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Woodstock vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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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

Woodstock apartment rentals

Guest favorite
Apartment in Poughkeepsie
4.94 out of 5 average rating, 342 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

ChristineRating, 5 stars4 days ago
We absolutely loved staying here! The home is so cozy and had so many nice touches. Highly recommend, and will definitely be back!
Top guest favorite
Apartment in Hudson
4.93 out of 5 average rating, 316 reviews

Park View Apartment in the Heart of Hudson

CatherineRating, 5 stars4 days ago
I love staying on Warren when I am in Hudson! Such great people & shops. The location is at the far end of the street, but still extremely walkable. I stayed here during a weekend visit with my son at Bard College, which is about 30 minutes away. Perfect space for the two of us, with a nice big kitchen if you want to cook. Parking is metered in front of the building, but we didn't have a problem finding spots nearby that weren't. It is a second floor apartment that overlooks the park. Nice little place, highly recommend!
Guest favorite
Apartment in Hudson
4.93 out of 5 average rating, 285 reviews

Chic Hudson Apartment - In the heart of Hudson, NY

PhillipRating, 5 stars3 months ago
This place is fabulous! I was looking for a place for a long weekend retreat and was delighted to find this listing. The apartment is large, well appointed, and very clean. Below is a gorgeous spa/yoga center, where I treated myself to two treatments over the long weekend. All around are great restaurants and shops. I didn’t get in my car once after parking because I just wanted to soak up the serenity of this apartment, the spa below, and the historic street in Hudson. I envision returning with my husband, with friends, and alone for another personal retreat. Thank you for such a great stay!
Superhost
Apartment in New Paltz
4.87 out of 5 average rating, 287 reviews

Homey Haven:Inviting Airbnb Suite with kitchen

CherylRating, 5 stars1 month ago
I’ve stayed at Nichole’s place many times. It’s clean and comfortable and convenient for me. Will stay again.
Guest favorite
Apartment in Poughkeepsie
4.86 out of 5 average rating, 105 reviews

Your Own Pied-a-Terre "WALKWAY OVER THE HUDSON"#2

AubreyRating, 5 stars6 months ago
We had an excellent stay! Tania was so nice and made us feel right at home, and responded to all messages and inquiries quickly. The apartment was very clean and had plenty of space. Highly recommend staying here!
Guest favorite
Apartment in Hudson
4.9 out of 5 average rating, 167 reviews

Private 1BR Apartment 1 Block from Warren St.

JamieRating, 5 stars1 week ago
My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!
Guest favorite
Apartment in Hudson
4.95 out of 5 average rating, 204 reviews

Newly Renovated Apt. Mins from Warren St.

JackRating, 5 stars2 months ago
The apartment was very cozy and homey, plus very clean. It's perfect for a weekend getaway in Hudson. Great access to all the best restaurants and shops that Hudson has to offer.
Top guest favorite
Apartment in Hudson
4.97 out of 5 average rating, 278 reviews

Thomas Jenkins Guesthouse hudson

EvanRating, 5 stars3 months ago
My girlfriend and I loved staying at Fabrice's place! He was an excellent host with prompt communication. Great location. Very clean and beautiful furniture. Comfortable bed. Everything we could have asked for and would highly recommend.

Pet-friendly vacation rentals in Woodstock

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

Le Petit Cottage - French Country in Saugerties

SwetaRating, 5 stars2 months 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!
Superhost
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Superhost
Cottage in Kerhonkson
4.91 out of 5 average rating, 182 reviews

*spring-ready* Pet-friendly private cabin!

KyleRating, 5 stars2 weeks ago
Darla’s cottage was such a sweet spot for a weekend getaway. Super cozy, clean, and peaceful—exactly what we were looking for. It felt tucked away in the woods but still really easy to get to, and just a few minutes down the road from Rough Cut Brewing, which was a big plus. We loved being able to grab some beers, then come back and relax inside. Darla was a great host—friendly, but gave us plenty of space. Would totally stay again next time we’re in the area!
Superhost
Bungalow in Hurleyville
5 out of 5 average rating, 133 reviews

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

CameronRating, 5 stars5 days ago
Just under an hour from the Catskills, this comfortable and cozy listing was just right for a short weekend trip for local hiking. My partner and I would argue that this is the nicest Airbnb we’ve stayed at. There is a wonderful bagel breakfast place to the south. We’ll definitely be back in the future!
Superhost
Cabin in New Paltz
4.97 out of 5 average rating, 151 reviews

New Paltz dog friendly retreat w/salt water POOL

PaulRating, 5 stars6 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 stars3 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.
Superhost
Cottage in Cornwallville
4.93 out of 5 average rating, 112 reviews

Cozy Catskills Reteat with Geothermal Heat

JoelleRating, 5 stars2 weeks ago
We had a wonderful stay at Niall's! It was perfect for our needs. The house was clean and cozy. Niall was friendly and helpful!
Superhost
Cabin in Hunter
4.95 out of 5 average rating, 154 reviews

Log Cabin with view Ski Slopes in Hunter Mountain

SimonaRating, 5 stars1 month 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.

