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Top hotels and accommodation in Cheshire

Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
The price is NZ$236
includes taxes & fees
27 July - 28 July
Best Western Plus Berkshire Hills Inn & Suites
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (721)
"Great quiet stay. "
The price is NZ$183
includes taxes & fees
7 Aug - 8 Aug
The Villager Motel
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (835)
"Very, very clean with friendly owners. Located within a few minutes' drive of good restaurants and outdoor recreation areas. We would definitely stay again!"
The price is NZ$184
includes taxes & fees
24 Aug - 25 Aug
Cozy Corner Motel
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is NZ$413
includes taxes & fees
5 Aug - 6 Aug
Harbour House Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (765)
"Was great loved the jacuzzi tub "
The price is NZ$183
includes taxes & fees
27 July - 28 July
Howard Johnson by Wyndham Lenox
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (612)
"Convenient location for my trip"
The price is NZ$127
includes taxes & fees
27 July - 28 July
Wagon Wheel Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Good lodgings in a great area to visit."
The price is NZ$300
includes taxes & fees
30 July - 31 July
Hampton Inn & Suites Berkshires-Lenox
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (105)
"Great Place to stay in Small town"
The price is NZ$227
includes taxes & fees
18 Aug - 19 Aug
Blooming Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Loved the Yankee Inn!"
The price is NZ$236
includes taxes & fees
27 July - 28 July
The Yankee, Trademark Collection by Wyndham
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (785)
"It was a good place to sleep for a quick visit to Pittsfield. Glad we booked there. "
The price is NZ$160
includes taxes & fees
30 July - 31 July
Berkshire Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"The complimentary breakfast was amazing!"
The price is NZ$250
includes taxes & fees
6 Aug - 7 Aug
Quality Inn
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (929)
"Clean, conscientious service, great breakast spread. "
The price is NZ$191
includes taxes & fees
7 Aug - 8 Aug
Willows Motel Williamstown
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (855)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is NZ$203
includes taxes & fees
3 Aug - 4 Aug
Howard Johnson by Wyndham Williamstown
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1006)
"Great place"
The price is NZ$314
includes taxes & fees
3 Aug - 4 Aug
Hotel Downstreet, Ascend Hotel Collection
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (525)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
The price is NZ$224
includes taxes & fees
6 Aug - 7 Aug
Berkshire Mountain Lodge
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (985)
"Clean and convenient. Great value."
The price is NZ$126
includes taxes & fees
5 Aug - 6 Aug
Pleasant Valley Motel West Stockbridge
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NZ$375
includes taxes & fees
24 Aug - 25 Aug
Courtyard by Marriott Lenox Berkshires
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (614)
"It was a clean, well-run, low cost option. "
The price is NZ$118
includes taxes & fees
6 Aug - 7 Aug
Econo Lodge Lee - Great Barrington
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (829)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is NZ$238
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is NZ$438
includes taxes & fees
18 Aug - 19 Aug
The Porches Inn at Mass MoCA
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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Learn more about Cheshire

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

See all hotels in Cheshire
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

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

10/10 Excellent
"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all. "
Cheryl 1-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 Hotel Downstreet, Ascend Hotel Collection. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best holiday rentals that Cheshire has to offer?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This holiday home rental outside of Cheshire offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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?

Modern Berkshires home + private pool: Provides TVs, an outdoor pool and air conditioning. Vacation Village in the Berkshires and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are two additional hotels that feature an on-site pool.

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 3 hotels and other accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. 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.