Cherry Plain Hotels

Start date: Check-in selected.
To Date
End date: Check-out

    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

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Cherry Plain hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (746)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is P5,064
P5,656 total
includes taxes & fees
Nov 4 - Nov 5
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great location, very clean!"
The price is P7,760
P8,668 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1004)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is P7,389
P10,516 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (893)
"Excellent customer service and great rooms"
The price is P6,010
P6,713 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (677)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is P5,173
P7,082 total
includes taxes & fees
Oct 19 - Oct 20
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (51)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is P7,390
P8,255 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2041)
"Extended stay since resort was so beautiful"
The price is P5,308
P6,564 total
includes taxes & fees
Nov 2 - Nov 3
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is P8,116
P9,066 total
includes taxes & fees
Nov 5 - Nov 6
Hotel Downstreet, an Ascend Collection Hotel
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is P5,671
P6,335 total
includes taxes & fees
Oct 8 - Oct 9
Huttopia Berkshires
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is P7,060
P7,887 total
includes taxes & fees
Nov 3 - Nov 4
Hotel On North
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (303)
"The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind."
The price is P4,610
P5,149 total
includes taxes & fees
Nov 2 - Nov 3
Williamstown Motel
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Great property would certainly stay again."
The price is P5,933
P6,627 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Berkshire Hills Inn & Suites
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.6 out of 10, (884)
"Great affordable place to stay while in the northern Berkshires."
The price is P6,365
P7,110 total
includes taxes & fees
Oct 8 - Oct 9
Howard Johnson by Wyndham Williamstown
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (788)
"Good service and people"
The price is P4,635
P5,178 total
includes taxes & fees
Oct 20 - Oct 21
FairBridge Inn Express
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (747)
"Perfect location for our passing through vacay."
The price is P4,572
P5,106 total
includes taxes & fees
Nov 2 - Nov 3
The Villager Motel
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (515)
"Nice place to stay for a wedding "
The price is P12,248
P13,681 total
includes taxes & fees
Nov 5 - Nov 6
The Williams Inn
Comfort Inn & Suites East Greenbush - Albany
Lobby

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
8.4 out of 10, Very Good, (1003)
"Clean room and great staff"
The price is P6,345
P7,044 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites East Greenbush - Albany
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (322)
"Nice place "
The price is P5,718
P6,387 total
includes taxes & fees
Oct 31 - Nov 1
The Central Downtown Inn & Suites
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (805)
"Great place to stay for overnight stays. Breakfast was appreciated."
The price is P4,572
P5,106 total
includes taxes & fees
Oct 20 - Oct 21
Howard Johnson by Wyndham Lenox
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (384)
"our stay was great."
The price is P8,796
P9,825 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Williamstown
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy 2-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

More cheap stays in Cherry Plain

More cheap stays in Cherry Plain

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is P4,572 per night from Oct 20 to Oct 21
P4,572
P5,106 total
Oct 20 - Oct 21
includes taxes & fees
7.4/10 Good! (802 reviews)

Frequently asked questions

Where is the best place to stay in Cherry Plain?

Vacation Village in the Berkshires, located 5.6 mi (9 km) from the heart of Cherry Plain, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Cherry Plain.

If I need to cancel my hotel reservation in Cherry Plain, will I receive a refund?

Yes! Most room reservations are refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cherry Plain.

Where can I learn more about changing or cancelling my trip to Cherry Plain?

To access more information about rescheduling or cancelling your trip to Cherry Plain, go to https://www.expedia.com/service/.

What is staying in Cherry Plain like?

Visitors to Cherry Plain are sure to find plenty to explore and enjoy. There are 677 hotels and other accommodations in the surrounding area. Find out more about Cherry Plain.

What should I see while I'm in Cherry Plain?

Places to visit in the wider area include Brodie Mountain, Williamstown Theatre Festival, and Jiminy Peak Mountain Resort. You'll also find Mountain Coaster and Waubeeka Golf Links in the area. Check out what more to see and do in Expedia's Cherry Plain guide.

What's the weather like in Cherry Plain?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cherry Plain are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia

Explore a world of travel with Expedia