Bearsville holiday rentals

We found 412 holiday rentals — enter your dates for availability
Discover a selection of 18 homes and other holiday rentals in Bearsville that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Bearsville

Showing deals for:18 Dec - 25 Dec

A beautiful spot for our comfortable cabin
Rear Deck, Hot Tub and Screened Porch
Property grounds
Open kitchen.
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
AU$4,328
for 7 nights, 1 cabin
AU$618 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Dining
Terrace/patio
Exterior
Living area
Exceptional
(31 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
AU$2,609
for 7 nights, 1 cabin
AU$373 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Living area
Exterior
Private kitchen
Pool
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
AU$4,587
for 7 nights, 1 home
AU$655 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Exterior detail
Property grounds
Living area
Living area
Exceptional
(13 reviews)

"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres

Mount Tremper

12% off
AU$8,726
for 7 nights, 1 home
AU$1,247 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
stay warm & cozy by the fireplace with large screen TV above
Sit stream side and enjoy the beauty of nature and our (seasonal) fire pit
new, beautiful, fully equipped, large, custom kitchen-plenty of counter space.
bluestone, more shaded patio with shade garden
Exceptional
(163 reviews)

Sanctuary by the Stream

Phoenicia

13% off
AU$2,883
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Sanctuary by the Stream
In winter, stay toasty warm by the fire
Welcome to Bridge House
Cooking is a breeze in this recently remodeled kitchen
Large sliders bring nature indoors
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
AU$3,508
for 7 nights, 1 home
AU$501 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Property grounds
Property grounds
Property grounds
Room
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,273
for 7 nights, 1 unit
AU$325 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Exterior
Private kitchen
Great room featuring a wonderful wall of windows
Kitchen with everything you'll need
Exceptional
(52 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off
AU$5,964
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres
Living area
Exterior
Dining
Property grounds
Exceptional
(10 reviews)

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Lake Hill

8% off
AU$2,997
for 7 nights, 1 cabin
AU$428 per night
includes taxes & fees
Most Charming, Most quiet place in the Catskills--Willow-brook Cottage
Children’s area
Screened-in porch with woodland views, elegant seating & peaceful ambiance.
Interior
Relax in our screened-in porch surrounded by forest views and sounds of nature.
Wonderful
(7 reviews)

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

Woodstock

16% off
AU$4,020
for 7 nights, 1 cottage
AU$574 per night
includes taxes & fees
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
One side of romantic master bedroom with pink chaise and king size bed.
View #1 of deck with mountain in background
Third view of LR with woodstove
Side view of house and deck
Exceptional
(46 reviews)

Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream

Phoenicia

8% off
AU$3,385
for 7 nights, 1 home
AU$484 per night
includes taxes & fees
Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream
Property grounds
Living area
Interior
Interior
Exceptional
(26 reviews)

Incredible Lake House with Stunning Mountain Views (swimming lake)

Chichester

8% off
AU$5,648
for 7 nights, 1 home
AU$807 per night
includes taxes & fees
Incredible Lake House with Stunning Mountain Views (swimming lake)
Huge back deck overlooking the creek perfect for relaxing and entertaining.
Exterior
Living room with large dining bar
Living room with large dining bar
Exceptional
(13 reviews)

Magical Waterfront Escape from the city located in the Hudson Valley!

Lake Katrine

8% off
AU$4,645
for 7 nights, 1 home
AU$664 per night
includes taxes & fees
Magical Waterfront Escape from the city located in the Hudson Valley!
Living area
Exterior
Exterior
Dining
Exceptional
(7 reviews)

Charming 3-bedroom bungalow with AC in Phoenicia, Catskills

Phoenicia

8% off
AU$3,803
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
Charming 3-bedroom bungalow with AC in Phoenicia, Catskills
Pool is open Memorial Day through Labor Day.
Covered 15' picnic table for enjoying meals al fresco.
11 ft dining table seats 10-14 people
Distinctive and Charming Chalet in the midst of the Catskills
Exceptional
(7 reviews)

Experience the Catskills - Explore, Entertain and Relax at our Chalet.

