Cheshire Vacation Rentals from ₩154,340: Search Short-Term Rentals

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Our top choices for Cheshire vacation rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Williamstown

Alex

₩163,718 total

includes taxes & fees

Sep 2 - Sep 3

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

2. Berkshire Mountain Lodge

Pittsfield

Robert

₩154,340 total

includes taxes & fees

Oct 1 - Oct 2

A wooden cabin with a covered deck, a fire pit, and string lights.

3. Huttopia Berkshires

Williamstown

GEORGINA

₩149,434 total

includes taxes & fees

Sep 8 - Sep 9

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

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

₩762,712 total

includes taxes & fees

Sep 1 - Sep 2

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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Best buy in the area during the high season. Spacious room and great location. Only negative is that property is a bit dated but recent renovations have been made."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Quality Inn Lee - Lenox South

8/10 Good

"Very nice and clean motel...better than I thought it would be, so we felt a lot better about staying there. We were a bit disappointed about the breakfast portion of the day so went out for brunch instead. The breakfast sandwiches weren't that great and not many tables to sit at. But overall, the rooms and bathrooms were very clean and modern."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Find out more about Cheshire

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Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

How many vacation rentals are there in Cheshire?

Expedia has 5 vacation rentals for your stay in Cheshire.

What can I see and do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.

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Check prices for these dates

Our top choices for Cheshire vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. Huttopia Berkshires

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

Berkshires Untold

The Red Lion Inn

Find out more about Cheshire

Frequently asked questions

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