A lake surrounded by autumn-colored trees and hills.

Compare and book 5 Star hotels in Cheshire, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire 5 Star Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Cheshire.
The Williams Inn

The Williams Inn

101 Spring Street Williamstown MA
£154
28 Sept - 29 Sept
includes taxes & fees
9.6/10 Exceptional! (675 reviews)
The Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA
£82
8 Oct - 9 Oct
includes taxes & fees
The Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

30 East Street Stockbridge MA
£373
23 Sept - 24 Sept
includes taxes & fees
9.6/10 Exceptional! (107 reviews)
The Inn at Stockbridge
Still don't see what you're looking for?
See all properties in Cheshire.
You can also use these popular filters to refine your search.
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.

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and natural setting.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees with a clear sky.

Top Cheshire Hotel Reviews

Find out more about Cheshire

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Cheshire?
How much you pay for a 5-star hotel in Cheshire depends on factors like when you want to go and the length of your getaway. Our insider tip for scoring the best deal? Use our pricing filters to check out the available hotels for your selected dates.
  • Search for the lowest price per night from £82
What makes a hotel 5 stars in Cheshire?
Flawless guest service is integral to every 5-star hotel in Cheshire. From the minute you arrive, staff ensure your every need is met, whether recommending activities and tours or providing in-room massages. In addition, hotels must feature top-rate amenities to obtain a 5-star rating. These can include luxury bath products, an on-site spa, pools, fine dining restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Cheshire?
Find an indulgent stay that includes your room, meals, drinks and entertainment in Cheshire with the help of our filter tool. Search for properties rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the price. This way, you're ready to take advantage of the premium perks on offer when you arrive.

Explore a world of travel with Expedia