
Holiday rentals in Bearsville, Woodstock
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Top-rated holiday rentals in Bearsville, Woodstock
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Bearsville, Woodstock
Superhost

Home in Bearsville
4.83 out of 5 average rating, 54 reviewsMagical Woodstock Getaway
LucyRating, 5 stars2 weeks ago
Bear’s place is awesome! She was very accommodating as we had some last-minute changes to our plan and she was kind enough to be flexible. The home is on a beautiful plot and the cluster of bars & restaurants was a ridiculously convenient 3min walk away. Which is especially awesome since the home itself still feels very private and peaceful! Would definitely recommend to others
Top guest favourite

Home in Woodstock
5 out of 5 average rating, 39 reviewsWoodstock Carriage House
RobertRating, 5 stars3 weeks ago
We had such a great time at the lovely Woodstock carriage house. Everything was clean and as described. It's extremely close to town and provided us a wonderful experience of Woodstock. We felt right at home and the s'mores were such a fun and caring touch! Also, the bed is fantastically comfortable!
Top guest favourite

Barn in Bearsville
5 out of 5 average rating, 8 reviewsFeatured in Vogue! Historic Barn Experience & Pool
AlexRating, 5 stars1 month ago
What a beautiful home! From the minute we walked in we knew we had made a great choice for our weekend getaway from the city. Such an inviting open space with tons of character that gave us the Catskills feel we were after. Shane was super responsive, informative, and friendly. Would absolutely recommend to anyone looking for a peaceful retreat.
Guest favourite

Home in Bearsville
4.94 out of 5 average rating, 52 reviewsWoodstock Ski House 35 Private acres w Moutn Views
LaurenRating, 5 stars1 month ago
Everything was very comfortable and stress-free. The grounds are beautiful and we loved the location. We look forward to staying there again!
Guest favourite

Home in Woodstock
4.96 out of 5 average rating, 224 reviewsGrandma's Place an Easy Walk to Woodstock
JadeRating, 5 stars3 days ago
We loved staying at Grandmas place. It’s such a lovely home and the back yard is so beautiful. It’s very close to town and we walked everywhere. The kitchen is fully stocked, there is a fire pit out back, and the beds are comfy. Grandma does live there and stays on the adjoining right side of the house but we still felt it was quite private and fully had the space to ourselves during our stay. We would stay again and Woodstock is filled with fun things to do and great places to eat.
Top guest favourite

Home in Woodstock
4.98 out of 5 average rating, 42 reviewsFiber Artist's Studio
ChantalRating, 5 stars1 month ago
Peter was the epitome of charm complete with gentle personable humour. The place itself was above our expectations as we really loved how utterly peaceful it is. Moreover, the enormous panoramic window in the master bedroom was the crowning glory as the view is stunning. A totally tranquil retreat with easy access to Woodstock and great hiking trails and more. Highly recommended. Thank you again Peter- we loved it.
Guest favourite

Home in Bearsville
4.86 out of 5 average rating, 49 reviewsSpacious Private Retreat w. Pool + Fireplace
JacquelineRating, 5 stars2 weeks ago
A spacious home, true to the listing photos, great natural light, great location, easy drive to Woodstock restaurants & shops and hikes. Meghan was responsive, friendly, and provided great local recommendations. Note, when we stayed there were no window treatments on any of the windows in the house, including the bedrooms.
Top guest favourite

Guest suite in West Shokan
4.95 out of 5 average rating, 131 reviewsStylish and Cozy Mountain Retreat
lynnRating, 5 stars1 week ago
Beautiful little spot for an overnight stay. Had everything you need and was very comfortable.
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Windham Mountain
- Resorts World Catskills
- Albany Center Gallery
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Zoom Flume
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Hunter Mountain Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hancock Shaker Village