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Woodstock vacation rentals

We found 737 vacation rentals — enter your dates for availability

Discover a selection of 68 homes, 13 apartments, and other vacation rentals in Woodstock that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Woodstock

Showing deals for:Nov 7 - Nov 14

Image gallery for Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

Outdoor dining
10 out of 10 rating
Exceptional
(5 reviews)

Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

Saugerties, NY

13% off
Price is $479
$3,356 for 7 nights
All fees included
Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

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Find out more about Woodstock

Find out more about Woodstock

Why visit Woodstock

  1. Outdoor adventures: Experience hiking, biking, and exploring nature preserves amidst stunning landscapes.
  2. Artistic charm: Discover a vibrant arts scene with local galleries, crafts, and cultural events.
  3. Historic sites: Visit historic colleges and universities that reflect Woodstock's rich heritage.
  4. Family-friendly activities: Enjoy various attractions suitable for all ages, making it perfect for families.
  5. Cozy accommodations: Stay in charming vacation rentals, including cabins and cottages that offer local charm.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? You're in for a treat! Discover a variety of vacation rentals, including charming private homes, cozy cabins, and inviting cottages. Whether you’re searching for Woodstock house rentals or friendly rentals that cater to your needs, we’ve got you covered. Explore the best options for your stay and enjoy the perfect blend of comfort and local charm in this beautiful destination.

  • Houses: The top choice for visitors to Woodstock, these homes offer spacious accommodations ideal for families, friends, or couples.
  • Cabins: A close second, cabins provide a rustic escape for those seeking adventure in nature.
  • Cottages: These charming retreats are perfect for a cozy and intimate getaway.
  • Apartments: A convenient option for travelers looking for modern amenities in a central location.
  • Chalets: A unique choice, chalets blend comfort with a touch of mountain style.**

Top attractions near Woodstock

Woodstock, New York, is a fantastic destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and a rich cultural experience. Popular attractions include nature preserves, historic colleges and universities, and beautiful waterfalls. Whether you're looking to explore the great outdoors or enjoy family-friendly activities, Woodstock has something for everyone, making it a perfect getaway for travelers seeking both adventure and culture.

  1. Bethel Woods Museum: Located 3 miles from Woodstock, this museum offers a rich cultural experience, showcasing the history of the 1969 Woodstock Festival and the evolution of music and art in America.
  2. Bard College: Situated 11 miles away, Bard College is an esteemed historic institution with beautiful architecture and vibrant arts programs, providing a glimpse into academia and culture.
  3. Opus 40: Just 4 miles from Woodstock, this unique sculpture garden features impressive stoneworks and outdoor installations, perfect for family exploration and enjoying nature.

Things to do recommended for couples

For a romantic getaway in Woodstock, explore the thrilling slopes at Hunter Mountain, unwind at the serene Copperhood Retreat & Spa, or embark on an adventurous ride on the H Ski Lift. Each experience offers a unique blend of excitement and relaxation perfect for couples.

Things to do recommended for families

Your family vacation in Woodstock, New York, can include a relaxing day at Saugerties Village Beach, just 9 miles away, or enjoy sports at Dietz Stadium, also 9 miles away. For some ice skating fun, head to Kiwanis Ice Arena, conveniently located 9 miles from Woodstock.

What do I need to keep in mind when booking a vacation in Woodstock

When planning your trip, whether you're traveling with friends, family, pets, or looking for extended stays, be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily narrow down your options for all these preferences and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, being close to family-friendly attractions is worth considering.
  • Taking your pets with you to Woodstock: For many families, a vacation just isn’t the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Woodstock

Woodstock, New York, offers a delightful blend of outdoor adventures and artistic charm. Nestled in the scenic Hudson Valley, this vibrant town invites visitors to explore its relaxing atmosphere, rich history, and family-friendly activities. Just a short drive away, nearby cities enhance the experience with friendly locals and urban vibes. Whether you're hiking in the mountains or enjoying local art, Woodstock promises a refreshing getaway filled with unforgettable moments.

  • Kingston: Located 10 miles from Woodstock, Kingston is a vibrant city rich in history and outdoor adventure. Nestled along the banks of the Hudson River, it offers ample opportunities for skiing at nearby resorts, as well as hiking and exploring the scenic mountains and beautiful lakes. The historic downtown area is charming, with unique shops, restaurants, and cultural venues. Notably, visitors can explore the local landmark of Kingston's historic college university, adding an educational aspect to your travel experience.
  • Saugerties: Just 9 miles away from Woodstock, Saugerties is another gem for outdoor enthusiasts. This city is surrounded by stunning natural landscapes, including mountains and lakes, making it a prime location for skiing, hiking, and other outdoor activities. The local stadium often hosts events, adding to the vibrant community atmosphere. Saugerties invites travelers to enjoy its quaint shops and eateries while immersing themselves in the adventurous spirit of the Hudson Valley.
  • Zena: Zena is a charming village located within the Woodstock area. It is known for its breathtaking scenery and outdoor experiences, making it a perfect spot for hikers and nature lovers. With ski fields nearby, visitors can enjoy both winter sports and summer hikes that showcase the village’s stunning mountains and lakes. Zena offers a peaceful escape with its historic places that reflect the rich culture of the region, allowing travelers to connect with the beauty and serenity of the Hudson Valley.

