A lake surrounded by autumn-colored trees and hills.

Preferred Cheshire hotels

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Check prices for these dates

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

Our top choices for Cheshire Preferred

1. The Orchards Hotel

The Orchards Hotel
Williamstown
United States
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The Orchards Hotel
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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 13 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 23 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 1 day 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 1 day 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

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