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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Compare 70 Cottages in Cheshire with updated reviews, rates, and availability.

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

"Excellent property: would have liked to stay longer. "

"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"

"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."

"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."

"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "

"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...

"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "

"Very nice house. Owners very helpful."

"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "

House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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Other property types in Cheshire

Indoor pool, outdoor pool, pool umbrellas

"The property was clean and the staff very accommodated."

AED 490 total

includes taxes & fees

12 May - 13 May

"Out dated not many resort like options "

AED 545 total

includes taxes & fees

12 May - 13 May

"Very comfortable property in a lovely setting "

Recent reviews of Cheshire hotels

The Constance, The Whitlock, & The Dewey By The Lenox Collection

5/5 Excellent

"We highly recommend this place to stay. Absolutely wonderful experience. ❤️"

A verified traveler stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection

Posted 23 hours ago

5/5 Excellent

"A delightful property in every way. We had comfy beds, lots of quiet (our rooms were adjacent to the elevator and we never heard a peep), loved the complimentary coffee, tea, and water. Enjoyed the public spaces and the restaurant. Easy parking, steps from Spring Street. I could go on and on, but the summary is I’d be so pleased to stay here again. "

A verified traveler stayed at The Williams Inn

Posted 4 days ago

5/5 Excellent

"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, which was quite noisy and inconvenient as it was right next to our room. Additionally, the lobby was not accessible at the time, which was a bit disappointing. Despite these minor issues, my overall experience was positive, largely thanks to the excellent staff and comfortable accommodations."

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham

Posted 4 days ago

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Search Cottages in Cheshire

Check prices for these dates

Compare 70 Cottages in Cheshire with updated reviews, rates, and availability.

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Family-Friendly Richmond Cottage w/ Private Yard

Family-Friendly Richmond Cottage w/ Private Yard

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, walking distance to lake

Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Beachwood Cottage

Beachwood Cottage

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Picturesque Cottage with Sunroom on Ashmere Lake!

Picturesque Cottage with Sunroom on Ashmere Lake!

Cozy Berkshire cottage with fireplace.

Cozy Berkshire cottage with fireplace.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Plan your Berkshires by the lake

Plan your Berkshires by the lake

Cottage in the Clouds With Mountain Views

Cottage in the Clouds With Mountain Views

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!

Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!

Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!

Other property types in Cheshire

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

The Ponds at Foxhollow

The Ponds at Foxhollow

Recent reviews of Cheshire hotels

Recent reviews of Cheshire hotels

The Constance, The Whitlock, & The Dewey By The Lenox Collection

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Popular Destinations

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