Cheshire Holiday Rentals, Massachusetts: Private House Rentals

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

฿8,566

฿9,054 total

includes taxes & fees

28 Oct - 29 Oct

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

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".

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

2. The Springs Motel

New Ashford

Elizabeth

฿3,571

฿3,917 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

A room with large windows, a red patterned rug, a wooden table with benches, and shelves with figurines.

3. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

฿4,025

฿4,496 total

includes taxes & fees

15 Nov - 16 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

Luke

฿2,713

฿3,400 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 reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

฿4,873

฿5,443 total

includes taxes & fees

15 Nov - 16 Nov

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

A hallway with a collection of plates on the walls, leading to a staircase.

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.

6. The Porches Inn at Mass MoCA

North Adams

Ram

฿5,297

฿6,671 total

includes taxes & fees

24 Nov - 25 Nov

A living room with a fireplace, two sofas, and four black side tables.

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

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.

7. The Revival House

Adams

Katrina

฿5,067

฿5,660 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

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.

8. Hotel On North

Pittsfield

John

฿4,224

฿4,718 total

includes taxes & fees

8 Nov - 9 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.

9. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

฿5,867

฿6,553 total

includes taxes & fees

27 Oct - 28 Oct

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

A bar area with wooden beams, red chairs, and a long wooden table.

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

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

10. The Williams Inn

Williamstown

Pete

฿6,859

฿7,662 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

11. Jiminy Peak Mountain Resort

Hancock

Olga

฿4,528

฿5,058 total

includes taxes & fees

27 Oct - 28 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.

12. Willows Motel Williamstown

Williamstown

Anuj

฿2,855

฿3,189 total

includes taxes & fees

1 Nov - 2 Nov

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

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

13. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

฿3,376

฿3,771 total

includes taxes & fees

22 Nov - 23 Nov

Two Adirondack chairs facing a river with a forested hill in the background.

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

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

A restaurant interior with white tables, cushioned booths, and a bar area.

14. The Yankee Inn

Lenox

Basil

฿3,579

฿3,998 total

includes taxes & fees

1 Nov - 2 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 room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

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

15. Rodeway Inn

Adams

Joann

฿2,267

฿2,533 total

includes taxes & fees

24 Nov - 25 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 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.

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.

16. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,295

฿3,680 total

includes taxes & fees

15 Nov - 16 Nov

A hotel patio with outdoor seating and a fire pit.

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.

17. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,007

฿4,476 total

includes taxes & fees

15 Nov - 16 Nov

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

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

18. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,702

฿4,135 total

includes taxes & fees

2 Nov - 3 Nov

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

19. Maple Terrace Motel

Williamstown

yeraldine

฿3,343

฿3,734 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

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.

20. Williamstown Motel

Williamstown

Ahmet

฿2,705

฿3,021 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare top hotels in Cheshire

Harbour House Inn Cheshire View	The Springs Motel New Ashford View	Hotel Downstreet, an Ascend Collection Hotel North Adams View	Vacation Village in the Berkshires Williamstown View	Fairfield Inn & Suites by Marriott Williamstown Williamstown View
9.6 Exceptional 58 reviews	9.2 Wonderful 122 reviews	9.0 Wonderful 1,003 reviews	8.8 Excellent 2,797 reviews	8.8 Excellent 438 reviews
฿8,566 ฿9,054 total includes taxes & fees 28 Oct - 29 Oct	฿3,571 ฿3,917 total includes taxes & fees 1 Nov - 2 Nov	฿4,025 ฿4,496 total includes taxes & fees 15 Nov - 16 Nov	฿2,713 ฿3,400 total includes taxes & fees 1 Nov - 2 Nov	฿4,873 ฿5,443 total includes taxes & fees 15 Nov - 16 Nov

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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

Hotel On North

10/10 Excellent

"Perfect for our weekend family trip. Staff was super friendly. Walkable to multiple bakeries/cafes for breakfast. Walls are a little thin so noise can be a problem but otherwise no complaints."

Vacation Village in the Berkshires

10/10 Excellent

"We had a great 2 night stay in a 2 bedroom deluxe suite with our 5-person family for Family Weekend at Williams College, as our daughter just started her college career there. The accommodations were perfect, immaculate, comfortable, spacious and exactly what we needed. We had fun in the pool and playing pool - and the outdoor hotter looked inviting although it was busy so we didn't get into it on this trip. Looking forward to staying again, perhaps when there's some snow on the ground! Highly recommend staying at this lovely resort!"

Quality Inn Lee - Lenox South

8/10 Good

"Bed was comfortable, breakfast was fine, and it's a generally attractive property. We were in room 125, which was awkwardly laid out. The toilet was mashed up against the sink, and the desk was opposite the foot of the bed, making a traffic bottleneck. I'd guess 126 is the same, but hopefully the rest of the rooms weren't."

Berkshire Mountain Lodge

10/10 Excellent

"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every night. If you want an old school meet the other visitors experience, you could probably have it. There is laundry on every floor. I think the awesome prices we got were due to it not being ski season? once we go there and did some driving around we realized Bousquet mountain was right there. So probably a brilliant choice for a long family ski trip. There are a couple of really convenient grocery stores and restaurants right there - but most of the tourist attractions and pittsfield downtown are 10minute or so drive away. Beautiful lobby/property. Enjoyed the coffee machine in the library. Really great experience. We'd love to stay again."

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

10/10 Excellent

"Really excellent spot for families. Loved having a townhouse to spread out and good kitchenette. Amenities were great and helped get little kids energy out."

Jiminy Peak Mountain Resort

8/10 Good

"Rooms were clean, nice beds and new kitchen accessories."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"We enjoyed a delicious home cooked breakfast! The staff was wonderful and very accommodating. Lots of ideas were given to us as to where to visit in the area."

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

8/10 Good

"all good"

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,401

฿2,681 total

27 Oct - 28 Oct

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

฿3,128

฿3,494 total

15 Nov - 16 Nov

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)

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

1055 South Street Pittsfield MA

฿3,208

฿3,583 total

24 Nov - 25 Nov

includes taxes & fees

9.2/10 Wonderful! (246 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

฿3,295

฿3,680 total

15 Nov - 16 Nov

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,579

฿3,998 total

1 Nov - 2 Nov

includes taxes & fees

The Whitlock

16 Church St Lenox MA

฿4,356

฿4,865 total

4 Nov - 5 Nov

includes taxes & fees

8.4/10 Very good! (406 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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Book Hotels in Cheshire on Expedia.com

Find hotels in Cheshire, MA from ฿2,533

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 Revival House

8. Hotel On North

9. The Trail in Adams - Berkshires’ Art Hotel

10. The Williams Inn

11. Jiminy Peak Mountain Resort

12. Willows Motel Williamstown

13. Howard Johnson by Wyndham Williamstown

14. The Yankee Inn

15. Rodeway Inn

16. Best Western Plus Berkshire Hills Inn & Suites

17. Hilton Garden Inn Lenox Pittsfield

18. Hampton Inn & Suites Berkshires-Lenox

19. Maple Terrace Motel

20. Williamstown Motel

Compare top hotels in Cheshire

Harbour House Inn

The Springs Motel

Hotel Downstreet, an Ascend Collection Hotel

Vacation Village in the Berkshires

Fairfield Inn & Suites by Marriott Williamstown

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

Hotel On North

Vacation Village in the Berkshires

Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Jiminy Peak Mountain Resort

The Cornell Inn, Lenox & The Berkshires

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

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Cheshire

FairBridge Inn Express

Quality Inn Lee - Lenox South

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

Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Whitlock

Frequently asked questions

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