Hotels in Cheshire

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Where to stay in Cheshire?

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

A gazebo in a lush garden with flowering plants and a large tree.

A spacious living room with a large window, a sofa, a chair, and a dining area.

A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.

1. Harbour House Inn

Cheshire

$254

$268 total

includes taxes & fees

Sep 17 - Sep 18

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

2. The Yankee Inn

Lenox

$116

$130 total

includes taxes & fees

Sep 22 - Sep 23

A patio area with outdoor furniture, a fire pit, and potted plants.

A cozy living room with a stone fireplace, comfortable seating, and a television.

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

3. The Springs Motel

New Ashford

$114

$125 total

includes taxes & fees

Sep 15 - Sep 16

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

A room with a hanging bed, a white wall, a window, and a door.

A garden with a wooden house, a tree, and a person tending to plants.

4. The Trail in Adams - Berkshires’ Art Hotel

Adams

$175

$195 total

includes taxes & fees

Sep 15 - Sep 16

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A spacious living room with large windows, a fireplace, and a variety of seating options.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

5. Vacation Village in the Berkshires

Williamstown

$112

$136 total

includes taxes & fees

Sep 15 - Sep 16

A living room with a fireplace, two sofas, and four black side tables.

A doorway leading to a room with a fireplace, a sofa, and decorative wall sconces.

A dining area with a wooden table, four chairs, and a framed picture on the wall.

A two-story building with a symmetrical facade, large columns, and a central entrance.

6. The Revival House

Adams

$166

$185 total

includes taxes & fees

Sep 15 - Sep 16

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

A single-story building with a porch, a chimney, and a satellite dish.

A reception desk with a computer, a monitor, and a sign about Choice Privileges.

7. Rodeway Inn

Adams

$72

$81 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

A modern hotel building with the name "Hotel Downtown" on the facade.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

8. Hotel Downstreet, an Ascend Collection Hotel

North Adams

$144

$160 total

includes taxes & fees

Sep 20 - Sep 21

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

9. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$110

$123 total

includes taxes & fees

Sep 16 - Sep 17

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

10. Williamstown Motel

Williamstown

$99

$111 total

includes taxes & fees

Sep 17 - Sep 18

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

A hotel room with a desk, computer, TV, and a chair.

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

11. FairBridge Inn Express

Pittsfield

$62

$69 total

includes taxes & fees

Sep 15 - Sep 16

An outdoor seating area with Adirondack chairs and potted plants.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

12. Cozy Corner Motel

Williamstown

$88

$104 total

includes taxes & fees

Sep 16 - Sep 17

A garden with a swing set, a blue chair, and a flower bed.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A swimming pool with lounge chairs and a fence.

13. Maple Terrace Motel

Williamstown

$125

$140 total

includes taxes & fees

Sep 15 - Sep 16

A buffet area with a counter, food items, and a beverage station.

A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

14. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

$115

$128 total

includes taxes & fees

Oct 12 - Oct 13

A building entrance with a large planter with purple flowers and a small tree.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A library with bookshelves, a television, and two armchairs.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

15. Hotel On North

Pittsfield

$152

$170 total

includes taxes & fees

Sep 15 - Sep 16

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

A hay bale display with pumpkins and scarecrows.

16. Willows Motel Williamstown

Williamstown

$109

$122 total

includes taxes & fees

Sep 15 - Sep 16

A building with a covered parking area and a grassy front yard.

A motel with multiple rooms, a parking area, and a large tree in the foreground.

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

17. Howard Johnson by Wyndham Williamstown

Williamstown

$110

$123 total

includes taxes & fees

Sep 15 - Sep 16

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

18. Berkshire Mountain Lodge

Pittsfield

$91

$124 total

includes taxes & fees

Oct 1 - Oct 2

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A motel with a parking lot, a swimming pool, and outdoor seating.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

19. Berkshire Inn

Pittsfield

$86

$96 total

includes taxes & fees

Sep 27 - Sep 28

A kitchen with a countertop, a refrigerator, and a window.

A park with picnic tables, a playground, and a large coniferous tree.

A kitchen with a refrigerator, a coffee maker, and a microwave.

A hotel room with two beds, a nightstand with a lamp, a television, and framed artwork on the wall.

20. The Villager Motel

Williamstown

$89

$99 total

includes taxes & fees

Sep 15 - Sep 16

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Go beyond your typical stay in Cheshire

Pet friendly

Hot tub

Pool

Cottage

Family friendly

Top landmarks in Cheshire

St Mary's of the Assumption Church

10.0/10 (1 review)

St Mary's of the Assumption Church is in the heart of Cheshire, so why not stop by during your stay.

See properties

Learn more about Cheshire

Cheshire is well-known for its attractions such as Mount Greylock State Reservation and Cheshire Reservoir.

See all hotels in Cheshire

A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.

Check out reviews of Cheshire hotels guests love

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The hotel is a perfect place to stay when attending a concert at Tanglewood. Its location is very convenient and our room was clean and comfortable. The on site restaurant (Mint) is lively and serves delicious Indian food."

Vacation Village in the Berkshires

10/10 Excellent

"Very large room and really easy check in. (Great Staff). Excellent value for the price."

The Yankee Inn

10/10 Excellent

"Loved the pond trail! What a nice shift after a long day on the road."

Berkshires Untold

8/10 Good

"Location was great! We loved the new addition in the front, where the reception area was, as well as restaurant and bar area, and library. Also liked the fire pits and outdoor seating. Rooms themselves were very basic and motel-like, and rather dark, but they did have nice bath products (shampoo, conditioner and body lotion). We didn’t realize there was also a room darkening shade on the front window, so the first night we just closed the curtain, which was see-thru! Staff was pleasant, and coffee was ready bright and early."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"All the staff I encountered were helpful and friendly. Room was modern and spacious. The free breakfast was very good. I loved the pool and the hot tub! I had an excellent 2-night stay!"

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Clean room, great location. Perfect base for a weekend in the Berkshires."

Quality Inn Lee - Lenox South

8/10 Good

"Therooms were loud on the lower level."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

Frequently asked questions

What accommodations do travelers like in Cheshire?

Guests like Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel and FairBridge Inn Express.

Can I book a refundable hotel in Cheshire?

If you're looking for the flexibility to change your travel plans to Cheshire, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Cheshire if I want a vacation home instead of a traditional hotel?

Browse 5 vacation homes on our site.

What will the weather in Cheshire be like during my vacation?

July and August are typically the warmest months in Cheshire when the average temp is 63°F. January and February are the coldest months when the average temperature is 25°F. July and August are the months with the most rain.

Why should I book my Cheshire hotel with Hotels.com?

There are lots of reasons to book your Cheshire trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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