Cheshire Inns | Expedia.ca

A lake surrounded by autumn-colored trees and hills.

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

Next weekend

In two weeks

In one month

In two months

Our top choices for Cheshire inns

1. Gregory House Country Inn

Averill Park

Raghvendra

CA $175 total

includes taxes & fees

Aug 23 - Aug 24

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Breakfast was delayed but the late arriving staff worked quickly to restore it. Quality of food was excellent"

Berkshire Mountain Lodge

8/10 Good

"We would come back here, even though there are quirky aspects to it that make it less than ideal. Overall, it's a good spot that seems like it was built in the fifties (has an old school vibe of a classic lodge), though it's only 20 years old.. What we liked: super clean, very spacious, a full kitchen, a comfortable bed, free parking, and a relatively reasonable rate. What needs improvement: We requested a quiet room and were put on the side where there is a noisy street. It was ok with earplugs. There is no housekeeping during the stay, which was fine for 3 nights, but would get old for longer. The door between the bedroom and living room needs to be fixed and didn't close fully. The toilet made a loud, running noise for 2 minutes with each flush. The handle on the fridge door broke off with normal use. We reported all of these, and none were addressed while we were there. The staff said they would send maintenance, but didn't, and didn't mention that they couldn't fix these items. Finally, we were charged a $22 resort fee that was supposed to include coffee. While they have a lovely espresso machine, no decaf was offered. As mentioned, even with the minor drawbacks, and knowing that it's more of a time share kind of place, where there's no sort of concierge service, it has many positive qualities that make it an overall good spot."

Jiminy Peak Mountain Resort

8/10 Good

"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good

"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Find out more about Cheshire

Cheshire Inns information

Number of reviews
Accommodation	Inns
Lowest Price
Highest Price

Explore a world of travel with Expedia

Dalton Vacation Rentals

Book Inns in Cheshire on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire inns

1. Gregory House Country Inn

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

The Yankee Inn

Berkshires Untold

Jiminy Peak Mountain Resort

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Lee - Lenox South

Find out more about Cheshire

Cheshire Inns information

Explore a world of travel with Expedia

Search Inns in Cheshire

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire inns

1. Gregory House Country Inn

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Cheshire

Cheshire Inns information

Explore a world of travel with Expedia