Hotels in Cheshire from P4,354 for 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 gazebo in a garden with a house in the background.

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

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

P15,926

P16,834 total

includes taxes & fees

Oct 22 - Oct 23

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.

2. The Springs Motel

New Ashford

Elizabeth

P6,990

P7,668 total

includes taxes & fees

Nov 4 - Nov 5

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.

3. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Augusta

P7,481

P8,357 total

includes taxes & fees

Nov 2 - Nov 3

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.

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

4. Vacation Village in the Berkshires

Williamstown

Denton

P5,043

P6,321 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

P9,611

P10,735 total

includes taxes & fees

Nov 8 - Nov 9

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

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

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

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

6. The Porches Inn at Mass MoCA

North Adams

Ram

P10,367

P12,982 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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.

7. The Williams Inn

Williamstown

Soleil

P11,250

P12,567 total

includes taxes & fees

Nov 8 - Nov 9

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

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

8. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

P10,757

P12,015 total

includes taxes & fees

Oct 26 - Oct 27

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

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

9. The Revival House

Adams

Katrina

P9,356

P10,451 total

includes taxes & fees

Oct 27 - Oct 28

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

10. Hotel On North

Pittsfield

Lawrence

P6,312

P7,051 total

includes taxes & fees

Nov 3 - Nov 4

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

A rectangular swimming pool with a wooden deck surrounding it.

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

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

11. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

P6,903

P7,711 total

includes taxes & fees

Oct 12 - Oct 13

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

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

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

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

12. Jiminy Peak Mountain Resort

Hancock

Jeffrey

P8,417

P9,401 total

includes taxes & fees

Oct 18 - Oct 19

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

A hay bale display with pumpkins and scarecrows.

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.

13. Willows Motel Williamstown

Williamstown

Charlene

P5,307

P5,927 total

includes taxes & fees

Nov 2 - Nov 3

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 TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

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

14. FairBridge Inn Express

Pittsfield

William

P3,898

P4,354 total

includes taxes & fees

Oct 11 - Oct 12

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

15. The Yankee Inn

Lenox

William

P6,653

P7,431 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

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

16. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

P5,867

P6,554 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

A swimming pool with lounge chairs and a fence.

17. Maple Terrace Motel

Williamstown

Deborah

P6,214

P6,940 total

includes taxes & fees

Nov 3 - Nov 4

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

18. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

P6,151

P6,870 total

includes taxes & fees

Nov 6 - Nov 7

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 reception desk with a computer, a monitor, and a sign about Choice Privileges.

19. Rodeway Inn

Adams

Joann

P4,215

P4,708 total

includes taxes & fees

Nov 2 - Nov 3

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.

20. Williamstown Motel

Williamstown

Ahmet

P5,027

P5,616 total

includes taxes & fees

Nov 2 - Nov 3

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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."

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

P3,898

P4,354 total

Oct 11 - Oct 12

includes taxes & fees

5.4/10 (918 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

P4,958

P5,538 total

Oct 18 - Oct 19

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

P5,815

P6,495 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

P6,466

P7,222 total

Nov 5 - Nov 6

includes taxes & fees

9.2/10 Wonderful! (230 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

P6,653

P7,431 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

P8,109

P9,058 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.

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.

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 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.

Cheshire Hotels

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. Hotel Downstreet, an Ascend Collection Hotel

4. Vacation Village in the Berkshires

5. Fairfield Inn & Suites by Marriott Williamstown

6. The Porches Inn at Mass MoCA

7. The Williams Inn

8. The Trail in Adams - Berkshires’ Art Hotel

9. The Revival House

10. Hotel On North

11. Howard Johnson by Wyndham Williamstown

12. Jiminy Peak Mountain Resort

13. Willows Motel Williamstown

14. FairBridge Inn Express

15. The Yankee Inn

16. Best Western Plus Berkshire Hills Inn & Suites

17. Maple Terrace Motel

18. Holiday Inn & Suites Pittsfield-Berkshires by IHG

19. Rodeway Inn

20. Williamstown Motel

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

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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