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 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 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

6.570.323 ₫

6.944.832 ₫ 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 hotel room with a large bed, a desk, a chair, and a view of the outdoors.

2. The Springs Motel

New Ashford

Elizabeth

2.737.339 ₫

3.002.861 ₫ total

includes taxes & fees

1 Nov - 2 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.

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

3. Vacation Village in the Berkshires

Williamstown

Adrianne

2.080.697 ₫

2.608.240 ₫ total

includes taxes & fees

1 Nov - 2 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 room with a hanging bed, a white wall, a window, and a door.

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.

4. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

4.497.519 ₫

5.023.729 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

5. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

3.087.042 ₫

3.448.227 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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 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.

6. The Revival House

Adams

Katrina

3.573.942 ₫

3.991.985 ₫ total

includes taxes & fees

5 Nov - 6 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 restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

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

7. Jiminy Peak Mountain Resort

Hancock

Olga

3.472.922 ₫

3.879.253 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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 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.

8. FairBridge Inn Express

Pittsfield

Richard

1.841.348 ₫

2.056.786 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

A rectangular swimming pool with a wooden deck surrounding it.

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.

9. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

2.847.091 ₫

3.180.231 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

10. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

3.737.599 ₫

4.174.899 ₫ total

includes taxes & fees

15 Nov - 16 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.

11. Hotel On North

Pittsfield

Devon

3.472.922 ₫

3.879.254 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A person lying on a bed with a book, in a room with a red wall and a lamp in the background.

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

12. The Porches Inn at Mass MoCA

North Adams

Ram

4.172.168 ₫

5.238.907 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

A spacious living area with a fireplace, wooden beams, and a large window.

13. The Williams Inn

Williamstown

Joshua

5.261.179 ₫

5.876.737 ₫ 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 single-story building with a porch, a chimney, and a satellite dish.

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

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

14. Rodeway Inn

Adams

Joann

1.739.043 ₫

1.942.511 ₫ total

includes taxes & fees

3 Nov - 4 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 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.

15. The Yankee Inn

Lenox

Basil

2.745.188 ₫

3.066.375 ₫ 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 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 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

James

2.527.127 ₫

2.822.801 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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.

17. Willows Motel Williamstown

Williamstown

David

2.189.676 ₫

2.445.807 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

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

A motel with a parking lot, a swimming pool, and outdoor seating.

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

18. Berkshire Inn

Pittsfield

cheryl

2.226.969 ₫

2.487.525 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

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

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

19. The Central Downtown Inn & Suites

Pittsfield

Debra

2.562.615 ₫

2.862.363 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

20. Berkshire Mountain Lodge

Pittsfield

Joel

2.240.942 ₫

3.081.693 ₫ total

includes taxes & fees

10 Nov - 11 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

The Williams Inn

10/10 Excellent

"Fantastic hotel! Would definitely stay again."

The Yankee Inn

10/10 Excellent

"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."

Vacation Village in the Berkshires

8/10 Good

"I liked the location and the room itself very much. I thought the price was good too. Only real complaint is the pool is very busy and smallish for the amount of families the place can hold. Also, the pool isnt connected from what i could tell so you have to drive or take a walk to and from your roomafrom i"

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."

Berkshires Untold

10/10 Excellent

"Had a great time enjoying the outdoor space, the bar, and the "living room" area by the fire. Although our room was on the highway side so could hear traffic, we had a gorgeous view of the mountains and changing foliage. Would go back"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The unit was clean and comfortable. Location was nice and quiet. Mini golf and hot tub were fun and appreciated. Unit was dated- cabinets were old. Kitchen was well- stocked. I would suggest having kitchen towels though. Blankets would have been nice ( as the weather was changing.)."

Hotel On North

10/10 Excellent

"Well maintained and updated property. Very kind and helpful team."

Jiminy Peak Mountain Resort

8/10 Good

"Cuisine bien équipée beau site. Un peu vieillot. La porte du lave vaisselle était brisée mais il fonctionnait tout de même bien. On avait un bac avec sel et poivre et sucre en plus que des filtres et sachets à café. Un beau gros four/air fryer dans la chambre également qui était très pratique. Des couverts pour 6 personnes.Jy retournerais sans hésitation . Le lit était confortable. Les oreillers un peu moins"

More cheap stays in Cheshire

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.841.348 ₫

2.056.786 ₫ total

21 Oct - 22 Oct

includes taxes & fees

5.4/10 (925 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.044.915 ₫

2.284.170 ₫ total

22 Oct - 23 Oct

includes taxes & fees

7.6/10 Good! (929 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

2.399.450 ₫

2.680.186 ₫ total

9 Nov - 10 Nov

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

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

1055 South Street Pittsfield MA

2.460.310 ₫

2.748.167 ₫ total

17 Nov - 18 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.745.188 ₫

3.066.375 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

3.599.822 ₫

4.021.001 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (402 reviews)

Hotels in Cheshire with star rating

Frequently asked questions

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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More ways to book

Book Hotels in Cheshire on Expedia.com

Find hotels in Cheshire, MA from 1.942.511 ₫

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. Vacation Village in the Berkshires

4. The Trail in Adams - Berkshires’ Art Hotel

5. Hotel Downstreet, an Ascend Collection Hotel

6. The Revival House

7. Jiminy Peak Mountain Resort

8. FairBridge Inn Express

9. Howard Johnson by Wyndham Williamstown

10. Fairfield Inn & Suites by Marriott Williamstown

11. Hotel On North

12. The Porches Inn at Mass MoCA

13. The Williams Inn

14. Rodeway Inn

15. The Yankee Inn

16. Best Western Plus Berkshire Hills Inn & Suites

17. Willows Motel Williamstown

18. Berkshire Inn

19. The Central Downtown Inn & Suites

20. Berkshire Mountain Lodge

Stay near popular Cheshire attractions

St Mary's of the Assumption Church

Learn more about Cheshire

Top Cheshire Hotel Reviews

The Williams Inn

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

Vacation Village in the Berkshires

Hampton Inn & Suites Berkshires-Lenox

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

Jiminy Peak Mountain Resort

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

Hotels in Cheshire with star rating

Frequently asked questions

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