Top 10 Hotels in Cheshire, MA from ￥9,974 - Competitive Prices

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 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

Gregory

￥40,085

￥42,370 total

includes taxes & fees

Oct 22 - Oct 23

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

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

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

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

2. The Springs Motel

New Ashford

Elizabeth

￥17,598

￥19,305 total

includes taxes & fees

Nov 4 - Nov 5

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

Denton

￥12,694

￥15,912 total

includes taxes & fees

Nov 2 - Nov 3

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

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

4. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Augusta

￥18,834

￥21,038 total

includes taxes & fees

Nov 2 - Nov 3

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

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

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

￥24,195

￥27,026 total

includes taxes & fees

Nov 8 - Nov 9

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

6. Hotel On North

Pittsfield

Lawrence

￥15,891

￥17,751 total

includes taxes & fees

Nov 2 - Nov 3

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

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

7. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

￥25,257

￥28,212 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

A rectangular swimming pool with a wooden deck surrounding it.

8. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

￥17,378

￥19,411 total

includes taxes & fees

Oct 14 - Oct 15

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

A hallway with a collection of plates on the walls, leading to a staircase.

9. The Porches Inn at Mass MoCA

North Adams

Ram

￥26,097

￥32,681 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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.

10. FairBridge Inn Express

Pittsfield

William

￥8,929

￥9,974 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

11. The Williams Inn

Williamstown

Soleil

￥27,177

￥30,356 total

includes taxes & fees

Nov 4 - Nov 5

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

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

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.

12. The Revival House

Adams

Katrina

￥23,548

￥26,304 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

13. The Yankee Inn

Lenox

William

￥16,748

￥18,708 total

includes taxes & fees

Nov 1 - Nov 2

A resort with multiple buildings, a parking area, and a mountainous backdrop.

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

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

14. Jiminy Peak Mountain Resort

Hancock

Jeffrey

￥21,188

￥23,667 total

includes taxes & fees

Oct 19 - Oct 20

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

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.

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

15. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

￥14,770

￥16,498 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

16. Willows Motel Williamstown

Williamstown

Charlene

￥13,359

￥14,922 total

includes taxes & fees

Nov 8 - Nov 9

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 hotel room with a desk, chair, TV, and a painting on the wall.

17. Rodeway Inn

Adams

Joann

￥10,610

￥11,851 total

includes taxes & fees

Nov 2 - Nov 3

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.

18. Maple Terrace Motel

Williamstown

Deborah

￥15,642

￥17,472 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

￥15,484

￥17,296 total

includes taxes & fees

Nov 6 - Nov 7

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

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

20. Berkshire Inn

Pittsfield

Kristina

￥12,771

￥14,265 total

includes taxes & fees

Nov 8 - Nov 9

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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

Top Cheshire Hotel Reviews

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

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

The Yankee Inn

10/10 Excellent

"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

Vacation Village in the Berkshires

10/10 Excellent

"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great stay, very clean, super comfortable beds. Will def stay again when in the area."

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

￥8,929

￥9,974 total

Nov 1 - Nov 2

includes taxes & fees

5.4/10 (918 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,482

￥13,943 total

Oct 20 - Oct 21

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥14,639

￥16,353 total

Nov 8 - Nov 9

includes taxes & fees

8.6/10 Excellent! (1,008 reviews)

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

1055 South Street Pittsfield MA

￥16,293

￥18,199 total

Nov 5 - Nov 6

includes taxes & fees

9.2/10 Wonderful! (230 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,748

￥18,708 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

￥20,548

￥22,952 total

Nov 2 - Nov 3

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 traveler data. Other good options for your stay in 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 vacation rentals in Cheshire?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation 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 hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

Where can I learn more about changing or cancelling my trip to Cheshire?

To find more details about updating your trip to Cheshire or cancelling it, click here.

What is the favorite LGBTQ-friendly accommodation 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 with an onsite pool. View all hotels with pools in Cheshire.

What is the best hotel near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations to choose from. Find out more about Cheshire.

What are the top places to visit 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. Check out what more to see and do in Expedia's Cheshire guide.

What's the seasonal weather like in Cheshire?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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Find hotels in Cheshire, MA from ￥9,974

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cheshire

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Cheshire hotels

1. Harbour House Inn

2. The Springs Motel

3. Vacation Village in the Berkshires

4. Hotel Downstreet, an Ascend Collection Hotel

5. Fairfield Inn & Suites by Marriott Williamstown

6. Hotel On North

7. The Trail in Adams - Berkshires’ Art Hotel

8. Howard Johnson by Wyndham Williamstown

9. The Porches Inn at Mass MoCA

10. FairBridge Inn Express

11. The Williams Inn

12. The Revival House

13. The Yankee Inn

14. Jiminy Peak Mountain Resort

15. Best Western Plus Berkshire Hills Inn & Suites

16. Willows Motel Williamstown

17. Rodeway Inn

18. Maple Terrace Motel

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

20. Berkshire Inn

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

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

Quality Inn Lee - Lenox South

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

Vacation Village in the Berkshires

Hotel Downstreet, an Ascend Collection Hotel

The Red Lion Inn

More cheap stays in Cheshire

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

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

The Yankee Inn

The Whitlock

Frequently asked questions

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