Best time to go to Woodstock

If you're planning a trip to Woodstock, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.0°F (-3.9°C)Light RainMostly SunnySlightly LowSlightly High
February26.6°F (-3.0°C)Light RainMostly CloudyAverageSlightly High
March34.5°F (1.4°C)Light RainMostly SunnyAverageSlightly Low
April46.2°F (7.9°C)Light RainMostly SunnyAverageSlightly Low
May57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighAverage
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighAverage
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighSlightly Low
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, booking an extended stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash™ on the total booking amount. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or review and manage your travel arrangements. You can easily access properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore and utilize Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Enjoy the natural beauty of a Woodstock house for rent

This mountain town shares the name with an iconic music festival, and still embraces the peaceful bohemian atmosphere. Innovative live music performed at Bearsville Theater and Levon Helm Studios keeps the festival's spirit alive. Throughout the area, you can stop in boutique shops selling tie-dye T-shirts and New Age jewelry. The Elena Zang Gallery and several others around town showcase the works of local artists. As with all rental houses in the Catskills, Woodstock's lodgings accentuate the area's natural beauty. The vaulted ceilings and tall windows allow the sunlight in and give you a view of the outdoors

 

Activities and attractions in and around Woodstock

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Woodstock a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (11.1 mi / 17.8 km)
  • Woodstock Music Shop (0.1 mi / 0.1 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Mohonk Golf Course (18.1 mi / 29.2 km)
  • Windham Mountain Resort (19.2 mi / 30.9 km)
  • Woodstock Golf Club (0.5 mi / 0.8 km)

Adventure abounds in Woodstock

The Catskill Mountains provide a wealth of hiking trails to explore, whether you prefer to take a gentle saunter or to tackle something more challenging. The trail up to Kaaterskill Falls is one of the easiest, but the 1.7-mile-long round trip takes you past spectacular falls—the highest 2-step waterfall in the state. Head up to Hunter Mountain for an exciting day out. In the winter, you can enjoy skiing and snowboarding across 58 trails, and during the summer you can enjoy an adrenaline-pumping zipline adventure, or traverse the hills in a thrilling 4x4 tour.

Woodstock—a year-round destination

If you want to take advantage of the nearby skiing and snowboarding, Woodstock vacation rentals are perfect in winter, when temperatures drop to as low as 13 degrees and the area experiences the most snowfall. If you prefer to explore the great outdoors in warmer weather, June through August is one of the best times to visit, with temperatures of around 65-70 degrees. The shoulder seasons also provide pleasant conditions for enjoying the outdoor pursuits on offer. May through September enjoy mild conditions, with the mercury hovering around the 60-degree mark.

Awe-inspiring vistas await in Woodstock

You never have to stray far from Woodstock vacation rentals to enjoy the wealth of hiking provided by the Catskill Mountains. Gorgeous areas like Bluestone Wild Forest and Indian Head Wilderness are home to fantastic trails and bouldering, and also boast breathtaking falls—the sight of which will make even the most challenging hike well worth the effort. Water lovers will enjoy the area, too. The Ashokan Reservoir and Hudson River are both close by, and there are also numerous watering holes for swimming, such as the picturesque Millstream.

How to get to and around Woodstock

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.2 mi (43.7 km) from the city center.

Frequently asked questions

How much does it cost to rent a vacation home in Woodstock?
Prices for vacation rentals in Woodstock vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woodstock to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woodstock vacation house rentals?
You can find great discounts on house rentals in Woodstock on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Woodstock ski resort rentals?
For ski resort rentals near Woodstock, New York, travelers should consider the nearby Hunter Mountain area, which is a popular destination for skiing and snowboarding. The village of Hunter offers a variety of accommodations, including cozy lodges and rental homes that cater to families and groups. Many of these properties feature ski-in/ski-out access, which is a significant advantage for those looking to maximize their time on the slopes. Expect amenities such as fireplaces for warming up after a day on the mountain, hot tubs for relaxation, and fully equipped kitchens for convenient meal preparation.

In addition to Hunter, the area around Phoenicia and Mount Tremper also provides options for vacation rentals. Here, you can find rustic cabins and charming cottages that often come with spacious decks, stunning views of the surrounding mountains, and proximity to local hiking trails. These properties may include amenities like wood-burning stoves, outdoor grills, and comfortable living areas superb for gathering after a day of skiing or exploring the Catskills.

Visitors to the Woodstock area can also enjoy the vibrant arts scene and local dining options, making it an excellent choice for those who want a blend of outdoor adventure and cultural experiences.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular rental option, with approximately 57 available throughout the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups. Many also come with outdoor spaces, such as decks or gardens, where guests can relax and enjoy the natural beauty of the Catskills. Additionally, there are around 17 cottages, alongside several apartments, cabins, and chalets, which provide unique and cozy alternatives for travelers.
Are there any family house rentals in Woodstock?
In Woodstock, New York, there are some available family-friendly house rentals, with around 69 options to choose from. This charming town, located in the Catskill Mountains, offers a variety of accommodations superb for families. Many of these homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can enjoy nature.

