Cheshire Hotels

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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 cozy Cheshire inn offering free WiFi and parking. Explore nearby Mount Greylock State Reservation or catch a show at Adams Theater, then return to comfortable accommodations just 16 minutes from Pittsfield Station.
"Nice place for a weekend away."
United States
Gregory
The price is P12,655
P13,377 total
includes taxes & fees
Jan 7 - Jan 8
Harbour House Inn
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
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, (1002)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is P6,827
P7,626 total
includes taxes & fees
Feb 2 - Feb 3
Hotel Downstreet, an Ascend Collection Hotel
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 P10,512
P11,111 total
includes taxes & fees
Jan 6 - Jan 7
Blue Vista Motor Lodge
Frette Italian sheets, premium bedding, down comforters, 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, (451)
"It is the perfect place to stay!"
United States
Darrell
The price is P8,456
P10,760 total
includes taxes & fees
Feb 3 - Feb 4
The Porches Inn at Mass MoCA
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (461)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is P3,973
P4,449 total
includes taxes & fees
Jan 6 - Jan 7
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, (144)
Immerse yourself in this artistic B&B offering hiking trails right from the property. Close to Adams Theater 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 P10,227
P11,424 total
includes taxes & fees
Jan 6 - Jan 7
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 Theater and Berkshire Scenic Railway Museum, this cozy 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 P8,834
P9,867 total
includes taxes & fees
Jan 12 - Jan 13
The Revival House
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, (72)
Located 10 minutes from Tanglewood Music Center, 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.
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is P7,214
P8,058 total
includes taxes & fees
Jan 8 - Jan 9
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, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is P5,533
P6,181 total
includes taxes & fees
Jan 6 - Jan 7
The Central Downtown Inn & Suites
Private kitchen
Two Brooks Lodge

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3)
Surrounded by nature in Bennington, this vacation home offers hiking and mountain biking paths right outside your door. Near the train station with free WiFi and parking, plus a terrace and memory foam bed for ultimate relaxation after exploring nearby museums.
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
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 accommodations in a safe location make this motel a smart choice for travelers. 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 P4,715
P5,266 total
includes taxes & fees
Jan 18 - Jan 19
FairBridge Inn Express
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, (1002)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness center or enjoy nearby skiing options. Tanglewood Music Center 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 P4,496
P5,022 total
includes taxes & fees
Jan 7 - Jan 8
Best Western Plus Berkshire Hills Inn & Suites
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, (841)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Center. Close to Colonial Theater 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 P5,062
P5,654 total
includes taxes & fees
Jan 19 - Jan 20
Berkshire 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, (660)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness center. 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.
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,527
P8,408 total
includes taxes & fees
Jan 9 - Jan 10
Hilton Garden Inn Lenox Pittsfield
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 Center, with nearby access to Ventfort Hall Mansion and The Bookstore. 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 P12,885
P14,392 total
includes taxes & fees
Jan 20 - Jan 21
Hampton Terrace Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
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.
"great stall and friendly pet friendly place"
United States
bonnie
The price is P5,809
P7,803 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge
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 P6,622
P7,350 total
includes taxes & fees
Jan 6 - Jan 7
Gregory House Country Inn
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is P25,016
P27,443 total
includes taxes & fees
Jan 20 - Jan 21
Inn at Kenmore Hall
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 Bookstore. 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 P23,560
P26,316 total
includes taxes & fees
Jan 18 - Jan 19
33 Main
Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very Good, (195)
Enjoy elegant accommodations at this boutique inn featuring a restaurant and bar/lounge in the heart of Lenox. Near Lenox Library and The Bookstore, with free WiFi and parking for easy exploration of Berkshires attractions.
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is P9,839
P11,483 total
includes taxes & fees
Jan 6 - Jan 7
Gateways Inn & Restaurant
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"The front desk lady was super nice and helpful. Checkin was quick and effortless :) My only complaints are we had a room near where they were doing construction, so that was kinda noisy. Also, when I reserved a room online I made sure I got one with the fridge and microwave. I didn't notcie4 until after we settled in and wanted to heat up leftovers that we didn't have a microwave :( :( At that point I was too tired from traveling to call down to the front desk."
TONYA 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

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 P4,496 per night from Jan 7 to Jan 8
P4,496
P5,022 total
Jan 7 - Jan 8
includes taxes & fees
8.4/10 Very Good! (1,002 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 traveler data. Other good options for your stay in the area are Hotel Downstreet, an Ascend Collection Hotel and The Williams Inn. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What is the favorite LGBTQ-friendly accommodation 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. Hotel Downstreet, an Ascend Collection Hotel and Holiday Inn & Suites Pittsfield-Berkshires by IHG are two additional hotels with an onsite 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 accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Adams Theater in the area. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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