2025 Cheshire, Massachusetts Hotels

Up To 10% Off Select Hotels With AARP Member Discounts

Photo by Ed Gaffny

Choose from AARP Discount Cheshire Hotels with Free Cancellation

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
15.79 km from city center
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Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
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10.45 km from city center
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Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
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18.58 km from city center
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Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
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33.29 km from city center
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Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
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33.43 km from city center
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Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
10.84 km from city center
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Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
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21.55 km from city center
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Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
19.64 km from city center
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Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Free Cancellation
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16.77 km from city center
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Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
Free Cancellation
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10.66 km from city center
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Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
19.61 km from city center
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Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
27.9 km from city center
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Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street, Pittsfield, MA
19.05 km from city center
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Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
14.75 km from city center
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Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
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18.74 km from city center
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Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street, North Adams, MA
Free Cancellation
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16.11 km from city center
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Stay at this 3.5-star business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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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.

Your Guide to Cheshire Hotels

AARP® Travel Center Powered by Expedia® can help you get the hotel you want at a great rate, if you are visiting Cheshire. Time for a hard-earned break, or showing your kids and grandkids the area? AARP® Travel Center Powered by Expedia® can assist you in getting the exact hotel you want for a good value. We have a broad variety of hotels to choose between. You can use your membership benefits to schedule an elegant 5-star accommodation, or a hotel that is within vicinity of the sights you want to see. There are plenty of things to do and see in Cheshire, and with us, you will save a ton on your vacation.

Things To Do in Cheshire

In Cheshire, we have lined up 995 hotels that offer reasonable rates through the AARP Travel Center powered by Expedia. Once you check-in to your Cheshire hotel, you can check out all this area has to offer. You can ask your hotel's front desk or click on our "Things To Do" tab if you are unsure where start off your vacation in Cheshire. While you begin setting up your getaway, we can also help you set up some activities. When you book with AARP Travel Center Powered by Expedia, you will spend more time making the most out of your trip, no matter where you decide to travel.

Reserve Your Hotel with the AARP Travel Center Today

We will make it easy for you to book your next hotel stay. Whether you are coming to Cheshire for business or to relax, we are going to make sure that you get the greatest deals available. When you are ready to check out Cheshire's appeals, like an and , we'll help you get everything booked for you and your grand kids. Luckily, with our great travel deals, you won't have to worry about breaking the bank to have a fun getaway. You may find that booking through AARP gives you the best deals. You will have peace of mind during your entire vacation. Why? You scored the best deal possible. Book with AARP, and both you and your wallet will be pleased that you are taking this vacation.