Bearsville vacation rentals

We found 405 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:Jul 17 - Jul 24

Image gallery for Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Rear Deck, Hot Tub and Screened Porch
9.8 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

9% off
Price is $391
$2,739 for 7 nights
All fees included
Secluded Cabin with Hot Tub - 5 Miles to Woodstock

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Find out more about Bearsville

Why visit Bearsville

  • Outdoor adventures: Bearsville is a haven for nature lovers, featuring stunning mountains, nature preserves, and picturesque waterfalls.
  • Cultural experiences: Discover local attractions like the Bearsville Theater and immerse yourself in the region's rich history.
  • Charming accommodations: Choose from cozy cabins, delightful cottages, and private vacation homes for a comfortable stay.
  • Proximity to Woodstock: Bearsville's location near Woodstock offers easy access to vibrant arts and music scenes.
  • Family-friendly atmosphere: The area caters to families, ensuring enjoyable activities for all ages amidst beautiful surroundings.

Popular types of accommodation in Bearsville

If you're wondering about the best accommodations in Bearsville, you're in the right place. Our top choices for vacation rentals include charming houses, cozy cabins, and delightful cottages. Whether you're looking for a peaceful Bearsville retreat, a friendly cabin, or a holiday home, we have a variety of options to ensure your stay is comfortable and memorable. Explore your perfect getaway in Bearsville today.

  • Houses: The top choice for travelers in Bearsville, these homes offer spacious and comfortable lodging for families, friends, or couples seeking a home-away-from-home experience.
  • Cabins: A favorite among nature enthusiasts, cabins provide a rustic escape surrounded by scenic beauty and tranquility.
  • Cottages: These charming accommodations offer a quaint and cozy atmosphere, perfect for a romantic getaway or small family vacation.
  • Apartments: Ideal for those seeking convenience, apartments offer modern amenities and easy access to local attractions.
  • Chalets: A unique option, chalets combine comfort and style, often featuring stunning views and a cozy ambiance.**

Top attractions near Bearsville

Bearsville, New York, offers a perfect getaway for outdoor enthusiasts and adventure seekers, featuring stunning mountains, nature preserves, and picturesque waterfalls. Visitors can explore local attractions like the Bearsville Theater and discover cozy cabins near Woodstock. This charming area caters to families and those interested in cultural experiences, ensuring a memorable vacation filled with natural beauty and enriching activities.

  • Catskill Mountains: A stunning range of peaks located 12 miles from Bearsville, the Catskill Mountains offer thrilling outdoor adventures like hiking, rock climbing, and breathtaking scenery. Explore lush forests and enjoy panoramic views that make for unforgettable experiences.
  • Bethel Woods Museum: Situated 5 miles from Bearsville, this cultural gem celebrates the legacy of the 1969 Woodstock Festival. The museum features exhibits on music and art, providing insight into the transformative era of peace and music.
  • Kaaterskill Falls: Just 12 miles away, this picturesque waterfall cascades dramatically, creating a romantic outdoor setting perfect for hiking and photography. Experience the beauty of nature as you explore its scenic trails.

Things to do recommended for couples

For a romantic getaway in Bearsville, explore the thrilling slopes of Hunter Mountain, indulge in relaxation at Copperhood Retreat & Spa, or embark on an adventurous ride at the F Ski Lift. Each experience promises to create unforgettable memories together, just 11 miles away.

Things to do recommended for families

Families can unwind at the Saugerties Village Beach, just 11 miles from Bearsville, or enjoy the excitement of sports at Dietz Stadium, 10 miles away. For a fun adventure, visit the Kiwanis Ice Arena, also 11 miles from Bearsville, perfect for ice skating and family entertainment.

Things to do recommended for groups

Experience the great outdoors at Overlook Mountain Trailhead, located 3 miles away, perfect for hiking enthusiasts. Explore the unique offerings at Woodstock Music Shop, just 2 miles from Bearsville. For a sporty outing, enjoy a day at the Woodstock Golf Club, also 3 miles away.

