Cheshire Holiday Rentals, Massachusetts: Private House Rentals

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

Apartment

Pool

Hot tub

Condo

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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 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.

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

฿8,516

฿9,001 total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

2. The Springs Motel

New Ashford

Elizabeth

฿3,557

฿3,902 total

includes taxes & fees

1 Nov - 2 Nov

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

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

3. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

฿4,001

฿4,469 total

includes taxes & fees

4 Nov - 5 Nov

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.

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

4. Vacation Village in the Berkshires

Williamstown

Pofen

฿2,697

฿3,381 total

includes taxes & fees

1 Nov - 2 Nov

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

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

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

฿4,697

฿5,246 total

includes taxes & fees

8 Nov - 9 Nov

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

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

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.

6. The Williams Inn

Williamstown

Soleil

฿6,819

฿7,617 total

includes taxes & fees

8 Nov - 9 Nov

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

7. The Revival House

Adams

Katrina

฿5,038

฿5,627 total

includes taxes & fees

2 Nov - 3 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.

8. Hotel On North

Pittsfield

Lawrence

฿4,501

฿5,028 total

includes taxes & fees

1 Nov - 2 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 motel with multiple rooms, a parking area, and a large tree in the foreground.

A rectangular swimming pool with a wooden deck surrounding it.

9. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

฿3,356

฿3,749 total

includes taxes & fees

22 Oct - 23 Oct

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."

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.

10. The Porches Inn at Mass MoCA

North Adams

Ram

฿5,266

฿6,632 total

includes taxes & fees

12 Nov - 13 Nov

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

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

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.

11. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

฿5,832

฿6,515 total

includes taxes & fees

2 Nov - 3 Nov

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

Olga

฿4,501

฿5,028 total

includes taxes & fees

19 Oct - 20 Oct

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 hay bale display with pumpkins and scarecrows.

13. Willows Motel Williamstown

Williamstown

David

฿2,838

฿3,170 total

includes taxes & fees

1 Nov - 2 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 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

14. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,138

฿3,505 total

includes taxes & fees

1 Nov - 2 Nov

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.

15. The Yankee Inn

Lenox

Basil

฿3,558

฿3,974 total

includes taxes & fees

1 Nov - 2 Nov

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 desk, computer, TV, and a chair.

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

16. FairBridge Inn Express

Pittsfield

William

฿2,085

฿2,328 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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

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

17. Maple Terrace Motel

Williamstown

Deborah

฿3,323

฿3,712 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A single-story building with a porch, a chimney, and a satellite dish.

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

18. Rodeway Inn

Adams

Joann

฿2,254

฿2,518 total

includes taxes & fees

12 Nov - 13 Nov

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

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

฿3,681

฿4,111 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

20. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

฿3,457

฿3,862 total

includes taxes & fees

13 Nov - 14 Nov

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 natural setting.

See all hotels in Cheshire

Top Cheshire Hotel Reviews

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Highly recommended, comfortable bed and beautiful cozy hotel"

The Yankee Inn

10/10 Excellent

"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"

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

10/10 Excellent

"Very clean and nice options for breakfast. Helpful staff."

Berkshires Untold

8/10 Good

"Enjoyed the view and the aesthetic"

Vacation Village in the Berkshires

10/10 Excellent

"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"

Hotel On North

10/10 Excellent

"Lovely clean spacious hotel with friendly staff!"

The Red Lion Inn

8/10 Good

"I enjoyed my stay, lovely little town. The Inn is beginning to show some signs of wear. A broken tile (baseboard) by the tub. However, staff pleasant and helpful. Excellent restaurants."

Berkshire Mountain Lodge

10/10 Excellent

"Great to have a whole suite not just a room. Even though a little outdated still very nice. Downsides were an absence of food vending machines for when you need a quick snack and don’t want to leave, and hot tub was under renovations which we weren’t made aware of until online check in. Overall very happy."

Quality Inn Lee - Lenox South

8/10 Good

"Short stay for business, but good value and a well-kept facility. No issues, Will stay there again."

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,085

฿2,328 total

15 Oct - 16 Oct

includes taxes & fees

5.4/10 (923 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,652

฿2,962 total

20 Oct - 21 Oct

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

฿3,110

฿3,474 total

3 Nov - 4 Nov

includes taxes & fees

8.6/10 Excellent! (1,005 reviews)

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

1055 South Street Pittsfield MA

฿3,323

฿3,712 total

11 Nov - 12 Nov

includes taxes & fees

9.2/10 Wonderful! (237 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,558

฿3,974 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

฿4,733

฿5,287 total

2 Nov - 3 Nov

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 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Cheshire on Expedia.com

Find hotels in Cheshire, MA from ฿2,328

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 Williams Inn

7. The Revival House

8. Hotel On North

9. Howard Johnson by Wyndham Williamstown

10. The Porches Inn at Mass MoCA

11. The Trail in Adams - Berkshires’ Art Hotel

12. Jiminy Peak Mountain Resort

13. Willows Motel Williamstown

14. Best Western Plus Berkshire Hills Inn & Suites

15. The Yankee Inn

16. FairBridge Inn Express

17. Maple Terrace Motel

18. Rodeway Inn

19. Hampton Inn & Suites Berkshires-Lenox

20. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

Courtyard by Marriott Lenox Berkshires

The Yankee Inn

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

Berkshires Untold

Vacation Village in the Berkshires

Hotel On North

The Red Lion Inn

Berkshire Mountain Lodge

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

Explore a world of travel with Expedia

Go further with the Expedia app