Best Vacation Homes in Bearsville
Apartment
10.0(244 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
£229/Night
7 Nights - £1,602
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1044.1 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Parking
£134/Night
7 Nights - £936
House
9.8(112 Reviews)
1 Bedroom
1 Bath
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£146/Night
7 Nights - £1,026
Cottage
10.0(178 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£326/Night
7 Nights - £2,282
Bed & Breakfast
9.8(27 Reviews)
4 Bedrooms
6 Baths
12 Guests
500.52 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
£221/Night
7 Nights - £1,549
Cabin
10.0(134 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
£268/Night
7 Nights - £1,875
Cabin
10.0(129 Reviews)
1 Bedroom
1 Bath
3 Guests
1200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£252/Night
7 Nights - £1,767
Cottage
10.0(124 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£272/Night
7 Nights - £1,901
Bearsville Luxury Rentals
House
10.0(40 Reviews)
5 Bedrooms
5 Baths
10 Guests
5600 ft²
Private Pool- Hot Tub
Spa- Fireplace/Heating
£1,891/Night
7 Nights - £13,234
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
£970/Night
7 Nights - £6,790
House
10.0(106 Reviews)
3 Bedrooms
3 Baths
8 Guests
2650 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£895/Night
7 Nights - £6,263
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
£878/Night
7 Nights - £6,144
House
9.8(9 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
£869/Night
7 Nights - £6,081
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
6 Guests
3100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£809/Night
7 Nights - £5,666
House
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
£759/Night
7 Nights - £5,314
House
10.0(117 Reviews)
5 Bedrooms
4 Baths
10 Guests
4655 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£746/Night
7 Nights - £5,219
Bearsville Pet Friendly Vacation Rentals
House
10.0(90 Reviews)
2 Bedrooms
2 Baths
6 Guests
1600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£260/Night
7 Nights - £1,821
House
9.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
1140.97 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Parking
£472/Night
7 Nights - £3,303
Ski Chalet
10.0(69 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£168/Night
7 Nights - £1,174
House
8.8(6 Reviews)
2 Bedrooms
1 Bath
3 Guests
731.95 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£205/Night
7 Nights - £1,436
House
10.0(67 Reviews)
2 Bedrooms
1 Bath
5 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£239/Night
7 Nights - £1,671
House
10.0(44 Reviews)
2 Bedrooms
1 Bath
4 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£270/Night
7 Nights - £1,888
House
10.0(27 Reviews)
2 Bedrooms
2 Baths
5 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
£273/Night
7 Nights - £1,913
Cottage
10.0(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
£263/Night
7 Nights - £1,842
Bearsville Large Vacation Homes
House
10.0(130 Reviews)
6 Bedrooms
3 Baths
14 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£683/Night
7 Nights - £4,782
Bed & Breakfast
8.5(63 Reviews)
5 Bedrooms
1 Bath
10 Guests
1235.7 ft²
Skiing- View
- Parking
- Air Conditioner
£148/Night
7 Nights - £1,035
House
10.0(96 Reviews)
4 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£425/Night
7 Nights - £2,978
House
10.0(87 Reviews)
5 Bedrooms
2 Baths
13 Guests
3000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£259/Night
7 Nights - £1,816
Cabin
10.0(73 Reviews)
4 Bedrooms
3 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£549/Night
7 Nights - £3,845
House
10.0(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£609/Night
7 Nights - £4,263
Cabin
9.8(117 Reviews)
4 Bedrooms
2 Baths
12 Guests
1700 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£293/Night
7 Nights - £2,051
House
9.8(52 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£341/Night
7 Nights - £2,389
Why Choose Rent By Owner for your Bearsville Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Bearsville Vacation Rentals
Where are the best neighborhoods to stay in Bearsville?
Discover the charming neighborhoods of Bearsville, New York, where cozy and inviting vacation rentals provide an ideal base for exploring this picturesque area. Whether you prefer staying close to tranquil natural settings or within a vibrant community, Bearsville offers a variety of options that cater to different tastes and preferences. By choosing accommodation in this welcoming region, you'll enjoy easy access to local attractions and scenic landscapes, making your visit both comfortable and memorable. Experience the comfort and convenience of reliable lodging in Bearsville, designed to enhance your overall travel experience in this beautiful part of New York State.
Shady
In this peaceful neighborhood, you can enjoy a quiet retreat surrounded by natural beauty, perfect for relaxing getaways. It offers convenient access to the scenic charm and local attractions that make spending time here memorable.
View 168+ Rentals in ShadyBest Times to Visit Bearsville
When should you plan your Vacation Rentals stay?
Knowing the best time to visit can enhance your stay here, allowing you to enjoy the region's natural beauty and local ambiance at its most vibrant and peaceful moments.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy pleasant weather perfect for exploring the scenic beauty of this destination. The area attracts visitors seeking outdoor activities and vibrant local events, making it an ideal time to book your vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
As the foliage transforms, this destination becomes a stunning backdrop for seasonal festivals and outdoor adventures. The cooler temperatures and colorful scenery draw travelers looking for a memorable autumn experience when reserving vacation rentals.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In the colder months, fewer visitors mean more tranquil surroundings. This season offers a cozy escape with opportunities to enjoy peaceful moments in your rental while experiencing a serene winter landscape here.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
As nature awakens, the region sees fewer tourists, providing a quieter setting for your stay. Spring's mild weather is perfect for those seeking a relaxed atmosphere and blossoming scenery when booking vacation rentals.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Bearsville
How to Book Your Bearsville Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Bearsville
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Access to a private outdoor patio or deck for enjoying the fresh air and scenic views
- Outdoor seating areas perfect for relaxing or communal gatherings amidst nature
- A barbecue grill for preparing meals outdoors during your stay in this picturesque region
- Ample space for outdoor activities such as hiking, biking, or picnicking in the surrounding area
- A fire pit for cozy evenings and roasting marshmallows under the stars
- Beautiful landscaped gardens or natural surroundings enhancing the outdoor experience
- Parking facilities with easy access to outdoor amenities, ensuring convenience during your visit
Top Attractions Around Bearsville
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities and cultural experiences that showcase the natural beauty and vibrant community of Bearsville, New York.
