Woodstock vacation rentals

We found 773 vacation rentals — enter your dates for availability
Discover a selection of 75 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.

Holiday rentals with weekly discounts - Woodstock

Showing deals for:Nov 6 - Nov 13

Image gallery for Cozy Silo with Sunset Mountain Views near Woodstock

The enchanting Willow Silo
9.8 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Cozy Silo with Sunset Mountain Views near Woodstock

Willow

10% off
Price is CA $915
CA $8,359 total
includes taxes & fees
Cozy Silo with Sunset Mountain Views near Woodstock

Find spaces that suit your style

Find out more about Woodstock

Why visit Woodstock

  • Outdoor Adventures: Enjoy hiking trails, nature preserves, and beautiful waterfalls that showcase the stunning scenery of the Catskills.
  • Cultural Heritage: Immerse yourself in the iconic spirit of the Woodstock Festival, which shaped the town's rich artistic history.
  • Charming Village Atmosphere: Stroll through the quaint village filled with friendly locals, unique shops, and local art.
  • Family-Friendly Activities: Engage in a variety of activities suitable for all ages, ensuring fun for the whole family.
  • Cozy Accommodations: Find a range of inviting holiday rentals, from rustic cabins to modern cottages, perfect for a relaxing stay.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? You're in for a treat. Explore a variety of holiday rentals, including private holiday homes, charming cabins, and cozy cottages that cater to your every need. Whether you're looking for a rustic retreat or a modern apartment, Woodstock has the perfect accommodation for your stay. Discover the local charm and enjoy the peace of mind that comes with transparent and reliable holiday rental options in this beautiful Canadian destination.

  • Private Holiday Homes: These spacious residences offer a home-like environment, perfect for families or groups seeking comfort and privacy during their stay in Woodstock.
  • Cabins: Nestled in nature, these charming retreats provide a rustic experience with cozy interiors, ideal for those wanting to unwind in a serene setting.
  • Cottages: Quaint and inviting, cottages are perfect for a romantic getaway or a peaceful retreat, often surrounded by beautiful landscapes.
  • Apartments: These modern accommodations are well-suited for couples or solo travellers looking for convenience and access to local attractions.
  • Chalets: Offering a blend of comfort and style, chalets are often situated in picturesque locations, making them perfect for relaxation after a day of exploring.**

Top attractions in and around Woodstock

Woodstock, New York, is a fantastic destination for outdoor enthusiasts and families alike, offering stunning scenery and adventure activities. Visitors can explore local attractions such as nature preserves, waterfalls, and equestrian centres, all while soaking in the area's rich cultural history. Don't miss the opportunity to delve into the spirit of the iconic Woodstock Festival, which adds a unique touch to your holiday experience in this charming town.

  • Karma Triyana Dharmachakra Monastery: Nestled in Woodstock, this serene monastery offers a unique cultural experience with its beautiful architecture and peaceful surroundings, perfect for meditation and reflection.
  • Kaaterskill Falls: Located 18km away, this stunning waterfall is a must-see for outdoor enthusiasts, providing a romantic and adventurous setting amidst nature's splendor.
  • HITS-on-the-Hudson: Situated 14km from Woodstock, this equestrian centre showcases thrilling horse shows and events, making it a great destination for horse lovers and families alike.

Things to do recommended for couples

Discover the charm of Woodstock, New York, with your partner. Explore scenic hiking trails together, visit local art galleries, or enjoy a cozy dinner at a quaint restaurant. Don't miss the breathtaking views from Overlook Mountain, perfect for a romantic sunset. It's an idyllic getaway for couples.

Things to do recommended for families

Families visiting Woodstock, New York, can explore the beautiful trails of the Catskill Mountains, enjoy art classes at the Woodstock School of Art, and visit the local farmer's market for fresh produce and handmade goods, providing a delightful and engaging family experience.

Things to do recommended for groups

Explore the vibrant art scene by visiting local galleries and studios or take a scenic hike on the Overlook Mountain trail for breathtaking views. Don't miss a visit to the Woodstock Farm Sanctuary to meet rescued animals and learn about animal welfare.

*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 a group, family, or pets, or if you're interested in extended stays, it's important to refine your search based on your specific needs. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with providing 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 trip isn’t truly complete without their furry companions. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Woodstock: If you're searching for vacation rentals that offer discounts for stays of a month or longer, 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 amenities 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 serene escapes, perfect for your holiday getaway. Explore the charming Woodstock village, where friendly locals create a welcoming atmosphere. Venture into the surrounding areas for picturesque scenery and family-friendly activities, making it an ideal destination for relaxation and exploration. With its rich history and vibrant community, Woodstock promises an unforgettable experience for every traveller.