Pet-friendly apartment rentals Woodstock

Top guest favorite
Apartment in Roxbury
4.94 out of 5 average rating, 283 reviews

"Your Country Getaway at Beulah Land Farm."

HenryRating, 5 stars3 days ago
We really enjoyed our stay at Your Country Getaway at Beulah Land Farm. The 2nd floor apartment was very clean, comfortable and spacious. The bed was great - slept very well. Plenty of towels, pillows, linens, toiletries and books. Plenty of free parking space. Safe and bucolic countryside location in the Catskill Mountain region. The hostess met us on arrival to make sure everything was okay. We would definitely consider staying here again.
Guest favorite
Apartment in Tivoli
4.85 out of 5 average rating, 221 reviews

Ground Floor Apartment on Hudson River

MarisolRating, 5 stars4 months ago
Lugar accesible a restaurantes. Fue una escapada corta para ver nuestro hijo en BARD College, justo lo que necesitabamos.
Top guest favorite
Apartment in Coxsackie
4.97 out of 5 average rating, 145 reviews

Susie's Climax Creations

frederickRating, 5 stars1 month ago
Susie’s warmth & hospitality are unmatched. We must protect her at all costs. She is the best, and her farm stay is an absolute dream. Do not hesitate for a moment regarding staying here. Book it and enjoy a respite from the craziness of the world.
Top guest favorite
Apartment in Acra
4.99 out of 5 average rating, 157 reviews

Burnt Knob Mountain Escape

MatthewRating, 5 stars2 months ago
Theresa was an amazing host, she clearly communicated with us along the way, and made sure we had our privacy & provided the upmost comfort. Her space was well kept and full of considerate touches to facilitate a relaxing stay, the subtleties go a long way. We enjoyed the hot tub in the snow, shared a few stories of skiing adventures & loved the friendly visits from Ben. The views were picturesque to boot, we definitely plan to come stay in other seasons.
Guest favorite
Apartment in New Paltz
4.97 out of 5 average rating, 135 reviews

An Adorable Getaway in the Gunks!

SaraRating, 5 stars6 months ago
We loved our stay at this cozy spot just a quick drive out of downtown new paltz. Perfect launching spot for hikes or the town and ideal for a morning coffee on the patio. Angela was responsive and accommodating.
Superhost
Apartment in Kingston
4.82 out of 5 average rating, 108 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars4 months ago
Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.
Superhost
Apartment in Rhinebeck
4.76 out of 5 average rating, 206 reviews

Rhinebeck Village Apartment

JillRating, 5 stars1 month ago
Vicky’s charming Airbnb is a perfect getaway! The space is attractively decorated with thoughtful touches that make it feel warm and inviting. The kitchen is impressively well-stocked, making it easy to cook and enjoy meals at home. The bed is super comfy, ensuring a restful night’s sleep. Best of all, the location is ideal—just a short walk to the charming village of Rhinebeck, where you’ll find great shops, restaurants, and cafes. Highly recommend!
Guest favorite
Apartment in New Paltz
4.9 out of 5 average rating, 132 reviews

Enthusiastic Spirits. Close to Parks W/Cliff Views

RakeshRating, 5 stars5 months ago
Great place with lovely views!!! Beds were very comfy. I felt very refreshed after sleeping which I rarely feel at hotels/ airbnbs. Carl was very friendly and passionate about hospitality.

Quick stats about vacation rentals in Woodstock

  • Total rentals

    230 properties

  • Total number of reviews

    29K reviews

  • Family-friendly rentals

    140 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

  • 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.

  • 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 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!

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

    Absolutely! We offer over 70 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 20 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 10 cottage 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 cottage rentals in Woodstock?

    Woodstock has more than 10 family-friendly cottage 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 30 homes with self check-in, over 10 homes with wifi, over 50 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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