Cheshire Hotels

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Check prices for these dates

Tonight
Apr 5 - Apr 6
Tomorrow
Apr 6 - Apr 7
Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 19

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Our top choices for Cheshire hotels

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is P15,281
P16,152 total
includes taxes & fees
Apr 6 - Apr 7
Harbour House Inn
In-room safe, individually decorated, individually furnished, desk

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, (1,001 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is P7,408
P8,275 total
includes taxes & fees
Apr 8 - Apr 9
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is P5,581
P6,234 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Lee - Lenox South
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is P6,566
P7,202 total
includes taxes & fees
Apr 6 - Apr 7
Shaker Mill Inn
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is P13,553
P14,325 total
includes taxes & fees
Apr 6 - Apr 7
UU Rowe Camp and Conference Center
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (843 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is P4,758
P5,315 total
includes taxes & fees
Apr 6 - Apr 7
Howard Johnson by Wyndham Lenox
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
The price is P6,264
P6,997 total
includes taxes & fees
Apr 13 - Apr 14
Maple Terrace Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (888 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is P5,551
P6,201 total
includes taxes & fees
Apr 7 - Apr 8
Berkshires Untold
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean and cozy room, friendly staff, and fresh fruit for breakfast. Great location right next to Williams College."
United States
Phebe
The price is P4,864
P5,433 total
includes taxes & fees
Apr 8 - Apr 9
Willows Motel Williamstown
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (896 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is P4,771
P5,622 total
includes taxes & fees
Apr 12 - Apr 13
Cozy Corner Motel
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is P8,613
P9,621 total
includes taxes & fees
Apr 13 - Apr 14
Element Lenox Berkshires
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (783 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is P4,758
P5,315 total
includes taxes & fees
Apr 8 - Apr 9
The Villager Motel
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (297 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is P8,975
P10,526 total
includes taxes & fees
Apr 17 - Apr 18
Lakehouse Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is P5,638
P9,249 total
includes taxes & fees
Apr 6 - Apr 7
Blooming Inn
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (27 reviews)
"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 P9,040
P10,097 total
includes taxes & fees
Apr 6 - Apr 7
The Revival House
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (907 reviews)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is P5,420
P6,055 total
includes taxes & fees
Apr 6 - Apr 7
Howard Johnson by Wyndham Williamstown
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is P6,043
P6,750 total
includes taxes & fees
Apr 13 - Apr 14
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (673 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P8,534
P9,533 total
includes taxes & fees
Apr 9 - Apr 10
Hilton Garden Inn Lenox Pittsfield
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,001 reviews)
"Bathroom could use remodeling but otherwise a nice hotel. Staff are very friendly and helpful."
United States
Kara
The price is P8,441
P9,429 total
includes taxes & fees
May 3 - May 4
Hotel Downstreet, an Ascend Collection Hotel
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (208 reviews)
"Great stay! "
United States
ALEKSey
The price is P10,950
P11,574 total
includes taxes & fees
Apr 6 - Apr 7
Blue Vista Motor Lodge
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

This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very clean and updated. Park right outside your room. Nice bar with outdoor fireplace. Staff was amazing. Simple put, great place to stay!"
Joseph 1-night trip
Posted 4 hours ago
Berkshires Untold

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is P4,758 per night from Apr 6 to Apr 7
P4,758
P5,315 total
Apr 6 - Apr 7
includes taxes & fees

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 Berkshire Mountain Lodge. 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: Features a children's pool, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge 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 6 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 Susan B. Anthony Birthplace Museum 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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