Best Cheshire Hotels in 2026 from HK$544 - 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 gazebo in a garden with a house in the background.

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.

1. Harbour House Inn

Cheshire

Gregory

HK$1,990

HK$2,103 total

includes taxes & fees

28 Sept - 29 Sept

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

2. The Springs Motel

New Ashford

Elizabeth

HK$873

HK$958 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

3. Vacation Village in the Berkshires

Williamstown

Jacob

HK$746

HK$920 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A bedroom with a bed, a sofa, a fireplace, and a chandelier.

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

4. The Revival House

Adams

Katrina

HK$1,299

HK$1,451 total

includes taxes & fees

27 Sept - 28 Sept

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 hay bale display with pumpkins and scarecrows.

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.

5. Willows Motel Williamstown

Williamstown

Linda

HK$812

HK$907 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Alexandra

HK$1,060

HK$1,184 total

includes taxes & fees

14 Oct - 15 Oct

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

A swimming pool with lounge chairs and a fence.

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

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

7. Maple Terrace Motel

Williamstown

Deborah

HK$1,012

HK$1,130 total

includes taxes & fees

28 Sept - 29 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 fitness center including a weight machine, an elliptical, and a treadmill.

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

8. FairBridge Inn Express

Pittsfield

Horace

HK$487

HK$544 total

includes taxes & fees

28 Sept - 29 Sept

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A snack bar with shelves of snacks and a refrigerated display.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Susan

HK$957

HK$1,069 total

includes taxes & fees

19 Oct - 20 Oct

An outdoor seating area with Adirondack chairs and potted plants.

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

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

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

10. Cozy Corner Motel

Williamstown

Jonathan

HK$692

HK$813 total

includes taxes & fees

28 Sept - 29 Sept

An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

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

A conference room with a whiteboard, tables, and chairs.

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

HK$839

HK$938 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

12. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

HK$620

HK$692 total

includes taxes & fees

27 Sept - 28 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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

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.

13. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

HK$830

HK$927 total

includes taxes & fees

19 Oct - 20 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 garden with a wooden house, a tree, and a person tending to plants.

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.

14. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

HK$1,421

HK$1,588 total

includes taxes & fees

28 Sept - 29 Sept

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

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.

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

Drew

HK$1,053

HK$1,176 total

includes taxes & fees

5 Oct - 6 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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

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

16. The Yankee Inn

Lenox

William

HK$847

HK$946 total

includes taxes & fees

27 Oct - 28 Oct

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

A spacious living area with a fireplace, wooden beams, and a large window.

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

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

17. The Williams Inn

Williamstown

William

HK$1,524

HK$1,702 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.

18. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

HK$1,408

HK$1,573 total

includes taxes & fees

1 Oct - 2 Oct

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

19. Berkshire Inn

Pittsfield

Kristina

HK$674

HK$753 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

20. Williamstown Motel

Williamstown

Ahmet

HK$863

HK$964 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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"It’s an older facility , as expected, but with great character and very clean . Special praise goes to the staff , in particular , Michele at the front desk . Super nice and very helpful in answering our questions about the local activities . Will keep in mind for another visit ."

Berkshires Untold

10/10 Excellent

"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

Quality Inn Lee - Lenox South

10/10 Excellent

"Very clean and comfortable. Some of the mechanicals are older but the rooms are quite fresh. Excellent location. Pretty good breakfast. Excellent value."

The Red Lion Inn

10/10 Excellent

"A most amazing place to stay! Has everything a hotel should have - we had a very large room! Great porch! We have stayed there several times."

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"Toilet was faulty but they gave us another room. Not much variety on the breakfast"

Berkshire Mountain Lodge

8/10 Good

"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

HK$487

HK$544 total

28 Sept - 29 Sept

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

HK$620

HK$692 total

27 Sept - 28 Sept

includes taxes & fees

7.6/10 Good! (917 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

HK$847

HK$946 total

27 Oct - 28 Oct

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

HK$860

HK$961 total

19 Oct - 20 Oct

includes taxes & fees

8.4/10 Very good! (1,006 reviews)

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

1055 South Street Pittsfield MA

HK$957

HK$1,069 total

19 Oct - 20 Oct

includes taxes & fees

The Whitlock

16 Church St Lenox MA

HK$1,087

HK$1,214 total

28 Sept - 29 Sept

includes taxes & fees

8.4/10 Very good! (387 reviews)

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.

What are some of the best holiday rentals that Cheshire has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Cheshire is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. See all 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 HK$544

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. Willows Motel Williamstown

6. Hotel Downstreet, an Ascend Collection Hotel

7. Maple Terrace Motel

8. FairBridge Inn Express

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

10. Cozy Corner Motel

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

12. Howard Johnson by Wyndham Lenox

13. Best Western Plus Berkshire Hills Inn & Suites

14. The Trail in Adams - Berkshires’ Art Hotel

15. Hotel On North

16. The Yankee Inn

17. The Williams Inn

18. Fairfield Inn & Suites by Marriott Williamstown

19. Berkshire Inn

20. Williamstown Motel

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Red Lion Inn

The Whitlock

Hampton Inn & Suites Berkshires-Lenox

Berkshire Mountain Lodge

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Cheshire

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

The Yankee Inn

Quality Inn Lee - Lenox South

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

The Whitlock

Frequently asked questions

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