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Woodstock vacation rentals

We found 742 vacation rentals — enter your dates for availability

Discover a selection of 69 homes, 12 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:Feb 20 - Feb 27

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Pool
9.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Woodstock, NY

20% off
Price is CA $361
CA $3,248 total
includes taxes & fees
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

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Find out more about Woodstock

Why visit Woodstock

  • Outdoor Adventures: Woodstock offers a plethora of scenic nature reserves and picturesque waterfalls, perfect for outdoor enthusiasts.
  • Cultural Experiences: Visit the Woodstock Art Gallery and enjoy the renowned Woodstock Film Festival for a taste of local culture.
  • Charming Accommodations: Choose from a variety of cozy cottages and vacation rentals tailored to families and peaceful retreats.
  • Family-Friendly Activities: Enjoy diverse activities suitable for all ages, making it an ideal destination for family vacations.
  • Rich History: Explore the vibrant urban atmosphere and historical sites that add to Woodstock's unique charm.

Popular types of accommodation in Woodstock

Discover the charm of Woodstock with our selection of vacation rentals. Whether you're seeking a private vacation home, a cozy cabin, or a quaint cottage, we have the perfect spot for you. From Airbnb options to home rentals, Woodstock offers diverse accommodations tailored to your needs. Enjoy your getaway with transparency and savings, knowing you’ve found the ideal retreat in this picturesque Canadian destination.

  • Houses: The top choice for visitors to Woodstock, these homes offer a comfortable and spacious setting for families, friends, or couples to enjoy their getaway.
  • Cabins: A close second, cabins provide a rustic escape, perfect for those seeking a nature-filled experience in the beautiful surroundings of Woodstock.
  • Cottages: These quaint options are ideal for a cozy, intimate stay, giving you a charming home base during your vacation.
  • Apartments: A practical choice for solo travellers or couples, apartments offer modern amenities in a compact space.
  • Chalets: These delightful accommodations blend comfort with a touch of alpine charm, making them a unique option for your trip.**

Top attractions in and around Woodstock

Woodstock, New York, is perfect for outdoor enthusiasts and those seeking scenic adventures. Visitors can explore nature reserves, picturesque waterfalls, and historic colleges. Key attractions include the Woodstock Golf Club, the Woodstock Film Festival, and the Woodstock Art Gallery, offering a blend of culture and family experiences. Whether you're looking for a waterfront getaway or local events, Woodstock promises an enriching vacation.

  • Kaaterskill Falls: A stunning two-tiered waterfall, Kaaterskill Falls offers breathtaking views and a chance for adventure. Surrounded by lush forests, it's perfect for hiking and picnicking, making it an ideal romantic getaway.
  • Bard College: This historic institution boasts beautiful architecture and scenic landscapes, providing a rich cultural experience. Visitors can explore its art galleries, gardens, and enjoy various performances that highlight the vibrant campus life.
  • Karma Triyana Dharmachakra Monastery: Nestled in Woodstock, this serene monastery is a hub for Buddhist teachings and meditation. Its peaceful grounds and stunning architecture create a tranquil atmosphere for reflection and spiritual growth.

Things to do recommended for couples

Looking for a romantic getaway in Woodstock? Enjoy the thrill of skiing at Hunter Mountain, unwind at Copperhood Retreat & Spa, or sip fine wines at El Paso Winery. Each spot offers a unique blend of adventure, relaxation, and romance perfect for couples.

Things to do recommended for families

Experience the thrill of ice skating at Kiwanis Ice Arena, unwind at Saugerties Village Beach, or catch a game at Dietz Stadium. Each location, within a short drive from Woodstock, offers family-friendly fun and entertainment for everyone to enjoy.

Things to do recommended for groups

Embark on a hike at Overlook Mountain Trailhead for stunning views or enjoy a round of golf at Woodstock Golf Club. For a family-friendly experience, head to North-South Lake Campground, located 19.3km from Woodstock, perfect for outdoor adventures and bonding.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with friends, family, or even pets, or if you're considering an extended stay, it's important to refine your search based on your specific needs. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young children 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, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many families, a vacation just wouldn’t be the same without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Woodstock

Woodstock, New York, offers a delightful mix of outdoor adventures and serene getaways. With its charming cottage rentals and scenic waterfront settings, it's perfect for families and those seeking a peaceful retreat. Nearby areas exude a friendly atmosphere, rich history, and urban vibrancy. As you explore, you'll discover the best of both relaxation and adventure, making Woodstock an ideal destination for your next vacation.

