
Vacation rentals in Woodstock
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Top-rated vacation rentals in Woodstock
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Popular amenities for Woodstock vacation rentals
Woodstock house rentals

Hillside Views in Hudson Valley

Broadview Retreat House, walk to town

Tinker Street Retreat • Rustic Echoes & Sound

Whispering Pines: Secluded Retreat near town

Hot tub with stunning views, 5 min to Woodstock

Eagle Rock House

Woodstock Catskill Escape: Bright Views & Private

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View
Woodstock cottage rentals

Charming creekside cottage in Phoenicia

Direct streamside with private stream access

New:Cozy Barn-Style Retreat Minutes From Woodstock

Carriage House on Falls, Walk to Village

Magnolia Cottage

Cozy Catskill Cottage on the Pantherkill

Sun Cottage- "A view with a room(s)."

Catskills Getaway w/AC on 3 Acres near Woodstock
Other great vacation rentals in Woodstock

Winston's Place - Woodland Cozy Catskills Cabin

Cozy Catskills Cabin

Willow Treehouse - secluded, unique, romantic

Gorgeous Tiny House with Mountain View

Lenny Bee's Bee Happy AirBnB

Woodstock Charmer

Mt. Guardian Guest House Exquisite Mountain Views

Stylish and Cozy Mountain Retreat
Quick stats about vacation rentals in Woodstock
Total rentals
230 properties
Total number of reviews
29K reviews
Family-friendly rentals
130 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
150 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
What types of vacation rentals are available in Woodstock?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Woodstock. From over 110 house rentals to over 20 cottage rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 150 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 110 vacation rentals for guests traveling with pets.
Are there Woodstock vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Woodstock, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Woodstock?
Experience the best of Woodstock with our cottage 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.
Do cottage rentals in Woodstock have self check-in?
Absolutely! We offer over 10 cottage 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 20 house rentals with a gym in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Woodstock have a bbq area?
Absolutely! We offer over 40 cabin rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Woodstock have wifi?
Absolutely! We offer over 10 cabin rentals with wifi 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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- Hunter Mountain
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Belleayre Mountain Ski Center
- Thunder Ridge Ski Area
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Norman Rockwell Museum
- Windham Mountain
- Villa Roma Ski Resort
- Taconic State Park
- Mohawk Mountain Ski Area
- Plattekill Mountain
- Beartown State Forest
- Hunter Mountain Resort