Woodstock vacation rentals

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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

Other great vacation rentals in Woodstock

Guest favorite
A spacious cabin exterior is showcased, featuring a large balcony and an inviting wooden deck. The landscape is lightly covered in snow, while the surrounding trees indicate a serene, natural environment. A stack of firewood is neatly arranged beside the entrance.

Home in Windham

5 out of 5 average rating, 20 reviews

Cozy Mountain Cabin Near Windham Slopes

LeshchevRating, 5 stars1 month ago
Fantastic home, fantastic stay. We had a blast and our kids had a blast. Conveniently close to the slopes. Perfect place to experience all the winter fun!
Guest favorite
A snow-covered house is surrounded by trees blanketed in white snow. The structure features a sloped roof and large windows, partially obscured by snow. A stone chimney is visible, and a thick layer of snow covers the ground, creating a serene winter landscape.

Home in Hensonville

5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 starstoday
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.
Superhost
The spacious kitchen features wooden cabinets and stainless steel appliances, with a breakfast bar and a dining table for four. A comfortable seating area is highlighted by a plush sectional sofa, complemented by decorative cushions and an indoor plant. Natural light filters through the windows.

Apartment in Ravena

4.67 out of 5 average rating, 3 reviews

Mountain Getaway 2BR duplex apt

NatashaRating, 5 stars18 months ago
Vitaliy's home was beautiful!! It was the perfect getaway that we were looking for! Very quiet area & our surroundings were picturesque! We even saw a deer & its baby eating & playing in the backyard!! The inside of the home was very spacious & well decorated! The bed was very comfy also! The pictures posted in the listing were exactly what we encountered! I would definitely come back here again!! Thank Vitaliy for your hospitality, it was very much appreciated!
Guest favorite
The living area features two large sofas in a floral pattern, complemented by a cozy armchair and small table. A flat-screen TV is mounted on the wall. A dining area is visible in the background, leading into a well-equipped kitchen.

Home in Tannersville

4.97 out of 5 average rating, 74 reviews

CottageintheClouds-InVillage 3BR 2BA, King bed

JeffreyRating, 5 stars2 weeks ago
We came for a weekend skiing at Hunter and Donna's place was perfect... Location in the town of Tannersville was great, we could walk down to the restaurants/shops in town. Less than a 10 minute drive to the slopes at Hunter. Everything in the home was as described and just what we needed - from the kitchen to the bedrooms to the living space. And Donna was super flexible and responsive as we had a few questions leading up to our stay.
Guest favorite

Home in Athens

5 out of 5 average rating, 15 reviews

Lake house with arcade games

AdrienneRating, 5 stars3 weeks ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favorite
A spacious cabin is nestled among trees adorned with autumn foliage. The wooden structure features a combination of log and stone design, with a welcoming front porch and double garage. A paved driveway leads up to the entrance, highlighting a serene natural setting.

Cabin in Shandaken

4.99 out of 5 average rating, 103 reviews

A Place Called Home in The Catskill

AliciaRating, 5 stars1 month ago
We really enjoyed our stay. We had three families and the space accommodated us well. John’s place is well located to Bellayre - 15 min away. The kitchen and layout were great and the house is very comfortable. I definitely recommend it and would stay again. Thanks for a great stay!!
Guest favorite
A modern home is nestled among snow-covered trees, showcasing a spacious front porch and large windows reflecting the winter sky. The driveway is lined with fresh snow, leading to a clear view of the surrounding landscape and serene atmosphere.

Home in Tannersville

4.92 out of 5 average rating, 26 reviews

Luxurious Spacious Private Home w/tub - Come Ski!

RebeccaRating, 5 stars2 weeks ago
The house is amazing! It is even more gorgeous than the pictures. And Svetlana was an amazing host. Super communicative and answered all our questions and more. 10/10 stay
Superhost
A tranquil winter scene is captured from a deck, showcasing a snow-covered landscape. A wooden bench sits beside a small, frozen pond, surrounded by frosted trees and shrubs. Snow blankets the railing, creating a serene and peaceful atmosphere.

Chalet in Fleischmanns

4.74 out of 5 average rating, 156 reviews

Sauna equipped Belleayre Cozy Cabin

AlexRating, 5 stars1 month ago
Great place. A bit cold in the winter so the fireplace comes in handy. Grill makes for convenient cooking. very private feel. The sauna is great and very personal!

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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