Bearsville vacation rentals

We found 385 vacation rentals — enter your dates for availability

Discover a selection of 17 homes and other vacation rentals in Bearsville 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, such as air conditioning and WiFi. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Bearsville

Showing deals for:Oct 31 - Nov 7

Image gallery for Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

Outdoor dining
10 out of 10 rating
Exceptional
(5 reviews)

Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

Saugerties, NY

13% off
Price is $432
$3,021 for 7 nights
All fees included
Woodland Whimsy a private escape w/ hot tub, pool, sunroom on 3 acres

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Find out more about Bearsville

Find out more about Bearsville

Find the perfect vacation rental for your Bearsville getaway

Learn about the unique charm of Bearsville with a stay in a private vacation home. This city has something for everyone. Hunter Mountain and Catskill Mountains are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Bearsville

Are you hoping to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Bearsville has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (11.6 mi / 18.6 km)
  • Indian Head Mountain (7 mi / 11.3 km)
  • Kaaterskill Falls (11.6 mi / 18.6 km)
  • Straus Center - Frost Valley YMCA (17.1 mi / 27.6 km)
  • Windham Mountain Resort (17.9 mi / 28.9 km)
  • Belleayre Mountain Ski Center (18.9 mi / 30.4 km)

Exploring the natural features in Bearsville

Whether you're an active traveler or just want to appreciate the scenery, Bearsville is a great place to get out in nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Catskill Mountains (11.7 mi / 18.8 km)
  • Overlook Mountain Trailhead (2.8 mi / 4.4 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (4.7 mi / 7.6 km)
  • Esopus Creek (10.1 mi / 16.3 km)
  • Saugerties Village Beach (10.8 mi / 17.4 km)
  • Falling Waters Preserve (11.1 mi / 17.9 km)

Transportation options to and around Bearsville

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 28.8 mi (46.3 km) from the city center.

Frequently asked questions

What is the best area to stay in Bearsville when booking a vacation rental?
When considering a vacation rental in Bearsville, New York, a popular area to stay is near the iconic Bearsville Theater. This charming neighborhood offers a unique blend of artistic culture and natural beauty, making it great for those looking to experience the vibrant local scene. The theater itself is a top attraction, hosting a variety of live music events and performances that draw visitors from near and far.

Another appealing area is close to the picturesque Ashokan Reservoir. This location provides stunning views and a peaceful atmosphere, ideal for outdoor enthusiasts and those seeking tranquility. The reservoir is not only a great spot for hiking and biking but also offers opportunities for fishing and birdwatching, making it a favorite among nature lovers.

In terms of vacation rental options, the Bearsville area typically boasts a diverse selection of properties, ranging from cozy cabins to stylish cottages, allowing visitors to choose accommodations that best fit their preferences.
How much does it cost to rent a vacation home in Bearsville?
Prices for vacation rentals in Bearsville 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 Bearsville 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 Bearsville vacation house rentals?
You can find great discounts on house rentals in Bearsville 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 Bearsville ski resort rentals?
For ski resort rentals near Bearsville, New York, visitors should focus on the nearby town of Woodstock, which is just a short drive away from the slopes. This area offers a variety of charming accommodations, including cozy cabins and rustic lodges, many of which boast amenities such as wood-burning fireplaces, hot tubs, and expansive decks for enjoying the stunning mountain views.

Travelers can also find larger rental homes suitable for groups or families, often featuring fully equipped kitchens, spacious living areas, and sometimes game rooms for entertainment after a day on the slopes. The surrounding Catskill Mountains provide ample opportunities for outdoor activities beyond skiing, including hiking and snowshoeing in the winter months.

Additionally, the vibrant arts scene and local shops in Woodstock enhance the experience, allowing guests to explore galleries, cafes, and live music venues when they're not hitting the slopes.
What is the most popular type of vacation rental accomodation in Bearsville?
In Bearsville, vacation houses are the most popular type of rental, with about 14 available in the area. These properties typically offer ample space, including multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxing and enjoying the natural surroundings. Additionally, several cottages, cabins, and chalets can be found, each providing a cozy, rustic atmosphere ideal for a retreat. Many of these rentals are located in serene settings, allowing travelers to unwind and immerse themselves in the beauty of the Catskills.
Are there any family house rentals in Bearsville?
In Bearsville, New York, there are numerous family-friendly house rentals available, with around 17 options to choose from. This charming area is known for its natural beauty and proximity to attractions like the iconic Woodstock and the scenic Ashokan Reservoir. Many of these homes provide ample space for families, featuring amenities such as fully equipped kitchens, cozy living rooms, and outdoor decks or patios great for gatherings and relaxation.

