Cheshire Vacation Rentals from ￥12,898: Search Short-Term Rentals

Q: What's the top vacation rental that Cheshire has to offer?

Spacious 5-bedroom house in charming Lee with WiFi : Visitors like this Cheshire vacation home rental. It offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

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Vacation Rentals in Cheshire

"Great stay with all plenty of things to do…"

￥16,036 total

includes taxes & fees

Aug 25 - Aug 26

"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"

￥29,688 total

includes taxes & fees

Jul 31 - Aug 1

"A good place for vacation that you can enjoy and rest. Very nice and safe place."

￥20,235 total

includes taxes & fees

Aug 27 - Aug 28

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

￥123,228 total

includes taxes & fees

Aug 11 - Aug 12

"Such a sweet spot in the woods! Can’t wait to come back."

￥24,392 total

includes taxes & fees

Jul 31 - Aug 1

"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."

￥26,370 total

includes taxes & fees

Jul 31 - Aug 1

"Very friendly hosts, great location. "

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"Loved the property. Perfect for our gathering."

"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."

￥21,394 total

includes taxes & fees

Aug 10 - Aug 11

"Very kinda hosts, and wonderful house."

￥153,680 total

includes taxes & fees

Aug 4 - Aug 5

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

￥51,155 total

includes taxes & fees

Aug 3 - Aug 4

"Highly recommend this charming, historic place. Well appointed. Has everything you need for your stay. Cozy…yet plenty of space for everyone. Looks like it was just renovated. Took my daughter and two granddaughters for a ski weekend. Wouldn’t hesitate to come back here. "

"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."

"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."

"Kind and responsive host."

￥71,964 total

includes taxes & fees

Jul 31 - Aug 1

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

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Top Cheshire Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Loved our visit"

FairBridge Inn Express

6/10 Okay

"Well the little fridge they had in the room hummed loudly all the time the freezer needed to be defrosted I bought a couple of frozen dinners and couldn't get both of them in the freezer. One of the draws on the side tables when I pulled open the drawer one side of the handle came loose I was able to screw it back in but it needed a screwdriver to tighten it up all small little things but a inconvenience none the less"

Find out more about Cheshire

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cheshire!

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.

What's the top vacation rental that Cheshire has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: Visitors like this Cheshire vacation home rental. It offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly.

What can I see and do in Cheshire?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. 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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Cheshire Vacation Rentals

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Vacation Rentals in Cheshire

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

The Ponds at Foxhollow

Huttopia Berkshires

Spacious 5-bedroom house in charming Lee with WiFi

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Timber Trails Unique cabin experience

Contemporary Berkshire Home with Views of Taconic Golf Course

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

The Kemble- Built by a US Secretary of State in Lenox

Deluxe Queen Room with 2 Queen Beds

Hancock Village Inn at Jiminy Peak

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

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Charming Berkshires Retreat – Minutes to Williamstown

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Comfortable Berkshires retreat on mtn resort, SISO

The Clearing - Quiet - Close To Nature

Quintessential 6-BR Berkshires Lodge

Top Cheshire Hotel Reviews

The Red Lion Inn

The Yankee, Trademark Collection by Wyndham

Hotel Downstreet, Ascend Hotel Collection

The Constance by the Lenox Collection

The Williams Inn

FairBridge Inn Express

Berkshire Mountain Lodge

Berkshires Untold

Quality Inn

Find out more about Cheshire

Frequently asked questions