*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 Bearsville

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Bearsville with a group: Think about how many bedrooms you require, as well as any features like a complete kitchen or outdoor area for gatherings. Thankfully, Vrbo allows you to filter for these options and much more.
  • Traveling to Bearsville with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with providing suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Bearsville: For many families, a vacation wouldn't feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bearsville: If you’re in search of vacation rentals with special rates for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Bearsville

Bearsville, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Nestled near the iconic Woodstock, this area offers a serene getaway with stunning scenery and a friendly atmosphere. Explore the lush landscapes, enjoy relaxing vacation homes, and immerse yourself in the rich history of the region. With its inviting neighborhoods and beautiful surroundings, Bearsville is an ideal spot for a memorable escape in the heart of New York.

  • Woodstock: Located a mere 2 miles from Bearsville, Woodstock is renowned for its vibrant arts scene and stunning natural beauty. This charming town offers a plethora of outdoor activities, making it a perfect destination for adventure seekers. From skiing in the winter to hiking and exploring scenic trails in the warmer months, Woodstock is a haven for nature lovers. Don’t miss the local landmarks such as the picturesque mountain ranges and serene lakes where you can enjoy sunbathing or swimming at nearby beaches.
  • Kingston: Just 11 miles away from Bearsville, Kingston is rich in history and outdoor adventures. As a former capital of New York, it boasts historic architecture alongside modern attractions. Travelers flock to Kingston for skiing and winter sports, with several ski fields and resorts in proximity. Additionally, the local landscape features majestic mountains and beautiful lakes, providing ample opportunities for hiking, fishing, and enjoying the great outdoors. Don’t forget to explore the historic college campuses that add to the city's cultural depth.
  • Saugerties: Also located 11 miles from Bearsville, Saugerties offers a perfect blend of adventure and scenic beauty. Known for its ski resorts and outdoor activities, visitors can enjoy skiing in the winter months and an array of summer adventures including hiking and water sports on nearby lakes. Saugerties is home to stunning natural landmarks like mountains and a local stadium that hosts various events throughout the year, ensuring that there's always something exciting to experience.

Best time to go to Bearsville

If you're planning a trip to Bearsville, 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 February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly SunnyAverageSlightly High
February26.6°F (-3.0°C)Light RainMostly CloudySlightly LowSlightly 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
November39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage
December30.7°F (-0.7°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your next adventures, pick up right where you left off, or manage your existing travel arrangements. You can easily access the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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. 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:

  • Copperhood Retreat & Spa (11 mi / 17.8 km)
  • Hunter Mountain (11.6 mi / 18.6 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)
  • Windham Country Club (18.5 mi / 29.8 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:

  • Overlook Mountain Trailhead (2.8 mi / 4.4 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (4.7 mi / 7.6 km)
  • Opus 40 (6.5 mi / 10.5 km)
  • Forsyth Park (10 mi / 16.1 km)
  • Esopus Creek (10.1 mi / 16.3 km)
  • Saugerties Village Beach (10.8 mi / 17.4 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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Bearsville, New York, the best area to stay is the charming neighborhood surrounding the historic Bearsville Theater. This area not only provides a unique cultural vibe but also places you close to an array of artistic events and performances, making it a fantastic choice for music lovers.

In addition to the theater, the local landscape is beautifully complemented by the stunning scenery of the Catskill Mountains, offering plenty of outdoor activities such as hiking and exploring the natural beauty that the region is known for.

While Bearsville is a small community, it boasts a cozy selection of vacation properties, allowing for a more intimate and personal experience during your stay. This area is superb for those looking to immerse themselves in a peaceful retreat while still enjoying access to nearby attractions and the vibrant setting of Woodstock, which is just a short drive away.
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 those looking for ski resort rentals near Bearsville, the nearby Hunter Mountain area is a prime destination. Just a short drive away, Hunter Mountain offers a variety of vacation rentals that cater to winter sports enthusiasts. In the village of Hunter, visitors can find cozy cabins and spacious chalets, many featuring amenities such as fireplaces, hot tubs, and ski storage to make the après-ski experience enjoyable.

Additionally, properties in the Tannersville area provide easy access to both the slopes and charming local shops and restaurants. Many of these rentals come equipped with fully stocked kitchens and comfortable living areas, superb for relaxing after a day on the mountain. Some accommodations even offer breathtaking views of the Catskill Mountains, ideal for those who appreciate scenic landscapes.