  • Kingston: Kingston is a vibrant city located 16.1km from Woodstock, offering a captivating blend of outdoor adventure and rich history. Nestled between the Hudson River and the Catskill Mountains, it serves as a gateway to various outdoor activities, including skiing at nearby resorts. Explore the scenic beauty of the region with its lakes and mountainous terrain, or visit historic landmarks such as the local college university. With its charming downtown area filled with shops, restaurants, and cultural sites, Kingston is an ideal spot for both relaxation and adventure seekers.
  • Saugerties: Situated 14.5km from Woodstock, Saugerties is a delightful city that attracts visitors with its stunning natural surroundings and outdoor activities. Known for its adventure opportunities, Saugerties boasts proximity to ski fields and resorts, making it a favourite winter destination. Visitors can also enjoy the picturesque landscape dotted with mountains and lakes, or catch a game at the local stadium. With its quaint shops and eateries, Saugerties offers a charming atmosphere perfect for exploring and unwinding.
  • Bearsville: Just 3.2km from Woodstock, Bearsville is a hidden gem known for its breathtaking scenery and outdoor pursuits. This idyllic city is surrounded by mountains and lakes, providing ample opportunities for hiking, skiing, and enjoying nature. Visitors can explore the nearby national state park, where trails and natural wonders await. Bearsville's close-knit community and artistic vibe create a unique atmosphere, making it an excellent destination for those looking to escape into nature while enjoying local culture.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageSlightly Low
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 HighAverage
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 simple

Are you aiming to save on your upcoming adventure? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, if you consider booking a longer stay, you could enjoy considerable savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is your go-to tool for planning future getaways, managing your travel arrangements, and reviewing your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To start exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Delight in the lush landscape of Woodstock

Enjoy the art galleries and other features of Woodstock. Travelers to this relaxing city praise the hiking, forests and riverfront. Hunter Mountain and Catskill Mountains are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

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 (12.4 mi / 19.9 km)
  • Indian Head Mountain (6.5 mi / 10.5 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (10.8 mi / 17.3 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Mohonk Golf Course (18.1 mi / 29.2 km)
  • Windham Mountain Resort (18.6 mi / 30 km)

Exploring the natural features in Woodstock

Whether you're looking for adventure or just want to appreciate the scenery, Woodstock is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Catskill Mountains (13.7 mi / 22.1 km)
  • Overlook Mountain Trailhead (2.1 mi / 3.4 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (3.5 mi / 5.6 km)
  • Esopus Creek (8.7 mi / 14 km)
  • Saugerties Village Beach (8.8 mi / 14.2 km)
  • Falling Waters Preserve (9 mi / 14.5 km)

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

What is the best area to stay in Woodstock when booking a vacation rental?
When considering a vacation rental in Woodstock, New York, the heart of the town is a popular area to stay. This vibrant neighbourhood is steeped in artistic history and is home to a variety of charming shops, galleries, and eateries that reflect its bohemian spirit. You can explore the iconic Woodstock Artists Association and Museum, which showcases local art and hosts numerous exhibitions throughout the year. Additionally, the picturesque Woodstock Town Park offers beautiful walking trails and a serene setting for picnics, making it a great spot for relaxation.

Another fantastic area to consider is the vicinity of the Bethel Woods Centre for the Arts, located a short drive from the town centre. This venue, famous for its connection to the original Woodstock Festival, hosts a wide array of concerts and cultural events. Staying near this area provides easy access to both the historical significance of the site and the natural beauty of the surrounding landscape, which is great for hiking and exploring.
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 travelling 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.
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 the best ski resort rentals near Woodstock, New York, travellers should consider the nearby Hunter Mountain area, which offers a variety of accommodation options for those looking to hit the slopes. In the towns surrounding Hunter Mountain, such as Tannersville and Haines Falls, visitors can find charming cabins and modern chalets that cater to different group sizes. Many of these properties come equipped with amenities like fully stocked kitchens, spacious living areas with fireplaces, and hot tubs, providing a superb retreat after a day of skiing.

