Cheshire Holiday Homes from £148: Search Holiday Homes in Cheshire

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire holiday homes

1. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

includes taxes & fees

24 Sept - 25 Sept

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

2. Cozy Home in Pownal VT

Pownal

Jess M.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

3. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

includes taxes & fees

24 Sept - 25 Sept

A wooden deck with a table and chairs, surrounded by a white railing.

4. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Diego G.

includes taxes & fees

24 Sept - 25 Sept

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

6. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

includes taxes & fees

27 Sept - 28 Sept

A kitchen with white cabinets, a wooden dining table, and pendant lights.

7. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

includes taxes & fees

13 Oct - 14 Oct

A spacious living room with a dining area, a kitchen, and a large window.

8. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

9. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

includes taxes & fees

29 Sept - 30 Sept

A white two-story house with a porch, surrounded by trees and a hill.

10. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

includes taxes & fees

5 Oct - 6 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

11. The Greylock Cabin

Florida

Margaret M.

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a porch, surrounded by trees and snow.

12. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

includes taxes & fees

29 Sept - 30 Sept

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

13. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

includes taxes & fees

28 Sept - 29 Sept

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

14. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

28 Sept - 29 Sept

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

includes taxes & fees

27 Sept - 28 Sept

A flat landscape with a clear sky and distant hills.

16. Ellie’s Overlook, best view in the Berkshires!

Richmond

includes taxes & fees

28 Sept - 29 Sept

A hallway with wooden flooring, white walls, and a bed in the background.

17. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

includes taxes & fees

28 Sept - 29 Sept

A red house with a porch, surrounded by a grassy yard and trees.

18. Two Brooks Lodge

Bennington

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

Hunter

includes taxes & fees

29 Sept - 30 Sept

An aerial view of a house surrounded by a forest with autumn foliage.

19. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

includes taxes & fees

6 Oct - 7 Oct

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

20. NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

Anonymous traveller

includes taxes & fees

29 Sept - 30 Sept

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Top Cheshire Hotel Reviews

The Yankee Inn

10/10 Excellent

"Everything, delicious free breakfast, hot showers, plenty of room, outdoor patio w Adirondack chairs, pleasant staff, very clean place. Fabulous price! I would not hesitate to return to this place."

Berkshire Mountain Lodge

8/10 Good

"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."