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.
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
Cabin in Kingston
4.99 out of 5 average rating, 336 reviewsCome Stay in "The Shoe"
Cabin in Boiceville
5.0 out of 5 average rating, 128 reviewsCome enjoy our wee cabin!
Loft in woodstock
4.88 out of 5 average rating, 114 reviewsPeace & Quiet & Space (!) in Woodstock
Guest suite in Woodstock
4.94 out of 5 average rating, 318 reviewsPerfect Woodstock Location- Short Walk to Town
Place to stay in Woodstock
4.88 out of 5 average rating, 299 reviewsWoodstock Cabin 3 Miles from Town
Cottage in Saugerties
4.97 out of 5 average rating, 131 reviewsCozy Cottage, just off exit 20, 1/2 hr to Hunter
Guesthouse in Woodstock
5.0 out of 5 average rating, 303 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Cabin in Saugerties
4.95 out of 5 average rating, 171 reviewsCozy Cottage for Two
Other great vacation rentals in Woodstock
Home in Catskill
4.96 out of 5 average rating, 139 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Cabin in Tannersville
4.99 out of 5 average rating, 148 reviewsCabin by the woods, Hunter Mountain & Kaaterskills
Home in Mount Tremper
4.96 out of 5 average rating, 217 reviewsOverlook Creek Cottage 1 Near Phoenicia
Cottage in Bearsville
4.99 out of 5 average rating, 143 reviewsColdbrook Cottage
Bungalow in Saugerties
4.88 out of 5 average rating, 194 reviewsSaugerties Cottage with Creek Access
Cottage in Phoenicia
4.91 out of 5 average rating, 580 reviewsRomantic Getaway: Lovingly Restored Esopus Cottage
Cottage in Kerhonkson
4.91 out of 5 average rating, 386 reviewsHome Alone Woods
Cottage in Saugerties
4.93 out of 5 average rating, 221 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Quick stats about vacation rentals in Woodstock
Total rentals
270 properties
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
120 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
32K reviews
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
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 160 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Woodstock?
Four-legged friends are welcome in Woodstock. Choose from more than 120 vacation rentals for guests traveling with pets.
How much does it cost to stay in cabin rentals in Woodstock?
Experience the best of Woodstock with our cabin rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Woodstock vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Woodstock, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Woodstock have self check-in?
Absolutely! We offer over 80 house rentals with self check-in in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodstock have a gym?
Absolutely! We offer over 10 house rentals with a gym in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Woodstock have a bbq area?
Absolutely! We offer over 20 cottage rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cabin rentals in Woodstock?
Woodstock has more than 10 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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