  • Kingston: Located approximately 16km from Woodstock, Kingston is a vibrant city that offers a plethora of outdoor adventures, particularly for skiing enthusiasts. With its stunning mountains and lakes, visitors can experience a variety of winter sports at nearby ski resorts and fields. In addition to its recreational activities, Kingston boasts a rich history, with landmarks like historic colleges and universities that add to its cultural charm. The blend of adventure and history makes Kingston a must-visit for those seeking both excitement and educational experiences.
  • Saugerties: Situated about 14km from Woodstock, Saugerties is another gem for outdoor lovers and adventure seekers. This city offers similar skiing opportunities, with access to ski fields and resorts ideal for winter sports. The local landscape is dotted with mountains and picturesque lakes, making it perfect for both adrenaline-pumping activities and leisurely exploration. Saugerties also features a vibrant community atmosphere, with local events and attractions that showcase the town's unique character and spirit.
  • Shady: Nestled within the Woodstock area, Shady is a charming village that captivates visitors with its stunning scenery and outdoor activities. Known for its hiking trails and proximity to ski fields, Shady is an excellent choice for those looking to immerse themselves in nature. The village's scenic views of mountains and lakes provide a tranquil backdrop for exploration. Additionally, Shady is home to several historic sites, allowing visitors to appreciate the rich history of the region while enjoying its natural beauty.

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 simple

Are you hoping to save on your next adventure? Being open to adjusting your travel dates can really make a difference, as prices can vary quite a bit. Additionally, if you're able to book a longer stay, you often unlock significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down options by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your travels with ease. You can create new trips, manage your ongoing plans, or review and organize your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the 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. 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:

  • Indian Head Mountain (6.5 mi / 10.5 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Hunter Mountain (12.4 mi / 19.9 km)
  • Copperhood Retreat & Spa (13 mi / 20.9 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:

  • Overlook Mountain Trailhead (2.1 mi / 3.4 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (3.5 mi / 5.6 km)
  • Opus 40 (4.5 mi / 7.2 km)
  • Esopus Creek (8.7 mi / 14 km)
  • Saugerties Village Beach (8.8 mi / 14.2 km)
  • Kaaterskill Falls (10.9 mi / 17.5 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 best area to stay is the town centre. This vibrant locale not only offers a charming atmosphere but also provides easy access to a variety of attractions. You can explore the iconic Woodstock Artists Association & Museum, which celebrates the town's rich artistic heritage, or take a leisurely stroll along the picturesque streets dotted with unique shops and local eateries.

Another appealing option is the surrounding areas, such as Bearsville, which is a bit quieter yet still close to the action. This neighbourhood is known for its serene environment and proximity to the scenic Overlook Mountain, where you can enjoy hiking trails and stunning views. The number of properties available in these areas tends to be varied, suiting different tastes and budgets, ensuring that visitors can find the great accommodation to suit their needs.
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 renting accommodations near the ski resorts in Woodstock, New York, visitors should focus on the area surrounding the nearby Hunter Mountain and Windham Mountain resorts, both of which are within a short drive. In Woodstock itself, travellers can find charming cabins and lodges that offer a rustic yet modern vibe, ideal for a cozy retreat after a day on the slopes. Many of these properties come with amenities such as wood-burning stoves, spacious living areas, and fully equipped kitchens, superb for preparing meals and relaxing in comfort.

In the vicinity of Hunter Mountain, there are a variety of rental options, including ski-in/ski-out condos and larger homes suitable for families or groups. These typically feature convenient amenities like ski storage, hot tubs, and outdoor decks with scenic mountain views, enhancing the overall experience. The warm ambience of these accommodations also provides a ideal setting for family gatherings or après-ski relaxation.

Moreover, the surrounding area offers plenty of opportunities for outdoor activities beyond skiing, such as snowshoeing and hiking trails that are accessible in winter. The vibrant arts scene in Woodstock, including galleries and live music venues, adds to the charm of the area, making it an attractive destination for travellers looking to combine outdoor sports with cultural experiences.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular type of vacation rental, with approximately 208 available throughout the area. These homes often come with spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces like gardens or patios, ideal for families and larger groups. Additionally, there are around 68 charming cottages, which provide a more rustic experience and typically include cosy living areas and outdoor seating, great for enjoying the scenic surroundings. For those seeking more compact options, there are about 32 apartments available, often located near local shops and restaurants, offering modern amenities like kitchen facilities and comfortable living spaces. Lastly, a small selection of cabins and chalets can also be found, providing unique stays that embrace the natural beauty of Woodstock and its tranquil atmosphere.
Are there any family house rentals in Woodstock?
In Woodstock, New York, there are some family-friendly vacation rentals available, with around 67 options spread throughout the area. This charming town is known for its artistic vibe and natural beauty, making it an excellent choice for families. Many properties offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely. Visitors can also expect amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.