For those interested in exploring more than just skiing, the surrounding area boasts beautiful hiking trails and opportunities for snowshoeing. Rentals in the region also often provide access to outdoor decks or patios, allowing guests to enjoy the crisp mountain air and stunning vistas.
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 13 available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, there are several cabins, cottages, and chalets scattered around, each providing a cozy, rustic atmosphere, often featuring outdoor spaces for enjoying the natural surroundings.
Are there any family house rentals in Bearsville?
In Bearsville, New York, families will find a variety of suitable vacation rentals—about 17 options available throughout the area. This charming locale is located in the scenic Hudson Valley, providing a peaceful retreat for groups. Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where kids can enjoy fresh air and play. Visitors can also expect amenities such as Wi-Fi and air conditioning to enhance their comfort during their stay.

Families will appreciate the close proximity to attractions like the Woodstock town center, known for its vibrant arts scene, shops, and restaurants. The nearby Catskill Mountains offer ample opportunities for hiking, biking, and exploring nature, making Bearsville a wonderful destination for both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Bearsville?
In Bearsville, there are several vacation homes available for rent that feature pools and hot tubs, providing great options for travelers looking to relax in style. This charming area, located in the scenic Catskills, offers a tranquil escape with easy access to outdoor activities such as hiking and exploring the beautiful surrounding landscapes.

Many of the vacation rentals in Bearsville come equipped with desirable amenities, including private pools, inviting hot tubs, spacious outdoor decks, and fully equipped kitchens, making them superb for family gatherings or group retreats. Additionally, you may find properties with features like fire pits and game rooms, enhancing the overall experience for guests.
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 will find a variety of pet-friendly house rentals, with around 12 options available to choose from. Many of these vacation homes come equipped with modern amenities such as full kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. The area is known for its charming, natural surroundings, making it an appealing destination for those looking to escape into the beauty of the Catskills.

Nearby, there are several parks and hiking trails that are pet-friendly, allowing guests to explore the stunning landscapes and enjoy outdoor activities with their furry companions. The proximity to the scenic Ashokan Reservoir adds to the allure, providing opportunities for leisurely walks and picnics.
Are there any remote work vacation rentals in Bearsville?
In Bearsville, New York, there are several remote work vacation rentals available, with around 22 options to choose from. These rentals are well-suited for those looking to balance work and leisure in a serene environment. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas that make it easy to focus while enjoying the tranquil surroundings.

Located near the scenic beauty of the Catskill Mountains, these rentals offer a peaceful retreat, great for unwinding after a productive day. Furthermore, Bearsville is close to various local attractions, including art galleries and music venues, which can provide a refreshing break from 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 rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals, and cozy fireplaces that create a warm atmosphere during cooler months. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the natural surroundings. Additionally, travelers can expect amenities such as coffee and tea makers, superb for those who enjoy a morning brew while taking in the serene views.
When is the best time to visit Bearsville for a vacation rental?
September is the most popular time to visit Bearsville, making it an ideal choice for travelers looking to experience the charm of this quaint New York town. This month falls within the peak season, which spans from July to September, and offers a delightful blend of warm weather and vibrant autumn colors. Visitors can take part in the local culture, enjoy outdoor activities, and explore the picturesque surroundings.

During September, temperatures typically range from the mid-50s to low 70s Fahrenheit, providing a comfortable climate for hiking, sightseeing, and taking in the stunning views of the Catskill Mountains. This is an excellent time to stroll through local farmers' markets or attend community events, as the atmosphere is lively yet relaxed.

For those seeking a more budget-friendly option, November presents a quieter time to visit Bearsville. This month allows travelers to enjoy the peacefulness of the area while still experiencing its natural beauty. The crisp autumn air is superb for leisurely walks and enjoying the serene landscapes without the crowds.

Ultimately, the best time to book a vacation rental in Bearsville depends on your preferences for either vibrant summer activities or a tranquil fall escape.
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, New York, United States of America?
In Bearsville, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and artistic culture. The nearby Woodstock area is famous for its vibrant arts scene, with numerous galleries and music venues, including the iconic Woodstock Playhouse, which hosts live performances and events throughout the year.

For nature enthusiasts, the stunning scenery of the Catskill Mountains offers opportunities for hiking, with trails leading to scenic vistas and waterfalls. The Ashokan Reservoir is also a popular spot for outdoor activities, including fishing and birdwatching, and features a beautiful walking and biking path that runs along its perimeter.

Bearsville's close proximity to the charming town of Woodstock means visitors can easily explore its boutique shops, cafes, and historic sites, including the Woodstock Museum. The area's rich history in music and arts continues to attract visitors looking to experience its cultural heritage.
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 cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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