Family Activities
- Woodstock Playhouse: Enjoy a family-friendly theater experience at this historic venue, offering performances and events suitable for all ages in the heart of the area.
- Overlook Mountain Trail: Embark on an accessible hike that offers scenic views of the region while providing a fun outdoor adventure for families exploring here.
- Bearsville Music Festival Grounds: Attend seasonal festivals and live music events set in the picturesque surroundings, perfect for creating lasting memories with loved ones.
- Bicentennial Park: Relax and play at this local park featuring open fields, playgrounds, and picnic areas, ideal for family outings within this destination's scenic setting.
Adult Activities
- Hiking and Nature Walks: Explore the scenic trails around this destination to enjoy breathtaking views and immerse yourself in the region's natural beauty.
- Visit Local Art Galleries: Discover the area's vibrant art scene by browsing galleries showcasing contemporary and traditional works from local artists.
- Gourmet Dining Experiences: Savor farm-to-table cuisine at renowned restaurants that highlight the region's fresh, seasonal ingredients.
- Music and Live Entertainment: Experience the area's lively music venues offering performances across genres, perfect for relaxing evenings after your day adventures.
Bearsville Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature Trails: Take advantage of the scenic outdoor opportunities around here by discovering nearby nature trails, which offer a perfect way to experience the region’s natural beauty firsthand.
- Visit Authentic Local Spots: Immerse yourself in the area's culture by visiting well-loved local eateries and shops that showcase the unique charm of this destination.
- Plan Ahead for Seasonal Events: Check the calendar for seasonal festivals or events happening in the region to enrich your stay with memorable local experiences.
- Choose a Well-Located Vacation Rental: Select a vacation rental that offers easy access to key attractions and outdoor spots to maximize your time exploring this beautiful area.
Transportation Options
- Bearsville Taxi Services: Convenient for quick trips around the area, offering reliable transportation directly to and from local attractions and your vacation rental.
- Regional Bus Lines: Connecting you to nearby towns and cities with scheduled services, making it easy to explore beyond here without a car.
- Rental Car Agencies: Available locally for flexible exploration of the region at your own pace, ideal for visiting the scenic spots surrounding this destination.
- Shared Shuttle Services: Cost-effective options that provide direct transfers between key points in the region, perfect for hassle-free travel during your stay.
Local Customs Options
- Folk Music Tradition: Embrace the area's vibrant folk music scene, which is a cherished part of the local culture and often showcased during community events.
- Artisan Craftsmanship: Discover local artisans whose handcrafted goods reflect the region's creative spirit and dedication to quality craftsmanship.
- Farmers’ Market Etiquette: When visiting markets here, it’s customary to support local farmers by engaging directly with vendors and appreciating fresh, regional produce.
- Environmental Respect: Appreciate the community’s strong commitment to preserving the natural beauty by practicing responsible outdoor activities and conservation efforts.
Frequently Asked Questions About Bearsville?
1. What are the top vacation rentals in Bearsville?
There are a lot of options in Bearsville. If you plan on staying in the Bearsville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Bearsville:
- Village Center: Gracious & Spacious Retreat "Above the Books"
- Woodstock mountainside retreat, nicest view in the Catskills! RELAX!
- TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
- Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!
- Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
- A True Gem in the heart of Woodstock, w/fireplace & hot tub, wheelchair access
- TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
- Blue View House
- Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
- HOT TUB w/POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
2. How many vacation rentals have private pools in Bearsville?
There are 20 vacation rentals with private pools near Bearsville. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Bearsville are best for families?
If you are looking for a family-friendly vacation home in Bearsville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Bearsville:
4. How many Rentbyowner vacation rentals are available in Bearsville?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 210 in the Bearsville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Bearsville.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the property owner. You should review the specific listing details or contact the host directly to understand the terms before booking.
6. How do I inquire about availability and rates for a vacation rental here?
You can check real-time availability and get rate information by visiting the listing page and reaching out to the property owner if needed for more details.
7. Are there any additional fees or deposits when booking a vacation rental in this destination?
Additional fees, such as cleaning or security deposits, are specified in each listing. Confirm these details with the host prior to finalizing your reservation.
8. What amenities are typically included in vacation rentals around here?
Most properties offer essential amenities like a fully equipped kitchen, Wi-Fi, and parking. To find out about specific amenities, review the listing details or ask the owner directly.
9. Is there a minimum stay requirement for booking a property in this region?
Minimum stay requirements vary by property. Check the individual listing for specific stay durations or contact the owner for clarification.
Bearsville Top Rated Vacation Rentals
House
10.0(123 Reviews)
3 Bedrooms
3 Baths
6 Guests
2100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£638/Night
7 Nights - £4,467
Cottage
10.0(73 Reviews)
4 Bedrooms
2 Baths
8 Guests
2000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£632/Night
7 Nights - £4,421
House
10.0(35 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£612/Night
7 Nights - £4,282
Other
10.0(14 Reviews)
3 Bedrooms
2 Baths
6 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£139/Night
7 Nights - £970
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£430/Night
7 Nights - £3,012
Hotel
9.8(206 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
£132/Night
7 Nights - £925
House
9.8(103 Reviews)
4 Bedrooms
2 Baths
9 Guests
1800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£555/Night
7 Nights - £3,885
House
9.8(78 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£462/Night
7 Nights - £3,234
