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Cheshire hotels from HK$654

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24 Dec - 25 Dec
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Our top choices for Cheshire hotels

Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
Unwind at this cosy Cheshire inn offering free WiFi and parking. Explore nearby Mount Greylock State Reservation or catch a show at Adams Theatre, then return to comfortable accommodation just 16 minutes from Pittsfield Station.
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is HK$1,672
HK$1,767 total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is HK$951
HK$1,062 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
Frette Italian sheets, premium bedding, down duvets, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (448)
"It is the perfect place to stay!"
United States
Darrell
The price is HK$1,117
HK$1,422 total
includes taxes & fees
22 Jan - 23 Jan 2026
The Porches Inn at Mass MoCA
In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
This motel offers a peaceful retreat with 2 hot tubs and a rejuvenating sauna. Located near Florida Free Public Library, guests praise the helpful staff and clean rooms. Enjoy free WiFi and parking during your North Adams adventure.
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is HK$1,389
HK$1,468 total
includes taxes & fees
28 Dec - 29 Dec
Blue Vista Motor Lodge
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (460)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is HK$532
HK$596 total
includes taxes & fees
25 Dec - 26 Dec
Berkshire Travel Lodge
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

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, (143)
Immerse yourself in this artistic B&B offering hiking trails right from the property. Close to Adams Theatre and the Berkshire Scenic Railway Museum, this boutique hotel provides free WiFi, parking, and daily housekeeping.
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is HK$1,351
HK$1,509 total
includes taxes & fees
25 Dec - 26 Dec
The Trail in Adams - Berkshires’ Art Hotel
Desk, iron/ironing board, free WiFi
The Revival House

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
Unwind at this charming guesthouse offering free perks including WiFi, parking, and daily breakfast. Located near Adams Theatre and Berkshire Scenic Railway Museum, this cosy retreat provides a perfect base for exploring local attractions.
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is HK$1,167
HK$1,304 total
includes taxes & fees
29 Dec - 30 Dec
The Revival House
Front of property
Becket Motel

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60)
Nestled in the quaint town of Becket, this motel offers complimentary WiFi and parking just moments from the Historic Quarry. Explore nearby hiking trails before returning to comfortable rooms with convenient room service.
"Comfortable stay "
United States
Paul
The price is HK$694
HK$1,036 total
includes taxes & fees
27 Dec - 28 Dec
Becket Motel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (68)
Located 10 minutes from Tanglewood Music Centre, this hotel provides complimentary breakfast, WiFi, and parking. After exploring nearby attractions, unwind in the indoor pool or soothing hot tub for a peaceful end to your Pittsfield adventure.
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is HK$880
HK$982 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is HK$731
HK$817 total
includes taxes & fees
25 Dec - 26 Dec
The Central Downtown Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
Peaceful accommodation in a safe location make this motel a smart choice for travellers. Free perks include WiFi and self parking, while the 24-hour front desk ensures assistance anytime. Nearby attractions and skiing opportunities add adventure to your restful stay.
"Room spotless and staff helpful."
United States
William
The price is HK$623
HK$696 total
includes taxes & fees
7 Jan - 8 Jan 2026
FairBridge Inn Express
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
Relax in this Lenox retreat with seasonal outdoor pool and tennis courts. Located just 5 minutes from Tanglewood Music Centre, with nearby access to Ventfort Hall Mansion and The Bookshop. Enjoy refreshments at the bar/lounge after exploring the charming grounds.
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is HK$1,702
HK$1,902 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Terrace Inn
Front of property
Gregory House Country Inn

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (85)
Escape to this welcoming inn in Averill Park where free WiFi and parking await. The on-site restaurant serves delicious meals, while the bar offers relaxing drinks after exploring nearby attractions. Daily housekeeping ensures a comfortable stay.
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is HK$840
HK$933 total
includes taxes & fees
27 Dec - 28 Dec
Gregory House Country Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Centre. Close to Colonial Theatre and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is HK$615
HK$688 total
includes taxes & fees
5 Jan - 6 Jan 2026
Berkshire Inn
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1001)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness centre or enjoy nearby skiing options. Tanglewood Music Centre and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"Very friendly and good Breakfast."
United States
Jesse
The price is HK$594
HK$663 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (125)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is HK$504
HK$945 total
includes taxes & fees
5 Jan - 6 Jan 2026
Blooming Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness centre. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is HK$995
HK$1,111 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is HK$768
HK$1,031 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
This charming bed and breakfast in Lenox offers a complimentary full breakfast daily. Enjoy free WiFi and parking while staying minutes from Lenox Library and The Bookshop. Pittsfield Municipal Airport is just an 11-minute drive away.
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is HK$3,082
HK$3,443 total
includes taxes & fees
18 Jan - 19 Jan 2026
33 Main
Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
Relax in this Lenox retreat featuring poolside drinks and a garden oasis. Just minutes from Shakespeare and Company, this B&B offers free breakfast, WiFi and parking. Guests consistently praise the attentive staff for an exceptional stay.
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
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.
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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes.
See properties

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and local cuisine.

See all hotels in Cheshire
An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"A wonderful property with excellent amenities. The heated outdoor pool and sauna were clean and easily accessible. I travel with my small dog and my room was great. They actually upgraded me to a suite! I would stay here again without question. It is across the street from Mass MOCa, an extraordinary museum. Staff was courteous and helpful. "
Carleen 1-night trip
Posted 3 days ago
The Porches Inn at Mass MoCA

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
The price is HK$594 per night from 5 Jan to 6 Jan
HK$594
HK$663 total
5 Jan - 6 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Williams Inn and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best holiday rentals that Cheshire has to offer?
Peace and quiet on the lake: This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG and The Yankee, Trademark Collection by Wyndham are two additional hotels that feature an on-site pool. View all hotels with pools in Cheshire.
What is staying in Cheshire like?
Visitors can enjoy all that Cheshire has to offer, including the ski areas, restaurants and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 5 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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