 5 average rating, 84 reviews

Cozy Slope Side Retreat

Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Guest favorite
A wooden deck features a large outdoor dining table surrounded by black chairs, with an umbrella providing shade. A grill is visible in the background, and lush greenery surrounds the space. The geodome structure is prominently displayed to one side.

Dome in Monticello

4.96 out of 5 average rating, 25 reviews

007 Geodome

Looking for a vacation that will really stand out from the rest? Look no further! With a unique 007-themed interior, this geodome vacation rental with 1 bathroom is sure to make lasting memories. You can even bring your dogs along! Shred the slopes of Holiday Ski and Fun Park, just 9 miles away, or visit Bethel Woods. Kick back in the cozy interior, have an al fresco meal on the grill, or simply enjoy time with your loved ones. Book now! *Please note this is a non-smoking unit.

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Cucina297 locals recommend
SILVIA275 locals recommend
Garden Cafe Woodstock234 locals recommend
Red Onion225 locals recommend
Bread Alone Bakery203 locals recommend
Sunflower Natural Foods Market201 locals recommend

Quick stats about vacation rentals in Woodstock

  • Total rentals

    230 properties

  • Total number of reviews

    29K reviews

  • Family-friendly rentals

    140 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

Your guide to Woodstock

Welcome to Woodstock

Despite the fact that the 1969 Woodstock Festival took place a 90-minute drive to the southwest at Bethel Woods Center for the Arts, the town of Woodstock is the exact cross-section of arts and nature that you’d expect from its association with the famous music fest. Sitting in the foothills of the Catskills, the arts colony was established here in 1902, drawing artists of all types — ranging from craftspeople and photographers to actors and musicians. Free-spirited creativity has a certain kind of purity here, inspired by the vast forests, peaks, and waters — in fact, the Ashokan Reservoir is so crisp that it supplies 40 percent of New York City’s drinking water.


The best time to stay in a vacation rental in Woodstock

Woodstock is at its best in the summer months with comfortable temperatures from day to night, though a burst of summer rain isn’t unusual. Events are also in full swing, such as the Maverick Festival, with chamber music from June to September; Mower’s Saturday Market flea market and the Woodstock Farm Festival from May through the fall; and the Woodstock-New Paltz Arts & Craft Show, with a spring edition in May and fall one in September. Summer is also prime time to book one of the area’s house rentals and revel in the greenery with outdoor activities such as hiking and biking. Autumn brings its own delights with stunning fall colors, especially around the second week of October. While snow tends to blanket the area in the coldest months, the Catskills’ winter sports offerings can’t be topped. As the snow melts away, spring brings back the tourists, as the temperature works its way up to its comfy zone.


Top things to do in Woodstock

Overlook Mountain Wild Forest

While most mountain hikes lure visitors with their sprawling mountaintop views, Overlook Mountain (with the Hudson River Valley in the foreground and five states in the distance) does that and so much more. Along the way up the Spur Trail, you’ll find the ruins of the never-finished Overlook Mountain House. At the summit, an impressive fire tower reaches 3,140 feet high. Also worth a visit: The Karma Triyana Dharmachakra Tibetan Buddhist monastery across the street from the trailhead.

The Center for Photography at Woodstock

What started as an artists’ colony’s urge to give photographers their own space has grown into a gallery and workshop center that both showcases and supports photography in every kind of light.

Opus 40

Just a 10-minute drive to the east in Saugerties is a 6.5-acre earthwork sculpture that was hand-shaped from bluestone by artist Harvey Fite over the course of 37 years. Sitting on 50 acres of meadows, forest, and quarries, the site — often likened to Stonehenge — also hosts theatrical and musical performances.

Frequently Asked Questions

  • How much does it cost to stay in private suite rentals in Woodstock?

    Experience the best of Woodstock with our private suite rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 80 house rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Woodstock house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Woodstock, available on Airbnb. Make a splash and soak up the sun in style!

  • Do cabin rentals in Woodstock have self check-in?

    Absolutely! We offer over 30 cabin rentals with self check-in in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly cottage rentals in Woodstock?

    Four-legged friends are welcome in Woodstock. Choose from more than 10 cottage rentals for guests traveling with pets.

  • Do house rentals in Woodstock have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodstock have a bbq area?

    Absolutely! We offer over 110 house rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Woodstock have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Woodstock?

    Woodstock has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Woodstock?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 50 homes with a bbq area, over 30 homes with self check-in, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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