Cherry Plain Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Cherry Plain vacation rentals

Exterior

Vacation Home in Pownal

Cozy Home in Pownal VT
The price is ￥16,068
￥31,076 total
includes taxes & fees
Jan 27 - Jan 28
Cozy Home in Pownal VT
Lobby

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,219 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,188
￥19,790 total
includes taxes & fees
Jan 27 - Jan 28
Vacation Village in the Berkshires
Exterior

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥34,098
￥38,088 total
includes taxes & fees
Jan 27 - Jan 28
Jiminy Peak Mountain Resort
TV

Vacation Home in Florida

Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥28,610
￥53,109 total
includes taxes & fees
Jan 27 - Jan 28
Florida Mountain Log Cabin
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (8 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥29,639
￥33,107 total
includes taxes & fees
Feb 1 - Feb 2
Huttopia Berkshires
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is ￥21,331
￥42,958 total
includes taxes & fees
Jan 27 - Jan 28
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥25,223
￥65,394 total
includes taxes & fees
Jan 27 - Jan 28
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
WiFi, bed sheets

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is ￥21,020
￥32,325 total
includes taxes & fees
Jan 27 - Jan 28
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor dining

Apartment in Williamstown

2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (11 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is ￥18,684
￥44,128 total
includes taxes & fees
Jan 29 - Jan 30
2-Bdr Apt In Town, By the Water
Outdoor dining

Apartment in Williamstown

Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is ￥20,241
￥45,011 total
includes taxes & fees
Feb 18 - Feb 19
Downtown | Waterfront | Walk to Shops
Outdoor dining

Apartment in Williamstown

New Studio In Town, By the Water
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ￥18,684
￥42,014 total
includes taxes & fees
Jan 27 - Jan 28
New Studio In Town, By the Water
Exterior

Cabin in Sand Lake

Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (13 reviews)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is ￥19,463
￥28,517 total
includes taxes & fees
Jan 27 - Jan 28
Taborton Harvest Boulder Pines Cabin in the woods
Living area

Apartment in Adams

Penthouse Apartment on Park Street
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is ￥22,577
￥43,827 total
includes taxes & fees
Jan 29 - Jan 30
Penthouse Apartment on Park Street
House (3 Bedrooms) | Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is ￥30,517
￥86,200 total
includes taxes & fees
Jan 27 - Jan 28
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Fridge, microwave, stovetop, dishwasher

Vacation Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,248
￥87,714 total
includes taxes & fees
Jan 27 - Jan 28
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (28 reviews)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is ￥10,510
￥22,236 total
includes taxes & fees
Jan 27 - Jan 28
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

Apartment in North Adams

The Allen House historic North Adams Home in the Berkshire Mountains
10.0 out of 10, Exceptional, (1 review)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
The price is ￥27,248
￥48,176 total
includes taxes & fees
Feb 24 - Feb 25
The Allen House historic North Adams Home in the Berkshire Mountains
Exterior

Vacation Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
The price is ￥36,784
￥63,376 total
includes taxes & fees
Feb 17 - Feb 18
The Greylock Cabin
Beach

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥14,994
￥33,245 total
includes taxes & fees
Jan 27 - Jan 28
Berkshires Apartment at the Stephentown Hotel
Outdoor dining

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,523
￥50,726 total
includes taxes & fees
Jan 29 - Jan 30
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cherry Plain Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Beautiful unique property! Very clean room and very friendly staff"
Iolanda 1-night trip
Posted 4 days ago
Berkshires Untold

Find out more about Cherry Plain

Search for holiday rentals in Cherry Plain on Expedia! You can easily find your home rentals, villas, holiday apartments in Cherry Plain using one of the methods below:

  • View our selection of featured holiday rentals in Cherry Plain
  • Use the map to find apartments and other holiday homes in the Cherry Plain neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cherry Plain while they last

Look no further and take a look at our great range of rental properties in Cherry Plain!

Frequently asked questions

Can I find a vacation rental in Cherry Plain?

Yes, you can find vacation rentals near well known local attractions in Cherry Plain, or you can choose a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Cherry Plain has to offer?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Cherry Plain offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What can I see and do in Cherry Plain?

Explore the area and family-friendly sights such as Zema's Nursery, or get out into nature at a spot like Brodie Mountain. Williamstown Theatre Festival and Jiminy Peak Mountain Resort are a couple of places you'll find in the larger area.

What are vacation rentals like in Cherry Plain?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Cherry Plain. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.