Top 10 Hotels in Cheshire, MA from ₩95,470 - Competitive Prices

A lake surrounded by autumn-colored trees and hills.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Cheshire

Pet friendly

Pool

Apartment

Hot tub

Condo

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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 gazebo in a garden with a house in the background.

1. Harbour House Inn

Cheshire

Gregory

₩349,177

₩369,081 total

includes taxes & fees

Aug 31 - Sep 1

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

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

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

2. Vacation Village in the Berkshires

Williamstown

Alex

₩133,053

₩163,718 total

includes taxes & fees

Sep 1 - Sep 2

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

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.

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

3. Willows Motel Williamstown

Williamstown

Richard

₩116,370

₩129,982 total

includes taxes & fees

Sep 1 - Sep 2

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

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

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

A swimming pool with lounge chairs and a fence.

4. Maple Terrace Motel

Williamstown

Annette

₩172,043

₩192,179 total

includes taxes & fees

Sep 9 - Sep 10

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

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 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.

5. The Yankee Inn

Lenox

Karen

₩209,204

₩233,675 total

includes taxes & fees

Sep 27 - Sep 28

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

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

A spacious lobby with a fireplace, seating area, and a bar.

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

6. Berkshire Mountain Lodge

Pittsfield

Robert

₩130,196

₩176,176 total

includes taxes & fees

Aug 31 - Sep 1

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

A multi-story hotel with a brick facade and a flat roof.

A pool area with a glass ceiling, multiple levels, and outdoor seating.

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Nicole

₩162,408

₩181,415 total

includes taxes & fees

Sep 7 - Sep 8

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

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

8. Cozy Corner Motel

Williamstown

Janis

₩121,393

₩142,685 total

includes taxes & fees

Sep 9 - Sep 10

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

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

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Peter

₩209,204

₩233,681 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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

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

10. The Villager Motel

Williamstown

Rebecca

₩122,494

₩136,822 total

includes taxes & fees

Sep 1 - Sep 2

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 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.

11. Hotel On North

Pittsfield

Drew

₩246,365

₩275,190 total

includes taxes & fees

Sep 7 - Sep 8

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.

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

₩157,990

₩176,475 total

includes taxes & fees

Sep 20 - Sep 21

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

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

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

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

13. Howard Johnson by Wyndham Lenox

Lenox

Sheila

₩108,731

₩121,453 total

includes taxes & fees

Aug 31 - Sep 1

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

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.

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

14. The Springs Motel

New Ashford

Elizabeth

₩168,773

₩185,144 total

includes taxes & fees

Aug 31 - Sep 1

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

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

15. Berkshire Inn

Pittsfield

Adriana

₩118,351

₩132,198 total

includes taxes & fees

Aug 31 - Sep 1

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

16. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

₩170,878

₩190,872 total

includes taxes & fees

Sep 13 - Sep 14

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 modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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

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

Pittsfield

Ken

₩162,408

₩181,415 total

includes taxes & fees

Sep 8 - Sep 9

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 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

₩247,081

₩275,990 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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

19. FairBridge Inn Express

Pittsfield

ERICIA

₩85,470

₩95,470 total

includes taxes & fees

Sep 13 - Sep 14

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

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

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.

20. Jiminy Peak Mountain Resort

Hancock

Christopher

₩196,954

₩219,997 total

includes taxes & fees

Aug 31 - Sep 1

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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 lake views.

See all hotels in Cheshire

Top Cheshire Hotel Reviews

The Yankee Inn

8/10 Good

"Independent option convenient to Tanglewood. Spacious room and facility. Breakfast included but needs better coffee and some other tweaks."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

Vacation Village in the Berkshires

10/10 Excellent

"Friendly and professional staff. Check in quick and easy. Will definitely stay again"

Quality Inn Lee - Lenox South

8/10 Good

"Ok hotel"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Amazing time. Stayed in the Presidential units. Worth it."

Hotel On North

10/10 Excellent

"One of my favorite hotels in America - for real!"

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Room was"

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

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

₩85,470

₩95,470 total

Sep 13 - Sep 14

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

₩108,731

₩121,453 total

Aug 31 - Sep 1

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

₩150,916

₩168,573 total

Sep 20 - Sep 21

includes taxes & fees

8.4/10 Very Good! (1,004 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

₩157,990

₩176,475 total

Sep 20 - Sep 21

includes taxes & fees

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

1055 South Street Pittsfield MA

₩162,408

₩181,415 total

Sep 8 - Sep 9

includes taxes & fees

9.4/10 Exceptional! (176 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

₩209,204

₩233,675 total

Sep 27 - Sep 28

includes taxes & fees

9.2/10 Wonderful! (1,003 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 traveler data. Other good options for your stay in the area are The Yankee Inn and Berkshire Mountain Lodge. 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 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. The Yankee Inn and Berkshire Mountain Lodge 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Cheshire on Expedia.com

Find hotels in Cheshire, MA from ₩95,470

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. Vacation Village in the Berkshires

3. Willows Motel Williamstown

4. Maple Terrace Motel

5. The Yankee Inn

6. Berkshire Mountain Lodge

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

8. Cozy Corner Motel

9. Hotel Downstreet, an Ascend Collection Hotel

10. The Villager Motel

11. Hotel On North

12. Best Western Plus Berkshire Hills Inn & Suites

13. Howard Johnson by Wyndham Lenox

14. The Springs Motel

15. Berkshire Inn

16. Hampton Inn & Suites Berkshires-Lenox

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

18. Fairfield Inn & Suites by Marriott Williamstown

19. FairBridge Inn Express

20. Jiminy Peak Mountain Resort

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

The Yankee Inn

Berkshires Untold

Vacation Village in the Berkshires

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

The Cornell Inn, Lenox & The Berkshires

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

More cheap stays in Cheshire

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

Best Western Plus Berkshire Hills Inn & Suites

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

The Yankee Inn

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app