In addition to the skiing, the area offers beautiful mountain views and access to local attractions, including hiking trails and scenic lookouts. Rentals in Tannersville often feature proximity to the slopes, with some properties located within walking distance of ski lifts, making it convenient for guests to enjoy a day on the mountain without the hassle of transportation. The vibrant local scene also means that visitors can take advantage of nearby restaurants and shops, enhancing their overall experience.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular rental option, with around 54 available in the area. These houses provide ample space and comfort, featuring multiple bedrooms, fully equipped kitchens, and often outdoor areas for relaxation, making them ideal for families or larger groups. Additionally, there are about 17 charming cottages that offer a quaint and cosy atmosphere, typically located in scenic spots near the town centre and local hiking trails. For those looking for a more rustic experience, several cabins and chalets can also be found, providing a unique escape into nature.
Are there any family house rentals in Woodstock?
In Woodstock, New York, there is a wide selection of family-friendly vacation rentals, with about 67 properties available. This charming town, known for its artistic community and stunning natural surroundings, offers various accommodations suitable for families. Many homes feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play and families can gather.

Visitors can enjoy amenities such as multiple bedrooms for added privacy, laundry facilities for convenience, and some properties even come with private pools or game rooms to keep everyone entertained.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, New York, there are plenty of vacation homes available for rent that come with pools and hot tubs, with around 25 options to choose from. This picturesque town, known for its artistic community and stunning natural surroundings, offers a variety of properties in charming neighbourhoods such as the historic village centre and the scenic areas near the Catskill Mountains.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, there are numerous pet-friendly house rentals available, with around 41 options to choose from. This charming town is located in the picturesque Catskill Mountains, providing a serene backdrop for a getaway. Many of these vacation rentals come equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces like patios or gardens, ideal for both pets and their owners to enjoy. 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 80 options to choose from. This charming town is known for its artistic vibe and natural beauty, making it an ideal spot for working remotely while enjoying a serene environment. Many properties offer dedicated workspaces, including desks and comfortable chairs, along with essential amenities such as Wi-Fi and computer monitors to facilitate productivity. 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 travellers 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, popular vacation rentals typically include essential amenities that cater to a comfortable stay. Most properties feature fully equipped kitchens with appliances such as microwaves, refrigerators, toasters, and cookware, allowing guests to prepare their own meals. This is particularly appealing for those looking to enjoy the local produce and culinary offerings. Additionally, many rentals come with cosy living areas, which create an inviting space for relaxation after a day of exploring the picturesque surroundings, including the nearby Catskill Mountains and vibrant arts scene in the town.
When is the best time to visit Woodstock for a vacation rental?
July marks the peak season for visiting Woodstock, drawing in vacationmakers eager to experience the vibrant arts scene and picturesque landscapes. During this time, the warm weather creates a friendly space for outdoor activities, from hiking through the scenic Catskills to exploring local art galleries and quaint shops. Expect daytime temperatures to hover around the low to mid-20s Celsius, superb for enjoying the lush greenery and engaging in various outdoor pursuits.

As summer unfolds, particularly in August and September, Woodstock maintains its allure with numerous festivals and events that celebrate music, art, and culture. This bustling period allows visitors to immerse themselves in the local community, soaking up the lively spirit that defines this charming town.

For those seeking a more tranquil experience, consider planning your visit in November. This month offers a serene atmosphere with fewer tourists, allowing for a more intimate exploration of the area's stunning fall foliage, as well as the opportunity to enjoy local cafés and shops without the crowds. The crisp air and beautiful autumn colours create a picturesque backdrop for leisurely strolls and scenic drives.
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 immerse themselves in a rich tapestry of artistic and natural attractions. The town is renowned for its vibrant arts scene, with the Woodstock Artists Association and Museum showcasing local and regional artists. Nearby, the picturesque Overlook Mountain offers hiking trails leading to stunning views and the remnants of an old hotel at the summit, making it a popular spot for outdoor enthusiasts.
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 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 travellers 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 cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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