The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..

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Vacation Homes in Cheshire

"We enjoyed our stay. Excellent location to explore Western Mass!"

$205 nightly

Oct 28 - Oct 29

Total with taxes and fees

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

$357 nightly

Oct 28 - Oct 29

Total with taxes and fees

"Great property, plenty of space and room for all. Location is ideal"

$456 nightly

Oct 15 - Oct 16

Total with taxes and fees

3 bedrooms, iron/ironing board, WiFi, bed sheets

"as advertised."

$603 nightly

Nov 2 - Nov 3

Total with taxes and fees

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

$449 nightly

Oct 9 - Oct 10

Total with taxes and fees

"Very clean and spacious! We enjoyed our stay with our small pup!"

$437 nightly

Oct 13 - Oct 14

Total with taxes and fees

"Great location, very clean and well appointed with everyth"

$371 nightly

Oct 13 - Oct 14

Total with taxes and fees

"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "

$465 nightly

Oct 9 - Oct 10

Total with taxes and fees

"Kind and responsive host."

$469 nightly

Oct 9 - Oct 10

Total with taxes and fees

$359 nightly

Oct 14 - Oct 15

Total with taxes and fees

"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"

$367 nightly

Oct 9 - Oct 10

Total with taxes and fees

"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...

$271 nightly

Oct 19 - Oct 20

Total with taxes and fees

"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "

$309 nightly

Oct 19 - Oct 20

Total with taxes and fees

"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."

$468 nightly

Nov 2 - Nov 3

Total with taxes and fees

1 bedroom, WiFi, bed sheets, wheelchair access

$233 nightly

Oct 28 - Oct 29

Total with taxes and fees

"Amazing Inn. Cozy and everything we needed. "

$969 nightly

Nov 7 - Nov 8

Total with taxes and fees

5 bedrooms, iron/ironing board, WiFi, bed sheets

$726 nightly

Oct 15 - Oct 16

Total with taxes and fees

$233 nightly

Oct 22 - Oct 23

Total with taxes and fees

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Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Clean venue. Very quiet and I highly recommend renting a kayak. You might see a bald eagle:)"

Jiminy Peak Mountain Resort

10/10 Excellent

"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."

Vacation Village in the Berkshires

10/10 Excellent

"Beautiful property surrounded by the Berkshire mountains. Lovely views of the surrounding area. Be aware there is no late check-out allowed, as I was told it is their policy. I liked the kitchenette and option of the pullout couch although I ended up not needing it. I will definitely be returning to this nice property."

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Cheshire Vacation Homes information

Number of reviews	380
Accommodation	311 Vacation Homes
Lowest Price	$175
Highest Price	$1,047

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Vacation Homes in Cheshire

Berkshire Village Carriage House - Super Private!!

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Sun Filled Lenox Retreat - Minutes to Tanglewood!

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

Bungalow in the Berkshires

NEW RENO Historic Creamery in Berkshires w/hot tub

Comfortable Berkshires retreat on mtn resort, SISO

Riverbend Berkshire East Basecamp - 3 bedrooms available

Near Tanglewood: Historic Summer Retreat

Two Brooks Lodge

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

North Getaway Cottage

Experience Timeless Elegance in The Edith Wharton Room!

Hancock Village Inn at Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Berkshires Untold

The Williams Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Jiminy Peak Mountain Resort

Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Vacation Homes information

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