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

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 stars1 week 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 stars1 week 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, 286 reviews

Chic Hudson Apartment - In the heart of Hudson, NY

DyeemahRating, 5 stars2 weeks ago
My family and I loved staying at Tj’s place in Hudson. The apartment was beautiful and exactly as described. Four of us stayed there for a week and we were very comfortable. Tj was very responsive when we had questions or issues (which we didn’t have many of since instructions were super clear). I also enjoyed the multiple yoga classes and spa sessions I participated in at their spa downstairs. The instructors and providers were all super friendly! The town of Hudson is incredible for anyone who loves to shop, look at art, and eat good food. It’s small, but there’s so much to see and eat! Everyone in town was genuinely friendly and welcoming. This was exactly what my family and I were hoping for for our vacation. We’re grateful we found Tj’s place!
Superhost
Apartment in New Paltz
4.87 out of 5 average rating, 289 reviews

Homey Haven:Inviting Airbnb Suite with kitchen

ElanaRating, 5 stars4 days ago
Nichole was kind enough to accommodate us on very short notice, and the space was exactly what we needed - comfortable, clean, and right near the town center, too. (Despite what some other people have commented, the mattress was actually perfect for me!) Would definitely stay here 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 Newburgh
4.86 out of 5 average rating, 150 reviews

#1, Historic Studio, Newburgh, Beacon, West Point

GerardoRating, 5 stars5 months ago
They were super hospitable, friendly, and gave great recommendations for spots nearby.
Guest favorite
Apartment in Hudson
4.9 out of 5 average rating, 167 reviews

Private 1BR Apartment 1 Block from Warren St.

JamieRating, 5 stars2 weeks 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.

Other great vacation rentals in Woodstock

Guest favorite
Home in Windham
5 out of 5 average rating, 22 reviews

Cozy Mountain Cabin Near Windham Slopes

MardaRating, 5 stars2 weeks ago
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!
Guest favorite
Chalet in Hunter
4.98 out of 5 average rating, 153 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

CarmenRating, 5 stars2 weeks ago
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.
Guest favorite
Home in Hensonville
5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 stars2 months 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.
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 stars2 months 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 stars3 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 stars1 month 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, 28 reviews

Luxury Spacious Private Home w/tub! Enjoy Spring

SantiagoRating, 5 stars2 months 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.
Superhost
Chalet in Fleischmanns
4.73 out of 5 average rating, 158 reviews

Sauna equipped Belleayre Cozy Cabin

ChloeRating, 5 stars2 months ago
Perfect for a ski weekend. Sauna is great, and location cannot be beat.

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 apartment rentals in Woodstock?

    Experience the best of Woodstock with our apartment rentals, starting at about $70 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.

  • 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.

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