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

Pet-friendly vacation rentals in Woodstock

Guest favorite
Home in Saugerties
4.87 out of 5 average rating, 126 reviews

Le Petit Cottage - French Country in Saugerties

SwetaRating, 5 stars1 month ago
This cottage was even better than the pictures! Such great details and charm - plenty of space and cozy at the same time. Wood-burning stove perfect for the winter. Fully stocked kitchen, comfortable bedrooms and spacious bathrooms. Location was convenient and very close to Saugerties. Super responsive and helpful host as well. Would highly recommend!
Guest favorite
Cabin in Woodstock
4.97 out of 5 average rating, 147 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

TammyRating, 5 stars4 months ago
I loved staying in this home and hope to rent it again. It is just a few minutes from town and nestled in the woods. The place is beautifully decorated and has everything you need.
Superhost
Cottage in Kerhonkson
4.91 out of 5 average rating, 181 reviews

*spring-ready* Pet-friendly private cabin!

MatthewRating, 5 stars2 weeks ago
Great place! We really had a lovely time and our dog loved every minute of it. I would highly recommend Darla’s place to anyone who wanted a weekend escape from New York City. The nature, the hiking, the food - it was all wonderful
Top guest favorite
Bungalow in Hurleyville
5 out of 5 average rating, 130 reviews

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

SilissaRating, 5 stars1 week ago
Cozy, clean, and packed with extra-special touches. The house is spotless, with a cozy fireplace for cold weather—and a fire pit outside for warmer days. The bathroom and kitchen have everything you need and more, including snacks and ingredients to make homemade waffles or oatmeal with a ton of toppings to choose from. The bed is very comfortable (definitely not always the case in an AirBnB). The hosts are so kind and responsive. I will 100% be staying again!
Top guest favorite
Cabin in Jefferson
5 out of 5 average rating, 478 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

TinaRating, 5 stars2 weeks ago
A gem of a cabin! Snug, warm, next to a creek, beautiful fields to walk - a special place of heaven.
Top guest favorite
Cabin in New Paltz
4.97 out of 5 average rating, 151 reviews

New Paltz dog friendly retreat w/salt water POOL

PaulRating, 5 stars5 months ago
Excellent stay for a small group - we only stayed for a weekend, but would be a perfect spot for a weeklong trip as well.
Superhost
Home in West Kill
4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

TatyanaRating, 5 stars2 months ago
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.
Guest favorite
Cabin in Hunter
4.95 out of 5 average rating, 154 reviews

Log Cabin with view Ski Slopes in Hunter Mountain

SimonaRating, 5 stars3 weeks ago
Great spot just a couple minutes from Hunter base. Well equipped, everything you need. My kids especially appreciated the winter-themed stuffed animals!! They're already asking to go back.

Other great vacation rentals in Woodstock

Guest favorite
Home in Windham
5 out of 5 average rating, 21 reviews

Cozy Mountain Cabin Near Windham Slopes

JulesRating, 5 stars3 months ago
Great stay. Would come back next year to enjoy new years at Windham!
Guest favorite
Home in Hensonville
5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 stars1 month ago
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.
Apartment in Ravena
4.67 out of 5 average rating, 3 reviews

Mountain Getaway 2BR duplex apt

NatashaRating, 5 stars20 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
Home in Tannersville
4.97 out of 5 average rating, 75 reviews

CottageintheClouds-InVillage 3BR 2BA, King bed

JeffreyRating, 5 stars2 months 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 Hunter Mountain, Hunter
4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

PaulRating, 5 stars1 month ago
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.
Top guest favorite
Home in Athens
5 out of 5 average rating, 16 reviews

Lake house with arcade games

AdrienneRating, 5 stars2 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favorite
Cabin in Shandaken
4.99 out of 5 average rating, 104 reviews

A Place Called Home in The Catskill

KateRating, 5 stars3 weeks ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Guest favorite
Home in Tannersville
4.93 out of 5 average rating, 27 reviews

Luxury Spacious Private Home w/tub! Enjoy Spring

SantiagoRating, 5 stars1 month ago
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.

Quick stats about vacation rentals in Woodstock

  • Total rentals

    220 properties

  • Total number of reviews

    28K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    100 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

  • Are there vacation rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 140 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 100 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 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.

  • 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 40 cabin rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Woodstock have wifi?

    Absolutely! We offer over 20 apartment 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 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cottage Rentals in Woodstock?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with self check-in, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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