A lake surrounded by autumn-colored trees and hills.

Find all hotels by Preferred in Cheshire, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Cheshire Preferred

A snow-covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by a house with illuminated windows and a tree with lights.
A hotel room with a large bed, a bench, a small table, and framed floral artwork on the wall.
A room with two blue armchairs, a small table with a lamp and vase, and large windows with curtains.
A cozy living room with a fireplace, striped armchairs, a sofa, and a bookshelf filled with books.

1. The Orchards Hotel

The Orchards Hotel
Williamstown
United States
Anonymous traveler
The Orchards Hotel
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Beautiful view. Clean and comfortable. Great breakfast choices"
toan 3-night trip
Posted 9 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Dolores 3-night trip
Posted 19 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 20 hours ago
The Red Lion Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"I really love staying here. It’s no nonsense clean and i feel safe traveling as a woman alone… However they really need to step up their morning breakfast. I eat gluten free and they never have any. I’ve asked for ivermectin a month now and they just tell me they will mention it…."
Lauren 2-night trip
Posted 21 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel On North

Hotel On North

10/10 Excellent
"Great location, clean room!"
Gayle 1-night trip
Posted 2 days ago
Hotel On North
The Whitlock

The Whitlock

10/10 Excellent
"Front desk staff amazing. Very quaint and well maintained building. Room large and free standing tub wonderful. Great location. Good bargin as well."
Dana 1-night trip
Posted 2 days ago
The Whitlock

Explore a world of travel with Expedia