Lanesville

16% off
AU$4,048
for 7 nights, 1 home
AU$578 per night
includes taxes & fees
Experience the Catskills - Explore, Entertain and Relax at our Chalet.
Bathroom
Living area
Interior
Room
Exceptional
(43 reviews)

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Phoenicia

17% off
AU$1,868
for 7 nights, 1 apartment
AU$267 per night
includes taxes & fees
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Bearsville getaway

Learn about the unique charm of Bearsville with a stay in a holiday home rental. 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

Do you want to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Bearsville has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Indian Head Mountain (7 mi / 11.3 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (10.7 mi / 17.2 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)

Exploring the natural features in Bearsville

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Bearsville is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • 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)

Transport 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 centre.

Frequently asked questions

What is the best area to stay in Bearsville when booking a holiday rental?
In Bearsville, New York, a charming area located near the vibrant town of Woodstock, you'll find a delightful selection of holiday rentals that cater to various tastes and preferences. One of the best areas to consider is the vicinity around the famous Bearsville Theatre, which not only offers a unique cultural experience with live music and events but also provides easy access to the scenic beauty of the surrounding Catskill Mountains.Staying near the theatre puts you in close proximity to some lovely attractions, including the picturesque Overlook Mountain, which boasts stunning hiking trails and breathtaking views. The nearby Woodstock area is renowned for its artistic vibe, with numerous galleries, shops, and eateries that showcase local talent and cuisine.In terms of available properties, the Bearsville area offers a variety of charming cottages and spacious homes, making it an appealing choice for families or couples seeking a peaceful retreat.
Where are the best Bearsville ski resort rentals?
For those seeking ski resort rentals near Bearsville, the nearby area of Hunter Mountain is a prime destination, located just a short drive away. Visitors can find a variety of holiday rentals in the town of Hunter, which offers convenient access to the ski slopes. These accommodations typically include spacious cabins and lodges, many of which boast amenities such as hot tubs, fireplaces, and fully equipped kitchens, superb for unwinding after a day on the mountain.The surrounding Catskill region is also home to charming properties in areas like Tannersville, where you can discover lovely cottages and mountain homes that often feature stunning views of the surrounding landscape. Many of these rentals provide outdoor spaces, such as decks and patios, where guests can relax and enjoy the scenery, along with convenient access to local hiking trails.In addition to skiing, the Catskills offer a wealth of outdoor activities, including snowshoeing and winter hiking, making this a versatile destination for travel enthusiasts. Rentals in Bearsville itself may include quaint homes with rustic charm, equipped with modern conveniences like Wi-Fi and heating, ensuring a comfortable stay while enjoying the area's winter sports and natural beauty.
What is the most popular type of holiday rental accomodation in Bearsville?
In Bearsville, holiday houses are the most popular type of holiday rental, with approximately 52 available throughout the area. These spacious properties often come with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them superb for families or groups. Many of these homes also feature outdoor spaces such as decks or gardens, where guests can enjoy the natural surroundings of the Catskill Mountains. Additionally, there are around 16 cabins and 16 cottages available, providing a more rustic charm for those looking to immerse themselves in nature.
Are there any family house rentals in Bearsville?
In Bearsville, New York, there are numerous family-friendly house rentals available—specifically, around 17 options to choose from. This charming area is known for its scenic beauty and proximity to a variety of outdoor activities, making it an ideal spot for families. Many properties feature spacious living areas, fully equipped kitchens great for preparing meals, and outdoor spaces for children to enjoy.Visitors can explore nearby attractions such as the renowned Woodstock and the picturesque landscapes of the Catskill Mountains, which offer hiking trails and opportunities for adventure. Additionally, some homes come with amenities like game rooms, private patios, and even fireplaces, enhancing the family experience.
Can I rent a holiday home with a pool or hot tub in Bearsville?
In Bearsville, New York, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation. This quaint area is located in the scenic Hudson Valley, providing a serene backdrop for a getaway. Many of the available properties include amenities such as private swimming pools, luxurious hot tubs, and outdoor living spaces, great for enjoying the natural surroundings. Additionally, travellers can expect fully equipped kitchens and spacious living areas, creating a comfortable home-away-from-home experience.
