Over 1,000 places in Cherry Plain

Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
2 beds
Apr 1 – 6
4.85 out of 5 average rating, 143 reviews
Guest favorite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
3 beds
Apr 2 – 7
4.83 out of 5 average rating, 151 reviews
Home in Stephentown
The Home and The Forest
8 beds
Apr 1 – 6
Superhost
Home in Hancock
Bougie B's Mountainside Getaway
2 beds
Apr 1 – 6
New place to stay
Guest favorite
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
1 king bed
Apr 5 – 10
4.9 out of 5 average rating, 51 reviews
Guest favorite
Cottage in Hancock
Berkshire Cottage Queen Bd-Jiminy Peak 3 mi
2 beds
Apr 1 – 6
4.86 out of 5 average rating, 64 reviews
Guest favorite
Vacation home in Williamstown
ALL welcome: Lovely 1 BR studio, Berkshires beauty
1 queen bed
Apr 1 – 6
4.97 out of 5 average rating, 67 reviews
Guest favorite
Home in Berlin
Four Season Retreat
3 beds
Apr 4 – 9
5.0 out of 5 average rating, 60 reviews
Guest favorite
Cottage in Averill Park
Cozy cottage with pool, walking distance to lake
3 beds
Apr 1 – 6
4.98 out of 5 average rating, 89 reviews
Guest favorite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
2 beds
Apr 2 – 7
4.9 out of 5 average rating, 164 reviews
Home in Williamstown
Modern Rustic Cottage- 7 minutes to Jiminy Peak!
4 beds
Apr 1 – 6
New place to stay
Guest favorite
Home in Williamstown
Elegant Mountain View Retreat By Evergreen Home
5 beds
Apr 7 – 12
5.0 out of 5 average rating, 6 reviews
Guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
1 queen bed
Apr 7 – 12
5.0 out of 5 average rating, 355 reviews
Home in Hancock
Home in Hancock A true gem in the Berkshires
4 beds
Apr 1 – 6
Guest favorite
Cabin in Sand Lake
"The Cabin" - Cozy & Rustic Home (Averill Park)
4 beds
Apr 6 – 11
5.0 out of 5 average rating, 19 reviews
Guest favorite
Cabin in Petersburg
Farmhouse Guest Cabin with Mountain Views
3 beds
Apr 1 – 6
4.99 out of 5 average rating, 97 reviews
Guest favorite
Home in Lanesborough
Scenic mountain getaway.
4 beds
Apr 9 – 14
5.0 out of 5 average rating, 46 reviews
Guest favorite
Chalet in Averill Park
A Hidden Sparrow
4 beds
Apr 17 – 22
4.93 out of 5 average rating, 46 reviews