Hotels in Cheshire from P4,281 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 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.

A gazebo in a garden with a house in the background.

1. Harbour House Inn

Cheshire

Gregory

P15,657

P16,549 total

includes taxes & fees

Aug 24 - Aug 25

A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.

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

A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Myrna

P7,344

P8,203 total

includes taxes & fees

Sep 20 - Sep 21

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

Victoria

P9,180

P10,254 total

includes taxes & fees

Sep 1 - Sep 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 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

4. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

P7,034

P7,857 total

includes taxes & fees

Sep 1 - Sep 2

A greenhouse with a transparent roof, a seating area with cushions, and a potted plant.

A cozy library with wooden bookshelves, a reading area, and a fireplace.

A living room with a fireplace, sofa, armchair, and a TV.

A living room with a grey sectional sofa, a small round coffee table, a brown leather armchair, and a window with curtains.

5. Berkshire Valley Inn

Williamstown

P10,275

P11,477 total

includes taxes & fees

Sep 7 - Sep 8

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.

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

6. Vacation Village in the Berkshires

Williamstown

Nyra

P5,361

P6,665 total

includes taxes & fees

Aug 31 - Sep 1

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 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.

7. The Revival House

Adams

James

P10,220

P11,416 total

includes taxes & fees

Aug 24 - Aug 25

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 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".

8. The Springs Motel

New Ashford

Shakeila

P7,359

P8,073 total

includes taxes & fees

Aug 24 - Aug 25

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, 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.

A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

9. Rodeway Inn

Adams

Andrew

P4,443

P4,963 total

includes taxes & fees

Aug 30 - Aug 31

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 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.

10. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

P11,350

P12,678 total

includes taxes & fees

Sep 20 - Sep 21

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.

11. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

P12,497

P13,959 total

includes taxes & fees

Sep 14 - Sep 15

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

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

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.

12. FairBridge Inn Express

Pittsfield

ERICIA

P3,832

P4,281 total

includes taxes & fees

Aug 24 - Aug 25

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

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

13. Jiminy Peak Mountain Resort

Hancock

Sandy

P8,831

P9,864 total

includes taxes & fees

Aug 30 - Aug 31

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 swimming pool with lounge chairs and a fence.

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

14. Maple Terrace Motel

Williamstown

Annette

P7,714

P8,617 total

includes taxes & fees

Sep 8 - Sep 9

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

15. Blue Vista Motor Lodge

North Adams

Frederic

P15,202

P16,068 total

includes taxes & fees

Aug 24 - Aug 25

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 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

Karen

P9,751

P10,891 total

includes taxes & fees

Sep 14 - Sep 15

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

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

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.

17. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

P6,788

P7,582 total

includes taxes & fees

Aug 24 - Aug 25

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 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.

18. Willows Motel Williamstown

Williamstown

Richard

P6,390

P7,138 total

includes taxes & fees

Aug 24 - Aug 25

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

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.

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

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

Pittsfield

Ken

P7,838

P8,755 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 residential street with a paved road, a lamp post, and flowering trees.

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

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

20. Berkshire Inn

Pittsfield

Adriana

P5,554

P6,203 total

includes taxes & fees

Aug 24 - Aug 25

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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 lake views.

See all hotels in Cheshire

Top Cheshire Hotel Reviews

The Whitlock

8/10 Good

"This is a very quaint hotel in a fantastic location. It is easy to walk to everything in Lenox and even Tanglewood from the hotel. Just be aware it is an uphill walk back from Tanglewood. The room was very spacious and bed very comfortable. Would definitely stay here again. If looking for any opportunities to improve, only thing I can come up with is a small frig in the room. Great place!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Lovely setting. Comfortable and well equipped townhouse. We are not much for the pool or mini golf type “activities” but we like the location near biking, hiking, theater and dance venues. And the ability to have meals in instead of using restaurants every meal. Looks like a great place for family vacations."

Quality Inn Lee - Lenox South

8/10 Good

"This is a very reasonably priced option for the area. Beds are comfortable and very quiet for sleeping. The property is older and could use some updates but room and halls are clean. Walkable to restaurants and a short drive to Tanglewood. Did not have the free breakfast but nice to have coffee/tea 24/7. There is breakfast place just next door that was excellent. Solid four stars and would stay again."

The Yankee Inn

8/10 Good

"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."

Vacation Village in the Berkshires

8/10 Good

"Price - quality =awesome"

The Red Lion Inn

10/10 Excellent

"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."

The Williams Inn

10/10 Excellent

"Wonderful property and the Barn is an excellent restaurant. Great coffee and sparkling water was available 24/7. Totally enjoyed our stay"

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

Howard Johnson by Wyndham Lenox

8/10 Good

"Room was clean and comfortable. Always nice to have a frig and microwave."

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

P3,832

P4,281 total

Aug 24 - Aug 25

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

P4,875

P5,446 total

Aug 31 - Sep 1

includes taxes & fees

7.6/10 Good! (903 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

P6,767

P7,559 total

Sep 14 - Sep 15

includes taxes & fees

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

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

P7,034

P7,857 total

Sep 1 - Sep 2

includes taxes & fees

8.6/10 Excellent! (1,007 reviews)

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

1055 South Street Pittsfield MA

P7,838

P8,755 total

Aug 31 - Sep 1

includes taxes & fees

9.4/10 Exceptional! (170 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

P9,751

P10,891 total

Sep 14 - Sep 15

includes taxes & fees

9.2/10 Wonderful! (1,018 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.

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 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. Holiday Inn & Suites Pittsfield-Berkshires by IHG

3. Hotel Downstreet, an Ascend Collection Hotel

4. Best Western Plus Berkshire Hills Inn & Suites

5. Berkshire Valley Inn

6. Vacation Village in the Berkshires

7. The Revival House

8. The Springs Motel

9. Rodeway Inn

10. Fairfield Inn & Suites by Marriott Williamstown

11. The Trail in Adams - Berkshires’ Art Hotel

12. FairBridge Inn Express

13. Jiminy Peak Mountain Resort

14. Maple Terrace Motel

15. Blue Vista Motor Lodge

16. The Yankee Inn

17. Howard Johnson by Wyndham Williamstown

18. Willows Motel Williamstown

19. Holiday Inn Express & Suites Pittsfield-Lenox-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

The Whitlock

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Yankee Inn

Vacation Village in the Berkshires

The Red Lion Inn

The Williams Inn

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

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

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