Photo by Marina Timo

Woodstock holiday lettings

We found 751 holiday rentals — enter your dates for availability

Discover a selection of 70 homes, 14 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:29 May - 5 Jun

Image gallery for Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!

Beautiful fire pit with view of Overlook Mountain
10 out of 10, Exceptional, (205 reviews)
Exceptional
(205 reviews)

Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!

Woodstock

8% off
Price is £2,485
for 7 nights, 1 chalet
£355 per night
includes taxes & fees
Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Woodstock

  • Outdoor Adventures: Experience stunning nature reserves, ideal for hiking and exploration amidst breathtaking landscapes.
  • Historic Vibes: Discover the rich heritage of New Woodstock with its quaint historic sites and picturesque surroundings.
  • Charming Accommodations: Choose from a variety of delightful holiday homes, cosy cottages, and charming cabins for your stay.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment with activities suitable for visitors of all ages.
  • Scenic Waterfalls: Visit captivating waterfalls that enhance the natural beauty of the region.

Popular types of accommodation in Woodstock

If you're pondering on the ideal accommodation for your getaway in Woodstock, look no further! Our platform offers a delightful range of options, including private holiday homes, charming cabins, and cosy cottages. Whether you seek Woodstock holiday rentals, apartment options, or serene cabin retreats, we have something to suit every taste and budget. Explore our selection of Woodstock rentals and enjoy a memorable stay in this picturesque location!

  • Houses: The top choice for accommodation in Woodstock, ideal for families, friends, or couples seeking a home-away-from-home experience.
  • Cabins: A rustic and charming option, these retreats provide a peaceful escape surrounded by nature.
  • Cottages: Quaint and cosy, perfect for those wanting a romantic getaway or a tranquil retreat.
  • Apartments: Convenient and versatile, these rentals offer a comfortable stay with easy access to local amenities.
  • Chalets: A delightful choice, often featuring stunning views and a warm atmosphere for a unique holiday experience.**

Top attractions near Woodstock

Woodstock, New York, is a charming destination perfect for outdoor enthusiasts and adventure seekers. Visitors can explore captivating points of interest, including nature reserves, historic colleges, and picturesque waterfalls. This delightful town offers a blend of cultural experiences and family-friendly activities, ensuring an enjoyable getaway that showcases the stunning scenery and rich heritage of the area.

  • Bethel Woods Museum: Located 1.9km from Woodstock, this museum offers a rich cultural experience, celebrating the legacy of the 1969 Woodstock Festival and the arts, with engaging exhibits and events.
  • Bard College: Situated 6.8km away, this historic campus boasts stunning architecture and a vibrant arts scene, making it a perfect spot for cultural enrichment and leisurely strolls.
  • Kaaterskill Falls: This breathtaking waterfall, also 6.8km from Woodstock, is a must-visit for outdoor enthusiasts, offering scenic hiking trails and a romantic atmosphere amidst nature's beauty.

Things to do recommended for couples

For a romantic getaway in Woodstock, explore the thrilling slopes of Hunter Mountain, indulge in a rejuvenating treatment at Copperhood Retreat & Spa, or take an adventurous ride on the H Ski Lift. Each experience promises to create unforgettable memories together in this charming town.

Things to do recommended for families

Families visiting Woodstock can unwind at Saugerties Village Beach, a lovely recreation park, or enjoy the sporting atmosphere at Dietz Stadium. For some thrilling fun, the Kiwanis Ice Arena offers ice skating adventures, making it a perfect day out for the whole family.

Things to do recommended for groups

Groups visiting Woodstock can hike the Overlook Mountain Trailhead for breathtaking views, explore musical treasures at the Woodstock Music Shop, and enjoy a round of golf at the scenic Woodstock Golf Club, perfect for outdoor enthusiasts and sports lovers alike.

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

Regardless of whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s important to filter based on your specific priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for 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 fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Woodstock

Woodstock, New York, offers a delightful blend of outdoor adventure and serene landscapes, perfect for a relaxing getaway. Explore the charming town with its family-friendly atmosphere and friendly locals. Nearby, discover the historical vibes of New Woodstock and other picturesque regions that promise scenic views and a sense of seclusion. Whether you're seeking a peaceful retreat or an urban escape, Woodstock is an ideal destination for your next holiday adventure.

  • Kingston: Located a mere 6.2km from Woodstock, Kingston is a city steeped in history and natural beauty. Renowned for its outdoor adventures, visitors can engage in skiing at nearby resorts and explore scenic mountain trails. The city's rich heritage is highlighted by landmarks such as historic colleges and picturesque lakes, making it an ideal destination for those seeking both adventure and culture. Kingston’s vibrant arts scene and charming downtown area offer delightful dining options and boutique shopping, ensuring a well-rounded travel experience.
  • Saugerties: Just 5.6km from Woodstock, Saugerties is a charming city that captivates visitors with its picturesque landscapes and outdoor pursuits. Known for its adventure offerings, the area boasts excellent skiing facilities and access to stunning mountains and lakes. Saugerties also features a lively atmosphere with local events and attractions, including a community stadium. With its blend of natural beauty and recreational opportunities, Saugerties is perfect for those looking to immerse themselves in the great outdoors while enjoying a friendly, small-town vibe.
  • Bearsville: A stone's throw from Woodstock, at only 1.2km away, Bearsville is a quaint community celebrated for its scenic beauty and outdoor activities. This picturesque locale is ideal for adventure seekers, with opportunities for skiing and exploration within nearby national and state parks. Visitors can revel in the stunning views of mountains and lakes, making Bearsville a haven for nature lovers. The close proximity to Woodstock allows for easy access to local arts and culture, ensuring a delightful experience for all who visit.

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 a breeze

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can frequently result in significant savings. To discover the ideal Vrbo accommodation that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new trips, pick up from where you last left off, or review and arrange your travel plans. You can now easily access the properties you’ve saved or booked, organised into Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply 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:

  • Hunter Mountain (12.4 mi / 19.9 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (10.8 mi / 17.3 km)
  • Kaaterskill Falls (10.9 mi / 17.5 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:

  • 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)
  • Saugerties Village Beach (8.8 mi / 14.2 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.

More holiday ideas