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Vacation rentals in Cheshire

Vacation rentals in Cheshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cheshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Berkshires Waterfront Lakehouse
    Entire cottage · 6 guests · 4 beds · 1.5 bathrooms
    Berkshires Waterfront Lakehouse

    Fully furnished , totally remodeled ( completed in Feb. 2016), lakefront home set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere.

    What guests are saying:

    “Perfect getaway place with beautiful surroundings. Quarantine? No problem, you can enjoy everything in David’s lake house from fire pit, hot tub, and luxurious interiors. Just a few minutes distance from local stores, Target, Walmart so can’t complain.”

  • Berkshire Guest Suite
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Berkshire Guest Suite

    Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

    What guests are saying:

    “We were very pleased with our stay at Dave and Ashley’s. We had done some hiking in the area and we were far enough from home where we made a fun little trip out of it to stay in the area for the night. Very beautifully decorated and comfortable. Great added touches with snacks, coffee, mini fridge, toiletries, TV, and more. Beautiful neighborhood and view of the mountains. Will definitely be back in the future!”

  • 19th c. Renovated Barn in the Berkshires
    SUPERHOSTEntire house · 8 guests · 8 beds · 1 bathroom
    19th c. Renovated Barn in the Berkshires

    Mason Hill is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, an historic restored barn and outbuildings surrounded by lush forest. Mason Hill is the perfect year-round getaway for any traveler.

    What guests are saying:

    “Jane and Ian’s Red Barn was an absolutely wonderful Air BnB stay. We were in town for a wedding, Jane and Ian were kind enough to let the Bridal party use the space to get ready. The space was both beautiful and practical, I can’t wait to see the pictures. I highly recommend booking this space if you will be visiting the area, you will not regret it. I just wish we stayed an extra day to hang out, and play some board games. 11 out of 10 stars.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Cheshire holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cheshire

Cozy cottage in the Berkshires
SUPERHOSTEntire cottage
Cozy cottage in the Berkshires
Price:€129 / night
BEAUTIFUL LOG HOME
SUPERHOSTEntire house
BEAUTIFUL LOG HOME
Price:€121 / night
The Camp - 20 Minutes to Berkshire East!
SUPERHOSTEntire cabin
The Camp - 20 Minutes to Berkshire East!
Price:€70 / night
Rent a cottage
Entire cottage
Rent a cottage
Price:€76 / night
Two room suite and home to Colonial Alpacas.
SUPERHOSTPrivate room
Two room suite and home to Colonial Alpacas.
Price:€71 / night
Private Cottage in the Berkshires
SUPERHOSTEntire guest house
Private Cottage in the Berkshires
Price:€87 / night
Honeysuckle Rose Cottage
Entire house
Honeysuckle Rose Cottage
Price:€65 / night
Pollard Apartment in walking distance to Mass MoCA
SUPERHOSTEntire flat
Pollard Apartment in walking distance to Mass MoCA
Price:€74 / night
Private Paradise in the Berkshires
SUPERHOSTEntire cabin
Private Paradise in the Berkshires
Price:€129 / night
Spacious Duplex in Heart of the Berkshires
SUPERHOSTEntire house
Spacious Duplex in Heart of the Berkshires
Price:€124 / night
The Sail Loft
SUPERHOSTEntire cottage
The Sail Loft
Price:€78 / night
Berkshire Cottage at Ashmere Lake
SUPERHOSTEntire cottage
Berkshire Cottage at Ashmere Lake
Price:€127 / night
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