Woodstock holiday lettings

We found 753 holiday rentals — enter your dates for availability

Discover a selection of 74 homes, 13 apartments and other holiday rentals in Woodstock that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Woodstock

Showing deals for:2 Oct - 9 Oct

Image gallery for Large 11 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville

Pool
9.0 out of 10, Wonderful, (22 reviews)
Wonderful
(22 reviews)

Large 11 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville

Tannersville

12% off
Price is £4,341
for 7 nights, 1 home
£620 per night
includes taxes & fees
Large 11 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville

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Why visit Woodstock

  • Stunning Natural Landscapes: Explore the breathtaking views of the Catskill Mountains, perfect for hiking and cycling enthusiasts.
  • Rich Artistic Heritage: Immerse yourself in Woodstock's vibrant arts scene, filled with local galleries and unique shops.
  • Historic Woodstock Festival Legacy: Visit the Woodstock Museum to appreciate the town's iconic musical history and cultural significance.
  • Outdoor Activities: Enjoy horseback riding and discover serene nature reserves and picturesque waterfalls.
  • Family-Friendly Atmosphere: Experience charming local eateries and peaceful parks, ideal for a relaxing getaway with loved ones.

Popular types of accommodation in Woodstock

Welcome to Woodstock, New York, a charming town steeped in artistic heritage and natural beauty. Here, you can explore stunning landscapes, vibrant arts scenes, and local attractions like peaceful parks and historic sites. Enjoy a comfortable stay in popular accommodation options such as houses, cabins, and cottages. With a variety of Woodstock vacation rentals available, you’re sure to find the perfect base for your unforgettable getaway.

  • Houses: The top choice for visitors in Woodstock, offering spacious and comfortable living for families and groups.
  • Cabins: A favourite for those seeking a rustic escape, these charming retreats provide a perfect blend of comfort and nature.
  • Cottages: Ideal for a quaint and cozy experience, cottages are a delightful option for couples and smaller families.
  • Apartments: A practical choice for travellers wanting convenience and a homely feel in the heart of Woodstock.
  • Chalets: Offering a unique stay with a blend of modern amenities and alpine charm, chalets are a lovely alternative.**

Top attractions in and around Woodstock

Woodstock, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Visitors can explore scenic nature reserves, marvel at picturesque waterfalls, and enjoy horseback riding at the local equestrian centre. Additionally, the legacy of the iconic Woodstock Festival can be appreciated at the Woodstock Museum, making it a cultural haven. This delightful town promises memorable experiences amidst its beautiful landscapes.

  • Karma Triyana Dharmachakra Monastery: This serene Buddhist monastery offers a peaceful retreat with stunning architecture and cultural vibes, perfect for meditation and reflection amidst beautiful surroundings.
  • Kaaterskill Falls: Although located a short drive from Woodstock, this breathtaking waterfall is a popular outdoor destination, providing a romantic and adventurous atmosphere for hiking and exploring nature.
  • Thorn Preserve - Catskill Center: Nestled in Woodstock, this secluded reserve is ideal for families seeking relaxation, featuring tranquil trails and lush landscapes to unwind and connect with nature.

Things to do recommended for couples

Seeking a romantic getaway in Woodstock? Explore the charming streets filled with art galleries, indulge in a couple's massage at a local spa, or enjoy a scenic hike in the stunning Catskills. Don't forget to savour a candlelit dinner at one of the quaint bistros.

Things to do recommended for families

Families visiting Woodstock can explore the scenic beauty of the Catskill Mountains, enjoy hiking on family-friendly trails, and visit the Woodstock Farm Animal Sanctuary for an up-close experience with rescued animals. Don’t miss the local art scene and charming shops for a delightful afternoon.

Things to do recommended for groups

Groups visiting Woodstock can enjoy hiking in the beautiful Catskill Mountains, explore the vibrant local arts scene at the Woodstock Artists Association, and partake in live music events at iconic venues, creating memorable experiences in this charming town.

*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 travelling with a group, as a family, bringing along your pets, or seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search to include all of these options, and more, on Vrbo.
  • Traveling to Woodstock with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise 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, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Woodstock

Woodstock, New York, offers a unique blend of natural beauty and artistic charm, making it a delightful destination for travellers. Explore the stunning landscapes of the Catskill Mountains while enjoying outdoor adventures like hiking and cycling. The town's vibrant arts scene is complemented by quaint shops and local eateries, perfect for a relaxing family-friendly atmosphere. Whether you're seeking secluded retreats or cultural experiences, Woodstock promises a memorable getaway infused with creativity and nature.

  • Kingston: Situated approximately 16km from Woodstock, Kingston is a vibrant city steeped in history and natural beauty. Known for its outdoor adventures, it offers an array of activities, particularly for skiing enthusiasts seeking thrilling slopes. Visitors can explore nearby ski resorts and fields, making it a perfect destination for winter sports. Additionally, Kingston boasts stunning landmarks such as the majestic mountains and serene lakes, alongside the historic college university that adds to its cultural charm. A visit to Kingston promises a blend of adventure and scenic exploration.
  • Saugerties: Located around 14km from Woodstock, Saugerties is another delightful city that beckons outdoor lovers and adventure seekers. This charming locale is renowned for its ski experiences, with access to top-notch ski fields and resorts. Beyond skiing, visitors can enjoy the picturesque mountains and lakes that surround the area, making it an ideal spot for both relaxation and recreation. Saugerties also features a local stadium, where various events and activities take place, ensuring there’s always something happening in this vibrant community.
  • Bearsville: Just 3km from Woodstock, Bearsville is a quaint city that offers stunning scenery and outdoor adventures. This close-knit community is perfect for those looking to immerse themselves in nature, with ample opportunities for skiing, hiking, and enjoying the breathtaking landscapes. Bearsville is home to beautiful mountains, tranquil lakes, and captivating waterfalls that make for memorable experiences. Visitors can soak in the area's natural beauty while partaking in various outdoor activities, ensuring a fulfilling getaway in this picturesque setting.

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 reduce your travel expenses for your next adventure? We recommend being open to adjusting your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly create new trips, resume planning from where you last stopped, or easily view and organise your travel arrangements. You’ll discover your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the lush landscape of Woodstock

Enjoy the art galleries and other features of Woodstock. Travellers to this relaxing city praise the hiking, forests and riverfront. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Woodstock

Are you looking for top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Woodstock a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 an outdoor enthusiast or just want to spend some time taking in the scenery, Woodstock is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Opus 40 (4.5 mi / 7.2 km)
  • Esopus Creek (8.7 mi / 14 km)
  • Forsyth Park (8.8 mi / 14.1 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 centre.

Frequently asked questions

What is the best area to stay in Woodstock when booking a holiday rental?
When considering a holiday 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 holiday home in Woodstock?
Prices for holiday 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 holiday 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 holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of holiday 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 holiday 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 holiday home with a pool or hot tub in Woodstock?
In Woodstock, there are many holiday 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. Find your rental in Woodstock with a pool or a hot tub.
Can I find long-stay holiday rentals in Woodstock?
A long-stay holiday 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.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, New York, there are numerous remote work holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday 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 holiday rental?
Book your Woodstock holiday 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 holiday 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 holiday 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 holiday 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 as applicable.

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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