Photo by Ed Gaffny

Find 3 Star Hotels in Cheshire, MA from AED 319

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Check availability on Cheshire 3 Star Hotels

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Compare Cheshire 3 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Clean,friendly staff and great location."
The price is AED 528
AED 589 total
includes taxes & fees
1 Sep - 2 Sep
Hotel Downstreet, Ascend Hotel Collection

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1922)
"Great stay with all plenty of things to do…"
The price is AED 319
AED 397 total
includes taxes & fees
25 Aug - 26 Aug
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (843)
"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 AED 422
AED 472 total
includes taxes & fees
1 Sep - 2 Sep
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

3.5 star property
9.0 out of 10, Wonderful, (683)
"Had a great time"
The price is AED 438
AED 540 total
includes taxes & fees
2 Sep - 3 Sep
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (656)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is AED 1,558
AED 1,740 total
includes taxes & fees
8 Aug - 9 Aug
Berkshires Untold

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (749)
"Staff were excellent and welcoming."
The price is AED 694
AED 775 total
includes taxes & fees
3 Aug - 4 Aug
Hotel On North

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is AED 680
AED 924 total
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (507)
"Property was excellent "
The price is AED 590
AED 659 total
includes taxes & fees
2 Sep - 3 Sep
The Constance by the Lenox Collection

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (536)
"Excellent stay!"
The price is AED 348
AED 471 total
includes taxes & fees
24 Aug - 25 Aug
Berkshire Mountain Lodge

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is AED 465
AED 520 total
includes taxes & fees
1 Sep - 2 Sep
The Black Swan Lee - Lenox, Ascend Hotel Collection

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (957)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is AED 584
AED 652 total
includes taxes & fees
1 Sep - 2 Sep
Jiminy Peak Mountain Resort

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 AED 558
AED 624 total
includes taxes & fees
1 Sep - 2 Sep
Courtyard by Marriott Lenox Berkshires

Gregory House Country Inn

3.0 star property
9.0 out of 10, Wonderful, (48)
"Wonderful stay and the food is excellent"
The price is AED 413
AED 459 total
includes taxes & fees
5 Aug - 6 Aug
Gregory House Country Inn

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is AED 490
AED 690 total
includes taxes & fees
27 Aug - 28 Aug
The Cornell Inn, Lenox & The Berkshires

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (402)
"Very comfortable room that worked great for our family. "
The price is AED 684
AED 846 total
includes taxes & fees
2 Sep - 3 Sep
The Porches Inn at Mass MoCA

The Dewey

3.5 star property
8.8 out of 10, Excellent, (318)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is AED 665
AED 743 total
includes taxes & fees
2 Sep - 3 Sep
The Dewey

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is AED 583
AED 652 total
includes taxes & fees
2 Sep - 3 Sep
Hilton Garden Inn Lenox Pittsfield

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (8)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is AED 661
AED 738 total
includes taxes & fees
3 Aug - 4 Aug
The Revival House

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (107)
"Lovely Inn and very responsive and approachable staff. "
The price is AED 360
AED 545 total
includes taxes & fees
18 Aug - 19 Aug
Blooming Inn
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Cheshire.
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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 wildlife.

The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..
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?
Club Wyndham Bentley Brook, around 16 kilometers west of downtown Cheshire, is a guest favorite. A swimming pool and a sauna are just two of its amenities. Hotel On North is another 3-star hotel that gets great reviews from travelers. It offers premium bedding and mountain views, and is about 23 kilometers southwest of the center.
How much does it cost to stay in a 3-star hotel in Cheshire?
Use Expedia's sort and search filters to lock in a great-value 3-star hotel for your upcoming Cheshire trip. Just set your maximum rate with our convenient pricing tool. You can also pick the amenities you'd like, desired neighborhood and a lot more.

  • Search for the lowest price per night right now from AED 422

What is the difference between a 4-star and 3-star hotel in Cheshire?
The principal difference between a 3- and 4-star hotel in Cheshire is the level of service and access to creature comforts. Three-star hotels are generally more economical and come with the services and amenities you need for your comfort, such as a gym, breakfast and WiFi. You can count on a bit more at a 4-star hotel — think upscale décor, deluxe toiletries and extras like on-site spa centers.