Photo by Marina Timo

Woodstock holiday lettings

We found 749 holiday rentals — enter your dates for availability

Discover a selection of 68 homes, 11 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:16 Jan - 23 Jan

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

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

16% off
Price is £1,790
for 7 nights, 1 cottage
£256 per night
includes taxes & fees
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

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. Hunter Mountain and Catskill Mountains are just a couple of the must-see attractions in the area. 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)
  • Indian Head Mountain (6.5 mi / 10.5 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)
  • Woodstock Golf Club (0.5 mi / 0.8 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)
  • 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, a popular area to stay is the vicinity of the Village Centre. This charming neighbourhood boasts a vibrant atmosphere, with an array of delightful shops, art galleries, and a variety of restaurants that cater to diverse tastes. Staying here places you within walking distance of the iconic Woodstock Playhouse, known for its live performances and rich artistic history, as well as the picturesque Woodstock Farmers Market, where you can explore local produce and artisanal goods.

Another excellent option is the area around the Ashokan Reservoir. This serene locale offers breathtaking views and opportunities for outdoor activities such as hiking and birdwatching. The reservoir itself is a popular spot for scenic walks and photography, making it a tranquil retreat after a day of exploring. While this area may have fewer properties compared to the Village Centre, the rentals available often provide a more secluded and nature-oriented experience.
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 those seeking ski resort rentals in Woodstock, New York, the nearby Catskill Mountains offer excellent options. The region is home to several ski areas, with Hunter Mountain and Belleayre Mountain being the most accessible for skiers and snowboarders. In Woodstock itself, travellers can find a variety of charming cabins and lodges that provide a rustic atmosphere while being just a short drive from the slopes.

Many properties in Woodstock feature amenities such as wood-burning fireplaces, spacious living areas, and outdoor decks, great for enjoying the serene winter landscape. Some rentals may also include hot tubs and access to hiking trails, allowing guests to unwind after a day of skiing or snowboarding. The area is known for its artistic vibe, so visitors can also expect unique, creatively decorated spaces that reflect the local culture.
What is the most popular type of holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of rental, with around 54 available in the area. These homes are often located in picturesque settings, providing a great retreat for visitors looking to enjoy the natural beauty of the Catskills. Most holiday houses come with multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or patios for relaxation.
Are there any family house rentals in Woodstock?
In Woodstock, New York, there are numerous family-friendly holiday rentals available, with around 67 options to choose from. This charming town, known for its artistic vibe and stunning natural scenery, offers a variety of accommodations suitable for families. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Visitors can find homes with amenities such as comfortable bedrooms, modern bathrooms, and sometimes even game rooms or private gardens, great for relaxation after a day of adventures. The locale is close to attractions like the Woodstock Playhouse and the beautiful hiking trails of the Catskill Mountains, making it an ideal base for both outdoor activities and cultural experiences.
Can I rent a holiday home with a pool or hot tub in Woodstock?
In Woodstock, New York, there are several holiday homes available for rent that feature pools or hot tubs, with around 25 options to choose from. This picturesque town is renowned for its artistic heritage and natural beauty, making it a popular destination for travellers seeking relaxation and recreation. Many of the rentals in the area come with amenities such as private swimming pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, great for enjoying time with family and friends. 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, providing travellers with a variety of options for their stay. Many of these rentals come equipped with modern amenities such as fully stocked kitchens, comfortable living spaces, and outdoor areas where pets can play. The charm of the area is enhanced by the beautiful surroundings, including the picturesque Catskill Mountains, making it a great destination for those wishing to explore nature with their furry companions.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, New York, there are numerous remote work-friendly holiday rentals available—around 80 to choose from. This picturesque town, known for its vibrant arts scene and stunning natural landscapes, offers a variety of accommodations equipped to meet the needs of remote workers. Many properties come with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and office chairs, and safe storage options. Some rentals even feature computer monitors for added convenience. 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 holiday 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 holiday rental?
July is the most popular time to visit Woodstock, as the summer months from July to September draw in a vibrant crowd of travellers seeking a mix of outdoor adventures and cultural experiences. This peak season is ideal for those who enjoy hiking the scenic trails of the Catskill Mountains, exploring local art galleries, or attending one of the many summer festivals that celebrate the town's rich artistic heritage.

During July, visitors can expect warm temperatures averaging around the mid-20s Celsius, making it a superb time for outdoor activities such as kayaking on the nearby Ashokan Reservoir or strolling through the charming streets lined with shops and cafés. The lively atmosphere during this month creates a sense of community, with events often taking place that showcase local musicians and artisans.

If you're looking for a more budget-friendly option, consider planning your trip in November. This month offers a serene and picturesque setting as the fall foliage wanes, providing a quieter experience and the opportunity to enjoy the peaceful natural beauty of the area without the crowds. It's a lovely time for reflective walks or cozy afternoons in local cafés, where you can warm up with a hot drink.
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 engage in a rich artistic and musical heritage. The town's vibrant arts scene is highlighted by the Woodstock Artists Association & Museum, which showcases local artists and hosts various exhibitions throughout the year. Many holiday rentals in the area reflect the artistic spirit, featuring unique decor and proximity to local galleries.

The iconic Woodstock Music Festival site is a significant draw, with its historical significance and scenic views. Nearby, the charming Village Green offers a lovely space for leisurely strolls and community events. For nature enthusiasts, the surrounding Catskill Mountains provide ample opportunities for hiking and outdoor activities, with trails leading to stunning vistas and waterfalls.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Woodstock 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.

More holiday ideas