𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Cheshire (2026)

A lake surrounded by autumn-colored trees and hills.

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Pet friendly

Pool

Hot tub

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Family friendly

Waterpark

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

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

1. Harbour House Inn

Cheshire

Gregory

S$343

includes taxes & fees

9 Nov - 10 Nov

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

2. The Springs Motel

New Ashford

Elizabeth

S$156

includes taxes & fees

4 Nov - 5 Nov

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.

3. FairBridge Inn Express

Pittsfield

William

S$76

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

4. Rodeway Inn

Adams

Joann

S$96

includes taxes & fees

10 Nov - 11 Nov

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

5. Williamstown Motel

Williamstown

Ahmet

S$102

includes taxes & fees

8 Nov - 9 Nov

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.

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

6. Vacation Village in the Berkshires

Williamstown

Denton

S$129

includes taxes & fees

9 Nov - 10 Nov

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 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.

7. Willows Motel Williamstown

Williamstown

Charlene

S$121

includes taxes & fees

10 Nov - 11 Nov

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.

8. The Revival House

Adams

Katrina

S$213

includes taxes & fees

20 Oct - 21 Oct

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

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Julia

S$171

includes taxes & fees

5 Nov - 6 Nov

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

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

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

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

S$140

includes taxes & fees

6 Nov - 7 Nov

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

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

11. Cozy Corner Motel

Williamstown

Jonathan

S$113

includes taxes & fees

10 Nov - 11 Nov

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 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.

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

S$134

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A swimming pool with lounge chairs and a fence.

13. Maple Terrace Motel

Williamstown

Deborah

S$142

includes taxes & fees

10 Nov - 11 Nov

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

14. Berkshire Inn

Pittsfield

Kristina

S$116

includes taxes & fees

10 Nov - 11 Nov

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A compact living space with a kitchenette, a dining area, and a sofa.

A modern apartment with a living room, kitchenette, and dining area.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

15. The Central Downtown Inn & Suites

Pittsfield

Rena

S$142

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

16. Hotel On North

Pittsfield

Lawrence

S$192

includes taxes & fees

10 Nov - 11 Nov

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

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

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

A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

17. The Villager Motel

Williamstown

DONNA

S$113

includes taxes & fees

10 Nov - 11 Nov

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.

18. The Yankee Inn

Lenox

Basil

S$152

includes taxes & fees

1 Nov - 2 Nov

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

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

19. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

S$163

includes taxes & fees

7 Nov - 8 Nov

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

A rectangular swimming pool with a wooden deck surrounding it.

20. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

S$157

includes taxes & fees

12 Oct - 13 Oct

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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

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It was fine. No breakfast that I saw"

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

10/10 Excellent

"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."

Hotel On North

10/10 Excellent

"The hotel location is very good with convenient parking in the rear. We liked the large room. Lighting was a little dim in our room but it was very comfortable and spacious. The staff were very polite and helpful."

Vacation Village in the Berkshires

10/10 Excellent

"We were surprised by the space that we got!! The lay out of the suite was so pleasant. We enjoyed the stay tremendously."

The Yankee Inn

10/10 Excellent

"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."

Jiminy Peak Mountain Resort

8/10 Good

"The pool and hot tub were not heated enough. We didn't plan to use any other amenities so that was a disappointment. We enjoyed our stay. The room was good as we are our breakfast and dinner in the room. The kitchen was great and equipped with everything we needed."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Property was clean, staff was knowledgeable and cordial. Parking was very easy."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"no comment"

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!"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

S$76

10 Nov - 11 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

S$113

9 Nov - 10 Nov

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

S$133

10 Nov - 11 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

S$142

10 Nov - 11 Nov

includes taxes & fees

9.2/10 Wonderful! (232 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

S$152

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

The Whitlock

16 Church St Lenox MA

S$209

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (395 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.

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.

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Blandford Holiday Rentals

Cheshire Hotels from S$76

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. FairBridge Inn Express

4. Rodeway Inn

5. Williamstown Motel

6. Vacation Village in the Berkshires

7. Willows Motel Williamstown

8. The Revival House

9. Hotel Downstreet, an Ascend Collection Hotel

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

11. Cozy Corner Motel

12. Best Western Plus Berkshire Hills Inn & Suites

13. Maple Terrace Motel

14. Berkshire Inn

15. The Central Downtown Inn & Suites

16. Hotel On North

17. The Villager Motel

18. The Yankee Inn

19. Hampton Inn & Suites Berkshires-Lenox

20. Howard Johnson by Wyndham Williamstown

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

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

Hotel On North

Vacation Village in the Berkshires

The Yankee Inn

Jiminy Peak Mountain Resort

Hotel Downstreet, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

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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