A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire 5 Star Hotels

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep
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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
AED 888
AED 991 total
14 Sep - 15 Sep
includes taxes & fees
9.6/10 Exceptional! (658 reviews)
The Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA
AED 368
AED 411 total
1 Sep - 2 Sep
includes taxes & fees
8.4/10 Very Good! (395 reviews)
The Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

30 East Street Stockbridge MA
AED 1,385
AED 1,624 total
13 Sep - 14 Sep
includes taxes & fees
The Inn at Stockbridge
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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 lake views.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Cheshire?
You'll find many different pricing options for a 5-star hotel in Cheshire on Expedia. How much you'll pay will depend on when you plan to travel, length of stay and other factors. Compare available accommodations for your chosen dates and make use of our pricing and other filters to land the ideal upscale stay.
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What makes a hotel 5 stars in Cheshire?
In Cheshire, a hotel must provide a certain amount of high-end amenities to be rated 5 stars. These can include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their superior standard of service. You'll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may even offer extra touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Cheshire?
Use our convenient filters to find a luxurious getaway in Cheshire where everything you need is included. Next, refine your results for resorts that have 5 stars and are categorized as "All inclusive." The first thing on the itinerary at these stays? Pure relaxation and indulgence.

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