Woodstock vacation rentals

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Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Colony153 locals recommend
Bearsville Theater195 locals recommend
Garden Cafe Woodstock234 locals recommend
Bread Alone Bakery204 locals recommend
SILVIA275 locals recommend
The Woodstock Inn on the Millstream4 locals recommend

Other great vacation rentals in Woodstock

Other great vacation rentals in Woodstock

Guest favorite

Cottage in Saugerties

4.98 out of 5 average rating, 126 reviews

Cozy Cottage, just off exit 20, 1/2 hr to Hunter

Jun 9 – 16

G$27,273 GYD per night
Guest favorite

Tiny home in Kingston

4.9 out of 5 average rating, 164 reviews

Esopus Creek modern Tiny house Retreat!

Dec 14 – 21

G$33,016 GYD per night
Guest favorite

Guesthouse in Woodstock

5.0 out of 5 average rating, 297 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

Jan 26 – Feb 2

G$51,545 GYD per night
Superhost

Guest suite in Woodstock

4.83 out of 5 average rating, 452 reviews

The Carriage House: Garden Apartment

Aug 1 – 8

G$38,267 GYD per night
Superhost

Farm stay in High Falls

4.87 out of 5 average rating, 804 reviews

Dave's Milk Barn

Mar 27 – Apr 3

G$30,535 GYD per night
Guest favorite

Guesthouse in Mount Tremper

4.91 out of 5 average rating, 322 reviews

Cozy Catskill Cottage Perfect Getaway for Two

May 18 – 25

G$30,408 GYD per night
Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 110 reviews

Spacious, Private, Close to Town, Work From Home

Oct 25 – Nov 1

G$92,458 GYD per night
Superhost

Tiny home in Saugerties

4.95 out of 5 average rating, 312 reviews

Cozy Cabin on the Farm

May 3 – 10

G$32,582 GYD per night

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.

  • 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!

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

    Experience the best of Woodstock with our guesthouse rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Absolutely! We offer over 40 cabin 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 cabin rentals in Woodstock have a bbq area?

    Absolutely! We offer over 50 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 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 House Rentals in Woodstock?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 80 homes with self check-in, over 110 homes with a bbq area, over 130 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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