Photo by Ed Gaffny

3 Stars Hotels in Cheshire, Massachusetts from CA $106

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Cheshire 3 Star Hotels

Top Cheshire 3 Star Hotels

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1944)
"It was a beautiful property with lots to do"
The price is CA $149
CA $182 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (557)
"Amazing place to stay. Can’t wait to go again. "
The price is CA $106
CA $149 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great location!"
The price is CA $209
CA $234 total
includes taxes & fees
Aug 17 - Aug 18
Hotel Downstreet, Ascend Hotel Collection

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (672)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is CA $221
CA $247 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (690)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."
The price is CA $126
CA $160 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is CA $264
CA $357 total
includes taxes & fees
Aug 18 - Aug 19
The Red Lion Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (856)
"Consistently a clean room with welcoming staff."
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (962)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is CA $219
CA $245 total
includes taxes & fees
Sep 1 - Sep 2
Jiminy Peak Mountain Resort

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Had a wonderful time "
The price is CA $174
CA $195 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (752)
"Staff were excellent and welcoming."
The price is CA $209
CA $234 total
includes taxes & fees
Sep 9 - Sep 10
Hotel On North

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is CA $176
CA $250 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (516)
"Great place , love it, will return"
The price is CA $209
CA $233 total
includes taxes & fees
Sep 10 - Sep 11
The Constance by the Lenox Collection

Gregory House Country Inn

3.0 star property
8.8 out of 10, Excellent, (54)
"Big rooms, very friendly staff and great pizza!"
The price is CA $155
CA $172 total
includes taxes & fees
Aug 17 - Aug 18
Gregory House Country Inn

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (569)
"Fabulous place"
The price is CA $209
CA $234 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (407)
"Very comfortable room that worked great for our family. "
The price is CA $259
CA $320 total
includes taxes & fees
Sep 2 - Sep 3
The Porches Inn at Mass MoCA

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (639)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is CA $207
CA $231 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lenox Pittsfield

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (109)
"Lovely Inn and very responsive and approachable staff. "
The price is CA $133
CA $217 total
includes taxes & fees
Aug 20 - Aug 21
Blooming Inn

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is CA $240
CA $268 total
includes taxes & fees
Sep 10 - Sep 11
The Dewey

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
The price is CA $225
CA $252 total
includes taxes & fees
Aug 14 - Aug 15
Whistler's Inn Bed & Breakfast

The Revival House

3.0 star property
9.4 out of 10, Exceptional, (10)
"Self check in was easy. Rooms were spacious and clean. Great place."
The price is CA $248
CA $277 total
includes taxes & fees
Aug 17 - Aug 18
The Revival House
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Cheshire.
Still don't see what you're looking for?
See all properties in Cheshire.
You can also use these popular filters to refine your search.
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.

Learn more about Cheshire

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

Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

Frequently asked questions

What are the best 3-star hotels in Cheshire?
Travellers in search of a comfortable and affordable Cheshire property often book Club Wyndham Bentley Brook. This 3-star hotel, roughly 10 kilometres west of the centre, comes with a swimming pool and a barbecue grill. Need another suggestion? Located 14 kilometres southwest of downtown and including mountain views and WiFi, Hotel On North is also a go-to choice for guests.
How much does it cost to stay in a 3-star hotel in Cheshire?
Discover the ideal trifecta of quality, comfort and affordability at a 3-star hotel in Cheshire with Expedia's filter tools. Key in your travel dates and then narrow down your search according to the rate you want to pay per night.

  • Search for the lowest price per night right now from CA $158

What is the difference between a 4-star and 3-star hotel in Cheshire?
Relaxation is easy in 3-star hotels in Cheshire. Alongside cozy surroundings, these more affordable properties include an array of welcome amenities like free WiFi, coffee and tea maker and a gym. A 4-star hotel offers a more sophisticated ambience with superior features such as a spa centre, swimming pool and more spacious rooms. Regardless of your preferred hotel style or how much you want to spend, Expedia has a perfect fit for you.