Book Cheap Hotels in Cheshire

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Most frequently booked Cheshire hotels

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

18.58 km from city centre

CA $121

CA $165 total

May 24 - May 25

includes taxes & fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Pool

Hot tub

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

21.55 km from city centre

CA $147

CA $165 total

May 20 - May 21

includes taxes & fees

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

Pet-friendly

Parking included

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free cancellation

Reserve now, pay when you stay

10.45 km from city centre

CA $118

CA $147 total

May 20 - May 21

includes taxes & fees

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Pool

Parking included

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free cancellation

15.74 km from city centre

CA $209

CA $233 total

May 25 - May 26

includes taxes & fees

Book a stay at this business-friendly 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 in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.

Pool

Hot tub

The Red Lion Inn

30 Main Street Stockbridge MA

Free cancellation

Reserve now, pay when you stay

33.43 km from city centre

CA $215

CA $302 total

May 28 - May 29

includes taxes & fees

Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.

Pool

Spa

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

19.83 km from city centre

CA $164

CA $183 total

May 25 - May 26

includes taxes & fees

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 helpful staff in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Pool

Breakfast included

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

190 Meadow Street South Lee MA

Free cancellation

33.29 km from city centre

CA $160

CA $205 total

May 25 - May 26

includes taxes & fees

Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.

Pool

Air conditioning

The Black Swan Lee - Lenox, an Ascend Collection Hotel

435 Laurel St Lee MA

Free cancellation

27.9 km from city centre

CA $173

CA $193 total

May 27 - May 28

includes taxes & fees

Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.

Breakfast included

Pet-friendly

The Williams Inn

101 Spring Street Williamstown MA

Free cancellation

Reserve now, pay when you stay

16.77 km from city centre

CA $346

CA $386 total

May 26 - May 27

includes taxes & fees

Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.

Pet-friendly

Parking included

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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.

Top hotels in Cheshire for Extended Stay

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Hancock MA

10/10 Exceptional! (4 reviews)

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.

Cheshire hotels essential information

Accommodation	1,014 hotels
Lowest Price	CA $147
Highest Price	CA $386
Popular hotels	Berkshire Mountain Lodge, Berkshires Untold, Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Williams Inn

Frequently asked questions

What are the top kid-friendly hotels in Cheshire?

Take some of the worries out of traveling with little ones by booking a family-friendly Cheshire hotel. From thoughtful amenities to additional services, these properties feature perks that'll help make your getaway run like a dream: 19th c. Barn in the Berkshires will help make your next trip the most memorable one yet. It features a range of conveniences geared toward families, such as a playground and animal viewing activities. Harbour House Inn is another great choice. After a long day of exploring, return to your comfortable room and amenities like complimentary breakfast and free WiFi.

Where can I find cheap hotels in Cheshire?

At Travelocity you'll find really nice hotels in Cheshire at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Cheshire rather than in Cheshire. We may find you even better rates, too.

How do I find the best Cheshire hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Cheshire then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Cheshire?

The cheapest hotel in Cheshire is CA $147 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Cheshire?

There are 1,014 hotels in Cheshire on Travelocity.

What are the best hotels in Cheshire?

Cheshire has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Cheshire for you!

When is the best time to visit Cheshire?

If you want the joy of a fun-filled trip in peak season, visit Cheshire during June, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.

When is the cheapest time to stay in Cheshire?

Based on historic data is usually the cheapest month to visit Cheshire. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Cheshire?

There are multiple hotels in Cheshire that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Cheshire. We have plenty of kid-friendly hotels in Cheshire to choose from on Travelocity!

Why book a hotel in Cheshire through Travelocity?

Because we have the top hotels in Cheshire! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Cheshire on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Cheshire hotel reviews by fellow wanderers

Berkshire Mountain Lodge

4 out of 5

Posted 3 hours ago

Travelocity Verified Review

"the Kitchen appeared to be fully equiped. The only cpmplaint I have was there were no avaiable plugs for mt CPAP machine nect to the bed> Easy fix is to offit the room with a multi plug on the night table.or lamp with plugs. Also there were no USB charging ports. Otherwise the facility was great "

A verified traveller stayed at Berkshire Mountain Lodge