Vacation rentals in Bear Mountain

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Top-rated vacation rentals in Bear Mountain

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

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

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!

Sep 14 – 21

G$22,386 GYD per night
Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 318 reviews

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.

Jun 18 – 25

G$34,487 GYD per night
Guest favorite

Apartment in Canaan

4.98 out of 5 average rating, 102 reviews

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Apr 28 – May 5

G$27,487 GYD per night

Popular amenities for Bear Mountain vacation rentals

Other great vacation rentals in Bear Mountain

Guest favorite

Cabin in Ancram

5.0 out of 5 average rating, 115 reviews

The Ancram A - Luxury Mid-Century Modern Cabin

Aug 19 – 26

G$79,394 GYD per night
Superhost

Cabin in Sheffield

4.81 out of 5 average rating, 246 reviews

Log Cabin - playroom, fireplace, skiing - $0 fees

Aug 31 – Sep 7

G$95,093 GYD per night
Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 100 reviews

Cheerful 3-bedroom cottage with woodstove.

Nov 17 – 24

G$57,730 GYD per night
Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 217 reviews

Gorgeous Tiny House with Mountain View

Sep 20 – 27

G$25,618 GYD per night
Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Sep 13 – 20

G$32,097 GYD per night
Guest favorite

Home in Millerton

4.95 out of 5 average rating, 110 reviews

Vacation Home In Millerton

Nov 17 – 24

G$39,923 GYD per night
Guest favorite

Treehouse in Willow

4.96 out of 5 average rating, 703 reviews

Willow Treehouse - secluded, unique, romantic

Jan 28 – Feb 4

G$91,866 GYD per night
Guest favorite

Earthen home in West Sand Lake

4.98 out of 5 average rating, 147 reviews

The Hobbit House at June Farms

Dec 17 – 24

G$72,760 GYD per night
Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Apr 5 – 12

G$33,611 GYD per night
Guest favorite

Cottage in Red Hook

4.98 out of 5 average rating, 590 reviews

bright serene + spacious barn

Oct 25 – Nov 1

G$80,554 GYD per night
Guest favorite

Cabin in Kingston

4.98 out of 5 average rating, 332 reviews

Come Stay in "The Shoe"

Nov 14 – 21

G$27,590 GYD per night
Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Apr 17 – 24

G$199,202 GYD per night

Destinations to explore