Families can explore the nearby attractions, including the scenic beauty of the Catskill Mountains and the vibrant local arts scene. The town is also home to various parks and recreational areas, providing ample opportunities for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, there are many vacation homes available for rent that feature pools and hot tubs, with around 26 options to choose from. This picturesque town, located in the scenic Catskill Mountains, offers a variety of charming neighbourhoods where these properties can be found, including the serene areas surrounding the village centre and the more secluded spots along the nearby streams and forests.

Travellers can expect a range of amenities in these rentals, such as private pools and hot tubs, which are superb for relaxation after a day of exploring the beautiful surroundings. Many properties also come equipped with outdoor decks, fully stocked kitchens, and spacious living areas, making them ideal for families or groups looking to unwind in nature.
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, offering a variety of accommodations to suit different preferences. Many of these properties are set against the backdrop of the stunning Catskill Mountains, providing a tranquil retreat for travellers and their furry companions. Expect amenities such as spacious outdoor areas, fully equipped kitchens, and cosy living spaces, which make these rentals superb for families or groups.

The town itself is known for its artistic vibe and natural beauty, with several parks nearby that welcome pets. The picturesque Woodstock Town Park, for instance, features walking trails and open spaces where pets can enjoy the outdoors. Additionally, the nearby Overlook Mountain offers hiking trails that are pet-friendly, allowing for adventurous outings with your four-legged friends. 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 324 options throughout the area. This charming town is known for its artistic vibe and natural beauty, making it an ideal setting for those looking to balance work and leisure. Many of the properties come equipped with essential amenities for remote work, such as complimentary Wi-Fi, dedicated desk spaces, and comfortable desk chairs, allowing for a productive work environment.

Additionally, these rentals often feature inviting living areas, full kitchens, and outdoor spaces where guests can unwind after a day of work. The scenic surroundings offer opportunities for outdoor activities, including hiking in the nearby Catskill Mountains or exploring local art galleries and shops. 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 rental amenities include fully equipped kitchens, allowing travellers to prepare their own meals during their stay. Many properties feature decks or patios, providing outdoor space for relaxation and enjoying the serene surroundings. Fireplaces are also common, adding a cosy touch, especially during the cooler months. Onsite parking is typically available, making it convenient for guests with vehicles. Additionally, many rentals come equipped with coffee and tea makers, ensuring that guests can enjoy their morning brew at their leisure.
When is the best time to visit Woodstock for a vacation rental?
July marks the peak season for visitors to Woodstock, drawing in those eager to soak up the vibrant setting of this artistic haven. With temperatures typically ranging from 15 to 30 degrees Celsius, the summer months from July to September are ideal for outdoor activities, including hiking in the scenic Catskill Mountains and exploring local art galleries. The town buzzes with energy, making it a great time for those who enjoy live music and cultural events.

During July, the streets of Woodstock come alive with festivals and outdoor concerts, providing ample opportunities for entertainment and socialising. You'll find that many vacation rentals are in high demand, so it's wise to book early to secure your preferred accommodation.

For those looking to visit during a quieter time, November offers a more tranquil experience. While the foliage may have faded, this month presents a wonderful opportunity for peaceful walks and enjoying the serene beauty of the Catskills, as well as exploring local shops and cafes without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Woodstock will depend on whether you prefer the lively summer festivities or the calm, reflective charm of late autumn.
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, visitors can take part in a rich artistic and musical history. The town is renowned for its vibrant arts scene, with attractions such as the Woodstock Artists Association & Museum, which showcases local artists and offers rotating exhibitions. The picturesque streets are lined with charming shops, galleries, and cafes, making it a delightful area to explore on foot.

For nature enthusiasts, the nearby Overlook Mountain offers hiking trails that lead to stunning views and the remnants of an old hotel. The scenic Ashokan Reservoir, located just a short drive away, provides opportunities for photography, walking, and cycling along its beautiful paths.

Additionally, the historic Bearsville Theatre is a must-visit for music lovers, often hosting live performances and events that celebrate the town's musical legacy.
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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