Visitors can explore the nearby Woodstock town center, known for its artsy vibe, vibrant shops, and vibrant music scene. Additionally, the area is close to beautiful hiking trails in the surrounding mountains, providing ample opportunities for outdoor adventures. Families can also take advantage of amenities like Wi-Fi and air conditioning, ensuring a comfortable stay while enjoying all that this picturesque locale has to offer. See all family-friendly rentals in Woodstock.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, there are several vacation homes available for rent that feature pools and hot tubs, with around 26 options to consider. This picturesque town in the Catskills is known for its artistic vibe and natural beauty, making it a superb getaway. Many of these rentals come with amenities that enhance the vacation experience, including private pools, relaxing hot tubs, spacious outdoor decks, and fully equipped kitchens, which are ideal for both relaxation and entertaining.

Travelers can choose homes that are set amidst the serene woods or near the charming town center, providing easy access to local shops, galleries, and restaurants. Additionally, many properties offer cozy living spaces with fireplaces, superb for unwinding after a day of exploring the scenic trails and vibrant arts scene in the area. Find your rental in Woodstock with a pool or a hot tub.
Can I find long-stay vacation rentals in Woodstock?
A long-stay vacation rental in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, there are numerous pet-friendly house rentals available, offering a variety of amenities that cater to both travelers and their furry companions. Many properties in the area come equipped with essential features such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Some rentals even include private yards, making it easier for pets to roam freely.

The town is known for its vibrant arts scene and stunning natural surroundings, with nearby hiking trails and parks that welcome pets. The picturesque Catskill Mountains provide plenty of opportunities for outdoor adventures, including hiking and exploring nature with pets. Additionally, the area is home to pet-friendly cafes and shops, allowing travelers to enjoy the local scene without leaving their pets behind. See all pet-friendly rentals in Woodstock.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, New York, there are numerous remote work vacation rentals available, with around 82 options to choose from. This charming town, known for its artistic vibe and natural beauty, provides a conducive environment for remote work. Many of these properties are equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable office setups, including desks and ergonomic chairs. Some rentals even feature additional conveniences like computer monitors and safes for securing valuables.

Travelers can expect to find a variety of accommodations, from cozy cabins to spacious homes, often set amidst picturesque surroundings that inspire creativity and relaxation. The town is also close to outdoor attractions, including hiking trails and the scenic Catskill Mountains, providing opportunities for refreshing breaks during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodstock vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodstock with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Woodstock?
In Woodstock, vacation rentals typically offer a variety of popular amenities that enhance the stay for travelers. Most properties come equipped with WiFi, making it easy for guests to stay connected while enjoying the serene surroundings. Kitchens are a common feature, allowing visitors to prepare their own meals, often complete with essentials like blenders and coffee or tea makers for added convenience. Many rentals also include outdoor spaces such as decks or patios, great for relaxing and taking in the picturesque views of the Catskills.
When is the best time to visit Woodstock for a vacation rental?
July marks the height of the travel season in Woodstock, attracting visitors eager to immerse themselves in the vibrant arts and music scene that the town is famous for. This lively month sets the stage for numerous festivals, outdoor concerts, and bustling farmers' markets, making it the superb time for those seeking a dynamic experience filled with local culture.

During the summer months, particularly from July to September, travelers can enjoy warm temperatures averaging in the mid-70s to low 80s Fahrenheit. This pleasant climate is ideal for outdoor activities such as hiking the scenic trails in the Catskills or enjoying leisurely strolls through the charming streets lined with art galleries and boutique shops. The energy of Woodstock during this season is infectious, fostering a sense of community among visitors and locals alike.

For those considering a more budget-friendly option, November presents an excellent alternative. This month offers a tranquil atmosphere, superb for those who appreciate the beauty of autumn foliage and the serene landscapes that surround the town. While the pace is slower, visitors can still enjoy the breathtaking views and perhaps even find unique local events that showcase Woodstock's artistic spirit.

Ultimately, the best time to visit Woodstock for a vacation rental depends on your preferences—whether you want to soak in the vibrant summer energy or savor the peacefulness of late fall.
How early should I book a Woodstock vacation rental?
Book your Woodstock vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodstock?
In Woodstock, New York, visitors can take part in a rich artistic and cultural scene. The town is famous for its vibrant arts community, with attractions such as the Woodstock Artists Association & Museum located in the heart of the village, showcasing local artists' works. Nearby, the iconic Woodstock Playhouse offers a variety of performances throughout the year, making it a popular spot for theater enthusiasts.

For outdoor lovers, the nearby Catskill Mountains provide numerous hiking trails and breathtaking views, with popular spots like Overlook Mountain and Kaaterskill Falls within a short drive. The charming streets of the village are lined with unique shops, cafes, and restaurants, contributing to the town's bohemian atmosphere.

Additionally, the annual Woodstock Film Festival draws visitors to the area, enhancing its reputation as a cultural hub.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Woodstock vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.