Are there pet-friendly house rentals in Bearsville?
In Bearsville, there are several pet-friendly house rentals available, with a total of twelve options to choose from. Many of these holiday homes are equipped with amenities that cater to both guests and their furry companions, such as spacious backyards, outdoor seating areas, and fully equipped kitchens.The area is known for its scenic beauty, with opportunities for outdoor exploration and recreation. Nearby, the picturesque Catskill Mountains offer numerous hiking trails that are great for dog walking, and the tranquil surroundings provide a peaceful retreat for both pets and their owners. Additionally, Bearsville's close proximity to the vibrant town of Woodstock means that guests can enjoy local shops, cafes, and restaurants that often welcome pets.
Are there any remote work holiday rentals in Bearsville?
In Bearsville, New York, there are numerous remote work holiday rentals available, with around 88 options to choose from. This charming area, known for its beautiful natural surroundings and artistic vibe, offers a variety of properties suitable for those looking to combine work and leisure. Many of these rentals come equipped with essential amenities such as high-speed internet, Wi-Fi, and dedicated workspaces, making them ideal for remote professionals.Travellers can expect comfortable accommodations that often feature spacious living areas, fully equipped kitchens, and outdoor spaces to unwind after a day of work. The neighbourhood itself is close to various points of interest, including scenic hiking trails and local arts venues, providing a great balance of productivity and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Bearsville?
In Bearsville, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature inviting decks or patios, providing a lovely space to relax outdoors and enjoy the natural surroundings. A fireplace is a common addition, offering a cosy atmosphere for cooler evenings. Additionally, rentals often come with coffee and tea makers, ensuring that guests can start their day with a warm beverage.
When is the best time to visit Bearsville for a holiday rental?
The best time to visit Bearsville for a holiday rental is during the peak season from July to September. This vibrant period attracts travellers seeking a mix of outdoor adventure and cultural experiences, making it an ideal choice for those who appreciate quality and convenience. The warm summer months provide great conditions for exploring the stunning natural beauty of the Catskills, with temperatures typically ranging from 15 to 25 degrees Celsius.September, in particular, is a highlight for visitors. The weather remains pleasantly warm while it's less busy, allowing for a more relaxed experience. This month is great for hiking, enjoying scenic drives, and immersing yourself in the local arts scene. You can also partake in the harvest season, with plenty of opportunities to visit local farms and markets.For those looking to save a bit while still enjoying the charm of Bearsville, November presents an excellent alternative. Although this month marks the low season, it offers a unique opportunity to witness the tranquil beauty of the area as the leaves fall and the landscape prepares for winter. It's a wonderful time for peaceful retreats, great for those who prefer a quieter atmosphere away from the busier months.
What are the top attractions in Bearsville?
In Bearsville, New York, visitors can enjoy a range of attractions that highlight the area's natural beauty and artistic charm. One of the key points of interest is the iconic Bearsville Theater, which hosts a variety of live music and events, making it a cultural hub in the region. The surrounding area is also known for its picturesque landscapes, with opportunities for hiking and exploring the stunning Catskill Mountains nearby.For those interested in art, the nearby town of Woodstock features numerous galleries and studios, showcasing local artists and craftspeople. The charming streets of Woodstock are lined with quaint shops and cafés, offering a superb place to relax and soak in the artistic experience.Nature enthusiasts can take advantage of the proximity to the Ashokan Reservoir, which provides scenic views and recreational activities such as hiking and birdwatching.
Are all fees included in the Bearsville holiday homes prices shown on Stayz?
Stayz 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.
Are there any Bearsville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bearsville 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 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.
Are there any discounts for Bearsville holiday homes?
You can find great discounts on holiday homes in Bearsville on Stayz, 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.
Can I change or cancel my Bearsville holiday home booking on Stayz?
To find Bearsville holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bearsville?
A long-stay holiday home in Bearsville 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Bearsville holiday home?
Book your Bearsville holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bearsville?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bearsville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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