Hotels in Cheshire
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Harbour House Inn
Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
9.4/10
Exceptional
(53)
- Cozy Cheshire B&B within easy reach of Adams Theater and Mount Greylock.
The price is $215
$215
$227 total
includes taxes & fees
Jan 7 - Jan 8
The Springs Motel
The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (89)
9.2/10
Wonderful
(89)
- Cozy lodging near Jiminy Peak offers outdoor relaxation at seasonal pool.
The price is $115
$115
$126 total
includes taxes & fees
Jan 4 - Jan 5
The Revival House
The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
9.0/10
Wonderful
(25)
- Tranquil guesthouse in Adams with free breakfast and easy access to local attractions.
The price is $150
$150
$168 total
includes taxes & fees
Jan 4 - Jan 5
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144)
9.0/10
Wonderful
(144)
The price is $174
$174
$194 total
includes taxes & fees
Jan 4 - Jan 5
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2199)
8.8/10
Excellent
(2199)
The price is $116
$116
$141 total
includes taxes & fees
Jan 4 - Jan 5
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
5.4/10
(811)
- Restful sanctuary in Pittsfield with free WiFi and parking, perfect for skiers.
The price is $89
$89
$99 total
includes taxes & fees
Jan 4 - Jan 5
Berkshire Valley Inn
Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (564)
9.2/10
Wonderful
(564)
- Cozy mountain stay near Jiminy Peak with skiing, pool, and trails for adventurers.
The price is $139
$139
$155 total
includes taxes & fees
Jan 4 - Jan 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1004)
8.0/10
Very Good
(1004)
- Located in Pittsfield, the hotel offers peaceful rooms near Berkshire attractions.
The price is $98
$98
$109 total
includes taxes & fees
Jan 9 - Jan 10
Berkshire Inn
Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
7.8/10
Good
(840)
- Peaceful Berkshire Inn near cultural attractions and outdoor adventures awaits.
The price is $86
$86
$96 total
includes taxes & fees
Jan 19 - Jan 20
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (349)
8.6/10
Excellent
(349)
The price is $94
$94
$105 total
includes taxes & fees
Jan 11 - Jan 12
Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (899)
6.6/10
(899)
- Experience Northern Berkshires with free perks and helpful staff at this motel.
The price is $90
$90
$101 total
includes taxes & fees
Jan 4 - Jan 5
1896 House Country Inn & Motels
1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (448)
6.6/10
(448)
- Peaceful inn nestled among Williamstown attractions with restaurant and bar.
The price is $125
$125
$140 total
includes taxes & fees
Jan 4 - Jan 5
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (988)
8.2/10
Very Good
(988)
- Ski-in/ski-out access at Jiminy Peak offers alpine convenience and mountain thrills.
The price is $219
$219
$245 total
includes taxes & fees
Jan 4 - Jan 5
Hotel On North
Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (809)
9.6/10
Exceptional
(809)
- Experience refined comfort in the heart of Pittsfield, steps from transportation.
The price is $149
$149
$166 total
includes taxes & fees
Jan 4 - Jan 5
Willows Motel Williamstown
Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (997)
9.0/10
Wonderful
(997)
- Scenic Berkshire stay with poolside dining and minutes to Lower Linear Park.
The price is $85
$85
$95 total
includes taxes & fees
Jan 4 - Jan 5
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
10/10
Exceptional
(7)
- In the heart of Williamstown, this campground is a 10-minute drive from Jiminy Peak Mountain Resort.
The price is $203
$203
$226 total
includes taxes & fees
Jan 4 - Jan 5
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1002)
8.8/10
Excellent
(1002)
The price is $116
$116
$130 total
includes taxes & fees
Feb 2 - Feb 3
Maple Terrace Motel
Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (594)
9.6/10
Exceptional
(594)
- Take a relaxing summer dip in the outdoor pool near Lower Linear Park and Williamstown attractions.
The price is $99
$99
$111 total
includes taxes & fees
Jan 4 - Jan 5
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
- Relaxing Berkshire retreat near Tanglewood with free breakfast and mountain recreation.
The price is $76
$76
$85 total
includes taxes & fees
Feb 3 - Feb 4
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (451)
9.4/10
Exceptional
(451)
The price is $144
$144
$183 total
includes taxes & fees
Feb 2 - Feb 3
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.
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.
Go beyond your typical stay in Cheshire
Pet friendly
Family friendly
Cottage
Learn more about Cheshire
The region around Cheshire is home to attractions such as Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center.
Check out reviews of Cheshire hotels guests love
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Clean"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Staff was very pleasant and friendly. From front desk to valet. "
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"friendly accommodating staff"
Berkshire Mountain Lodge
10/10 Excellent
"great stall and friendly pet friendly place"
The Williams Inn
10/10 Excellent
"Clean room | Staff "
Berkshires Untold
10/10 Excellent
"Great hospitality and beautiful design. Our family had a great time!"
Vacation Village in the Berkshires
10/10 Excellent
"No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose. "
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
10/10 Excellent
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
10/10 Excellent
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
Frequently asked questions
What accommodations do travelers like in Cheshire?
Can I book a refundable hotel in Cheshire?
If you're looking for the flexibility to change your travel plans to Cheshire, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Cheshire if I want a vacation home instead of a traditional hotel?
Browse 5 vacation homes on our site.
What will the weather in Cheshire be like during my vacation?
July and August are typically the warmest months in Cheshire when the average temp is 63°F. January and February are the coldest months when the average temperature is 25°F. July and August are the months with the most rain.
Why should I book my Cheshire hotel with Hotels.com?
There are lots of reasons to book your Cheshire trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.