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Check prices in Cheshire for tonight, Aug 25 - Aug 26
Aug 25 - Aug 26
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Check prices in Cheshire for tomorrow night, Aug 26 - Aug 27
Aug 26 - Aug 27
This weekend
Check prices in Cheshire for this weekend, Aug 28 - Aug 30
Aug 28 - Aug 30
Next weekend
Check prices in Cheshire for next weekend, Sep 4 - Sep 6
Sep 4 - Sep 6

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 center
The price is CA $120 per night
CA $120
CA $149 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this family-friendly aparthotel 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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
19.61 km from city center
The price is CA $177 per night
CA $177
CA $198 total
Sep 16 - Sep 17
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 pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
18.58 km from city center
The price is CA $130 per night
CA $130
CA $176 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this golf aparthotel 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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
10.84 km from city center
The price is CA $83 per night
CA $83
CA $93 total
Aug 31 - Sep 1
includes taxes & fees
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 and Crane Museum of Papermaking are located nearby.
Parking included
Free WiFi
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 center
The price is CA $195 per night
CA $195
CA $218 total
Sep 7 - Sep 8
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
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
19.05 km from city center
The price is CA $165 per night
CA $165
CA $184 total
Sep 24 - Sep 25
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
33.43 km from city center
The price is CA $202 per night
CA $202
CA $294 total
Sep 8 - Sep 9
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
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
19.64 km from city center
The price is CA $109 per night
CA $109
CA $122 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this motel in Lenox. Enjoy free parking, a 24-hour front desk, and daily housekeeping. 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
Parking included
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free cancellation
Reserve now, pay when you stay
16.77 km from city center
The price is CA $354 per night
CA $354
CA $396 total
Sep 21 - Sep 22
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
Don't see what you're looking for?
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 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
1,001 hotels
Lowest Price
CA $93
Highest Price
CA $396
Popular hotels
Vacation Village in the Berkshires, The Yankee Inn, Berkshire Mountain Lodge, FairBridge Inn Express, Berkshires Untold, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, The Red Lion Inn, Howard Johnson by Wyndham Lenox, 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 $93 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 1,001 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

Berkshire Mountain Lodge

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Clean room. Nice hotel. Great option in the Lenox area."
A verified traveller stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge