Holiday rentals in Bear Mountain

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Top-rated holiday rentals in Bear Mountain

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Escape to a private acre of forest in the Berkshires near Great Barrington. Our large post and beam log cabin has been updated with all the modern essentials like WiFi, streaming channels, open kitchen, outdoor deck, gym/yoga studio, ping pong table and a screened porch for those beautiful warm evenings. If you have young children, you will love the separate playroom stocked with toys, books and games. For hikers, the AT is 1 hour hike from the front porch. 2:15 from NYC and 2:30 from BOS
16–23 AugProfessional Host,
£466 per night
4.81 out of 5 average rating, 243 reviews
Guest favourite
Flat in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
19–26 AugProfessional Host,
£121 per night
4.93 out of 5 average rating, 246 reviews
Guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.
4–11 OctProfessional Host,
£154 per night
5.0 out of 5 average rating, 317 reviews

Popular amenities for Bear Mountain holiday rentals

Other great holiday rentals in Bear Mountain

Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
9–16 FebIndividual Host,
£353 per night
4.94 out of 5 average rating, 341 reviews
Guest favourite
Treehouse in Willow
Willow Treehouse - secluded, unique, romantic
7–14 FebIndividual Host,
£374 per night
4.96 out of 5 average rating, 696 reviews
Guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
25 Dec – 1 JanIndividual Host,
£139 per night
4.91 out of 5 average rating, 223 reviews
Guest favourite
Home in Millerton
Vacation Home In Millerton
27 Jan – 3 FebIndividual Host,
£160 per night
4.95 out of 5 average rating, 107 reviews
Guest favourite
Treehouse in Catskill
The Hudson Lookout: Watchtower with Views + Sauna
31 Jul – 7 AugIndividual Host,
£345 per night
5.0 out of 5 average rating, 139 reviews
Guest favourite
Cottage in Red Hook
bright serene + spacious barn
31 Jul – 7 AugIndividual Host,
£273 per night
4.98 out of 5 average rating, 586 reviews
Guest favourite
Cottage in Copake Falls
Beautiful cottage in Copake Falls
11–18 MayIndividual Host,
£135 per night
4.9 out of 5 average rating, 312 reviews
Guest favourite
Cabin in Ancram
The Ancram A - Luxury Mid-Century Modern Cabin
13–20 JunIndividual Host,
£328 per night
5.0 out of 5 average rating, 113 reviews
Guest favourite
Barn in Hillsdale
Hudson Valley Hilltop Barn
13–20 AprIndividual Host,
£824 per night
4.97 out of 5 average rating, 115 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
3–10 JunIndividual Host,
£267 per night
5.0 out of 5 average rating, 219 reviews
Guest favourite
Flat in Canaan
West Main
16–23 MarIndividual Host,
£118 per night
4.98 out of 5 average rating, 102 reviews
Guest favourite
Home in Hillsdale
Lake House, Copake Lake, NY
4–11 AprIndividual Host,
£143 per night
4.93 out of 5 average rating, 206 reviews

Destinations to explore