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Cheshire, MA vacation rentals
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Cheshire, MA Vacation rentals: no available offers. Here are other great options for your stay!

Cozy Cottage In Berkshires: Minutes To Jiminy Peak - Cheshire, MA
9.9 77 reviews
Cheshire, MA
08/28 – 08/30
$460/nighttotal: $920 (2 )

Cozy Cottage In Berkshires: Minutes To Jiminy Peak

4 6
apartment , Lanesborough
This Lanesborough apartment is located in a quiet residential neighborhood at the top of a hill, just 1 mile from the Ashuwillticook Rail Trail and less than a mile from Elle Day Spa. The 4-bedroom home can accommodate up to 6 guests and offers a spacious backyard with a fire pit, a cozy sunken sunroom with a fireplace, and mountain views.
Jiminy Peak Slopeside Getaway • Ski & Adventure - Cheshire, MA
10 9 reviews
Cheshire, MA
08/28 – 08/30
$460/nighttotal: $920 (2 )

Jiminy Peak Slopeside Getaway • Ski & Adventure

1 6
house , Hancock
This slopeside condo in Hancock offers ski-in/ski-out access, a 3-minute walk to the Jiminy Peak chair lift, and is within a 20-mile radius of Ramblewild Adventure Park and Mass MoCA.
This 2-bedroom, 2-bathroom unit accommodates up to 7 guests, featuring a full kitchen with modern appliances, a fireplace, a Smart TV, a private porch and deck, in-unit laundry, and access to resort amenities including a heated pool and hot tub.
Greylock View Cottage - Cheshire, MA
10 9 reviews
Cheshire, MA
08/30 – 09/06
$234/nighttotal: $1638 (7 )

Greylock View Cottage

1 2
apartment , Adams
Greylock View Cottage, a one-bedroom apartment in Adams, MA, boasts spectacular Mount Greylock views and a private backyard bordering acres of woods.
This recently renovated rental features a queen bed, a twin daybed, a full kitchen with dishwasher, in-unit laundry, air conditioning, WiFi, and parking for up to three guests.
Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous - Cheshire, MA
9.6 34 reviews
Cheshire, MA
08/28 – 08/30
$517/nighttotal: $1034 (2 )

Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous

2 6
apartment , Hancock
This Hancock apartment offers ski-in/ski-out access and is 0.1 miles from Jiminy Peak Mountain Resort. It's within 9 miles of Zema's Nursery, Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Brodie Mountain. It has an excellent user rating.
The apartment has two bedrooms, one bathroom, and a sofa bed. It can accommodate up to 8 guests and has a floor area of 900 square feet. It features a kitchen with a refrigerator and oven, a fireplace, a DVD player, and air conditioning. Guests have access to a fitness center, a swimming pool, a Jacuzzi, and parking.

Frequently Asked Questions about vacation rentals in Cheshire, MA

  • What sports or outdoor activites can visitors enjoy in and around Cheshire, MA?

    Cheshire is a great place for hiking, fishing, and kayaking. You can hike the trails at Mount Greylock State Reservation, fish in the nearby Hoosac River, or kayak on the scenic Lake Garfield. For those who enjoy winter activities, there's cross-country skiing and snowshoeing at Mount Greylock.
  • What are the best Airbnb and vacation rentals in Cheshire, MA?

    19th C - Barn In The Berkshires, Berkshires Lakefront Retreat On 4 Private Acres and The Berkshires Hummingbird House are the most popular Airbnb and vacation rentals in Cheshire, MA among travelers.

  • What other towns or cities can be easily accessed from Cheshire, MA?

    Cheshire is conveniently located near several other towns and cities. You can easily drive to Adams, North Adams, and Williamstown, all within a 15-20 minute drive. If you're looking for a bigger city, Pittsfield is about a 30-minute drive from Cheshire.
  • What are the most popular Airbnbs in Cheshire, MA?

  • What amenities are commonly available in vacation rentals in Cheshire, MA?

    Vacation rentals in Cheshire often come with amenities like kitchens, laundry facilities, and outdoor spaces. Some rentals may also have fireplaces, hot tubs, or even private access to a lake or river.
  • What are the best rentals for families and kids in Cheshire, MA?

  • What time of year is best to rent a vacation rental Cheshire, MA?

    The best time to visit Cheshire depends on your preferences. Spring and fall offer mild weather and beautiful foliage, while summer is ideal for outdoor activities. Winter brings snow and ice, perfect for those who enjoy winter sports.
  • What are the local dishes in Cheshire, MA region?

    The region is known for its hearty New England cuisine. You'll find plenty of traditional dishes like clam chowder, lobster rolls, and New England boiled dinners. Local farms also produce delicious fruits and vegetables, so be sure to try some fresh produce while you're here.

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