Skip to content
Some info has been automatically translated. Show original language

Vacation rentals in Cherry Plain

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cherry Plain

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

Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.
$239 per night
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!
$125 per night
Guest suite in Williamstown
Berkshire Guest Suite
Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.
$85 per night

Other great vacation rentals in Cherry Plain

Home in New Lebanon
The old sawmill from 1771
$125 per night
Guest suite in Hancock
Cozy apartment near Jiminy Peak
$80 per night
Apartment in North Adams
Steps to MoCA, 2bd + SAUNA!
$131 per night
Cottage in Shaftsbury
Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
$377 per night
Apartment in Williamstown
$112 per night
Apartment in Williamstown
New Studio In Town, By the Water
$130 per night
Guesthouse in Williamstown
Brookside Cottage
$95 per night
Apartment in Troy
Modern Luxury & Victorian Charm: The Bird in Hand
$77 per night
Condo in Hancock
Cozy Condo @Jiminy Peak
$183 per night
Cabin in Williamstown
Charming Cabin in the Berkshires!
$200 per night
Vacation home in Williamstown
ALL welcome: Lovely 1 BR studio, Berkshires beauty
$150 per night
Cottage in Hancock
Berkshire Cottage Queen Bd-Jiminy Peak 3 mi
$148 per night

Destinations to explore