Visitors can also find properties with additional features like game rooms or large backyards, ensuring that there's plenty to keep both kids and adults entertained. With local attractions, including hiking trails and artisanal shops, Bearsville offers a delightful mix of leisure and adventure, making it an excellent choice for family getaways.
Can I rent a vacation home with a pool or hot tub in Bearsville?
In Bearsville, New York, travelers can find several vacation homes available for rent that feature pools and hot tubs. This charming area, located near the Catskill Mountains, offers a serene escape with plenty of natural beauty. Many of these rentals come equipped with private pools and hot tubs, providing great spots for relaxation after a day of outdoor activities. Amenities often include spacious living areas, fully equipped kitchens, and outdoor spaces ideal for gatherings.
Can I find long-stay vacation rentals in Bearsville?
A long-stay vacation rental in Bearsville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Bearsville?
In Bearsville, travelers can find a selection of pet-friendly house rentals that cater to various needs. With around eleven options available, visitors have the flexibility to choose accommodations that suit their group size and preferences. Many of these rentals come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, making them ideal for both relaxation and entertaining.

The area itself is known for its picturesque landscapes and proximity to nature, which is great for pet owners looking to enjoy the outdoors with their furry companions. Nearby, the scenic Ashokan Reservoir offers trails and beautiful views, while the surrounding Catskill Mountains provide ample opportunities for hiking and exploring.
Are there any remote work vacation rentals in Bearsville?
In Bearsville, New York, travelers seeking remote work vacation rentals will find around 20 options available. This picturesque area provides a serene environment conducive to productivity, with many properties featuring dedicated workspaces equipped with essential amenities like high-speed Wi-Fi, desks, and ergonomic chairs. Some rentals may also include additional features like computer monitors and safes for added convenience and security.

Nestled in the scenic Catskills region, Bearsville offers a blend of natural beauty and artistic charm. Nearby attractions include the vibrant town of Woodstock, known for its rich history in music and art, where guests can explore local galleries and shops. The surroundings also boast numerous outdoor activities, such as hiking trails and tranquil lakes, superb for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bearsville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bearsville with parking available—perfect for families or travelers 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 Bearsville?
In Bearsville, popular vacation rental amenities include WiFi, kitchens with modern appliances, and outdoor patios for enjoying the serene surroundings. Many rentals feature kitchen islands, making meal preparation social and enjoyable, along with blenders for crafting smoothies or cocktails.
When is the best time to visit Bearsville for a vacation rental?
The most popular time to visit Bearsville is September, when the area comes alive with vibrant autumn colors and a refreshing atmosphere. This month marks the tail end of the peak season, which spans from July to September, drawing in visitors eager to enjoy outdoor activities such as hiking, exploring local art galleries, and attending live music events.

During this period, visitors can experience comfortable temperatures averaging in the low 50s to mid-70s Fahrenheit. The mild climate makes it ideal for leisurely strolls along the scenic trails, where the stunning fall foliage creates a picturesque backdrop for sightseeing.

For those looking for a more budget-friendly option, November offers a quieter experience without compromising on charm. This month presents an excellent opportunity to enjoy the tranquility of Bearsville while taking in the late autumn scenery. It's a great time for cozy indoor activities like visiting local cafes or browsing unique shops.

Ultimately, the best time to visit Bearsville for a vacation rental depends on your preferences—whether you desire the lively summer atmosphere or the peaceful beauty of fall.
How early should I book a Bearsville vacation rental?
Book your Bearsville 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 Bearsville?
In Bearsville, New York, visitors can enjoy a serene atmosphere with a range of attractions. The area is known for its proximity to the iconic Woodstock, where travelers can explore the Woodstock Music Shop and various art galleries that celebrate the town's rich cultural history. Nearby, the beautiful Ashokan Reservoir offers opportunities for hiking, birdwatching, and enjoying scenic vistas.

For those interested in live music, the Bearsville Theater is a top venue, hosting performances by local and touring artists. Outdoor enthusiasts can also take advantage of the nearby Catskill Mountains, which provide ample opportunities for hiking, skiing in the winter, and exploring nature.
Can I change or cancel my Bearsville home rental booking on Vrbo?
To find Bearsville 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 Bearsville 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.

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