Woodstock vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Woodstock
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodstock vacation rentals
Other great vacation rentals in Woodstock
Home in Windham
5 out of 5 average rating, 20 reviewsCozy Cabin Near Windham Mountain
Chalet in Hunter
4.98 out of 5 average rating, 142 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Home in Hensonville
5 out of 5 average rating, 8 reviewsPerfect Windham & Hunter Ski House 2 Miles to Mntn
Home in Windham
5 out of 5 average rating, 15 reviewsLuxurious Home & Amazing Views
Home in Tannersville
4.97 out of 5 average rating, 73 reviewsCottageintheClouds-InVillage 3BR 2BA, King bed
Home in Athens
5 out of 5 average rating, 14 reviewsLake house with arcade games
Cabin in Shandaken
4.99 out of 5 average rating, 103 reviewsA Place Called Home in The Catskill
Home in Tannersville
4.92 out of 5 average rating, 24 reviewsBeautiful Home in the Woods - Hot Tub - Ski Nearby
Quick stats about vacation rentals in Woodstock
Total rentals
250 properties
Total number of reviews
29K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
160 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
- Hudson Valley Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Long Island Vacation rentals
- The Hamptons Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- South Jersey Vacation rentals
- Cape Cod Vacation rentals
- Montreal Vacation rentals
- Rentals with a patio Woodstock
- Family-friendly rentals Woodstock
- Rentals with a hot tub Woodstock
- Rentals with breakfast Woodstock
- Rentals with a washer and dryer Woodstock
- Apartment rentals Woodstock
- Rentals with an EV charger Woodstock
- Rentals with a fireplace Woodstock
- Fitness-friendly rentals Woodstock
- Rentals with outdoor seating Woodstock
- Rentals with a fire pit Woodstock
- Kid-friendly rentals Woodstock
- Cottage rentals Woodstock
- House rentals Woodstock
- Pet-friendly rentals Woodstock
- Waterfront rentals Woodstock
- Monthly Rentals Woodstock
- Rentals with pools Woodstock
- Cabin rentals Woodstock
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes