𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Cheshire from RM283 (2026) - Fully Refundable Options

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire hotels

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

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.

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

1. Harbour House Inn

Cheshire

Gregory

RM1,035

RM1,094 total

includes taxes & fees

30 Sept - 1 Oct

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

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

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

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

2. The Springs Motel

New Ashford

Elizabeth

RM468

RM514 total

includes taxes & fees

23 Sept - 24 Sept

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.

3. Vacation Village in the Berkshires

Williamstown

Jacob

RM388

RM478 total

includes taxes & fees

27 Sept - 28 Sept

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.

4. The Revival House

Adams

Katrina

RM622

RM695 total

includes taxes & fees

19 Oct - 20 Oct

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

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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.

5. The Yankee Inn

Lenox

William

RM478

RM533 total

includes taxes & fees

28 Sept - 29 Sept

An outdoor seating area with Adirondack chairs and potted plants.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

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

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

6. Cozy Corner Motel

Williamstown

Jonathan

RM360

RM423 total

includes taxes & fees

23 Sept - 24 Sept

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

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

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

A modern interior with a large window, a wooden table, and bar stools.

7. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Alexandra

RM585

RM653 total

includes taxes & fees

14 Oct - 15 Oct

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

A white two-story building with a porch, labeled as a motel.

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.

8. Willows Motel Williamstown

Williamstown

Bill

RM422

RM472 total

includes taxes & fees

4 Oct - 5 Oct

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

A hallway with a wooden door, a bench, and a staircase.

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

9. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

RM739

RM826 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

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

10. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

RM431

RM482 total

includes taxes & fees

18 Oct - 19 Oct

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

A swimming pool with lounge chairs and a fence.

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

A garden with a wooden pergola, potted plants, and a lawn with chairs.

11. Maple Terrace Motel

Williamstown

Jonathan

RM510

RM570 total

includes taxes & fees

24 Sept - 25 Sept

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

A dining area with wooden tables and chairs, a television, and a door with a sign.

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.

12. FairBridge Inn Express

Pittsfield

Horace

RM253

RM283 total

includes taxes & fees

20 Oct - 21 Oct

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

A rectangular swimming pool with a wooden deck surrounding it.

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

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

13. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

RM408

RM456 total

includes taxes & fees

23 Sept - 24 Sept

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

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

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

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

14. Hotel On North

Pittsfield

Drew

RM576

RM643 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

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.

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

RM444

RM496 total

includes taxes & fees

20 Oct - 21 Oct

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 kitchen with a fireplace, dining area, and a large window with curtains.

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

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

16. Williamstown Motel

Williamstown

Ahmet

RM441

RM492 total

includes taxes & fees

24 Sept - 25 Sept

A fire feature with a metal frame and a brick wall in the background.

A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

A reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

17. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

RM733

RM818 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A residential street with a paved road, a lamp post, and flowering trees.

18. Berkshire Inn

Pittsfield

Kristina

RM351

RM392 total

includes taxes & fees

20 Oct - 21 Oct

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A bar area with wooden beams, red chairs, and a long wooden table.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

19. The Williams Inn

Williamstown

William

RM792

RM885 total

includes taxes & fees

21 Oct - 22 Oct

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A spacious living room with a large sofa, a coffee table, and a fireplace.

20. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

RM597

RM667 total

includes taxes & fees

27 Sept - 28 Sept

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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

10.0/10 (1 review)

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 natural setting.

See all hotels in Cheshire

A lake surrounded by autumn-colored trees with a clear sky.

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Our third time there and the kids love it.. is quiet, love the pool and the kids love grilling food and sitting by the fire pit after."

Berkshires Untold

8/10 Good

"Liked he cleanliness. Room was very cold and no heat was available."

The Yankee Inn

10/10 Excellent

"The room was spacious, clean and comfortable. I will definitely stay there again."

The Williams Inn

10/10 Excellent

"Everything was great!"

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

10/10 Excellent

"The room was clean and perfect when we arrived! The pool area was a big hit with my boys and the breakfast the next morning was amazing!"

Jiminy Peak Mountain Resort

10/10 Excellent

"Even in the off season it was beautiful."

The Red Lion Inn

10/10 Excellent

"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Good"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

RM253

RM283 total

20 Oct - 21 Oct

includes taxes & fees

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

RM431

RM482 total

18 Oct - 19 Oct

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

RM447

RM499 total

19 Oct - 20 Oct

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

RM478

RM533 total

28 Sept - 29 Sept

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

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

1055 South Street Pittsfield MA

RM481

RM537 total

20 Oct - 21 Oct

includes taxes & fees

9.4/10 Exceptional! (216 reviews)

The Whitlock

16 Church St Lenox MA

RM565

RM631 total

23 Sept - 24 Sept

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 traveller data. Two other choices for your trip to the area are Berkshire Mountain Lodge and The Yankee Inn. 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 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?

Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and The Yankee Inn are two additional hotels that feature an on-site 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 accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

The picturesque setting of Mount Greylock State Reservation and Cheshire Reservoir exemplify the area's natural beauty. 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.

Cheshire hotels from RM283

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cheshire

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cheshire hotels

1. Harbour House Inn

2. The Springs Motel

3. Vacation Village in the Berkshires

4. The Revival House

5. The Yankee Inn

6. Cozy Corner Motel

7. Hotel Downstreet, an Ascend Collection Hotel

8. Willows Motel Williamstown

9. The Trail in Adams - Berkshires’ Art Hotel

10. Best Western Plus Berkshire Hills Inn & Suites

11. Maple Terrace Motel

12. FairBridge Inn Express

13. Howard Johnson by Wyndham Williamstown

14. Hotel On North

15. Holiday Inn & Suites Pittsfield-Berkshires by IHG

16. Williamstown Motel

17. Fairfield Inn & Suites by Marriott Williamstown

18. Berkshire Inn

19. The Williams Inn

20. Hilton Garden Inn Lenox Pittsfield

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Berkshires Untold

The Yankee Inn

The Williams Inn

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

Jiminy Peak Mountain Resort

The Red Lion Inn

Howard Johnson by Wyndham Lenox

More cheap stays in Cheshire

FairBridge Inn Express

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Lee - Lenox South

The Yankee Inn

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

The Whitlock

Frequently asked questions

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