Book Cheap Hotels in Cheshire

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Most frequently booked Cheshire hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
10.45 km from city centre
The price is CA $138 per night
CA $138
CA $169 total
Oct 20 - Oct 21
includes taxes & fees
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 in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
18.58 km from city centre
The price is CA $150 per night
CA $150
CA $198 total
Oct 1 - Oct 2
includes taxes & fees
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 our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
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
Reserve now, pay when you stay
33.29 km from city centre
The price is CA $181 per night
CA $181
CA $221 total
Oct 2 - Oct 3
includes taxes & fees
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 in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
21.55 km from city centre
The price is CA $178 per night
CA $178
CA $198 total
Oct 1 - Oct 2
includes taxes & fees
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 reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
33.43 km from city centre
The price is CA $229 per night
CA $229
CA $319 total
Oct 31 - Nov 1
includes taxes & fees
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 condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
16.77 km from city centre
The price is CA $310 per night
CA $310
CA $347 total
Oct 29 - Oct 30
includes taxes & fees
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 reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.
Pet-friendly
Parking included
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 centre
The price is CA $202 per night
CA $202
CA $225 total
Oct 29 - Oct 30
includes taxes & fees
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 in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub
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 centre
The price is CA $160 per night
CA $160
CA $178 total
Oct 27 - Oct 28
includes taxes & fees
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 attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly
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
Reserve now, pay when you stay
14.75 km from city centre
The price is CA $136 per night
CA $136
CA $152 total
Oct 31 - Nov 1
includes taxes & fees
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 the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
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See all available properties in Cheshire
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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

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

Hancock
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
1,007 hotels
Lowest Price
CA $152
Highest Price
CA $347
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold, The Red Lion Inn, The Williams Inn, Hotel Downstreet, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 $152 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 1,007 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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"This weekend trip to the Berkshires was made perfect by our wonderful stay at the Black Swan. The property was beautiful and they were wonderfully accommodating to us with our dog. My only regret is that I was not able to try the onsite restaurant. Definitely next time! "
A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Types of hotels

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Areas of Cheshire