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Cheshire Cove | Waterfront • Kayak • Firepit

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A room with a sliding glass door leading to a deck with a view of a lake, a chair, and a white door.
A modern kitchen with a central island, white cabinetry, and a stone accent wall.
A kitchen with a stone accent wall, a bar area with stools, and pendant lighting.
A modern living room with a dining table, a sofa, and a kitchen area in the background.
A lakeside outdoor seating area with Adirondack chairs and a fire pit.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroom

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Cheshire, MA
  • Place, Cheshire Reservoir
    ‪1 min walk‬
  • Place, Jiminy Peak Mountain Resort
    ‪26 min drive‬
  • Place, Tanglewood Music Center
    ‪40 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪33 min drive‬

Room options

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About the neighborhood

Cheshire

With a stay at this vacation home in Cheshire, you'll be on the waterfront, just steps from Cheshire Reservoir and a 4-minute drive from St Mary's of the Assumption Church. .This vacation home is 10.6 mi (17.1 km) from Jiminy Peak Mountain Resort and 3.5 mi (5.6 km) from Mount Greylock State Reservation.
View more Vacation Homes in CheshireOpens in a new window

What's nearby

  • Cheshire Reservoir - 1 min walk - 0.1 miles
  • Jiminy Peak Mountain Resort - 26 min drive - 12.8 miles
  • Williams College - 35 min drive - 22.7 miles
  • Tanglewood Music Center - 40 min drive - 20.7 miles
  • Mount Greylock - 52 min drive - 18.1 miles

Getting around

  • Pittsfield Station - 16 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 31 min drive

Restaurants

  • ‪McDonald's - ‬11 min drive
  • ‪Chipotle Mexican Grill - ‬13 min drive
  • ‪Viking Pub - ‬10 min drive
  • ‪Applebee's Grill + Bar - ‬13 min drive
  • ‪Cumberland Farms - ‬16 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Cheshire Cove | Waterfront • Kayak • Firepit

Escape to this charming lakeside oasis on Cheshire Lake in the heart of The Berkshires. This nicely appointed 2-bedroom, 1-bath home offers stunning water views, a warm indoor fireplace, and a spacious deck perfect for relaxing or dining outdoors. Enjoy kayaking right from the backyard, grilling al fresco, or cooking up some s`mores at the fire pit. Whether you seek tranquility or adventure, this spot is your perfect lakeside escape, book now before it`s too late!

✔ High-speed Wi-Fi
✔ Smart TV
✔ Fully equipped kitchen
✔ Indoor fireplace
✔ Washer & dryer
✔ Free parking
✔ Spacious deck
✔ Kayak & Pedal boat
✔ Firepit & Outdoor grill
✔ Pack n Play Travel Crib (Upon request)

➥ 8 mins to Ashuwillticook Rail Trail
➥ 13 mins to Mount Greylock State Reservation Visitor Center
➥ 17 mins to Jiminy Peak Mountain Resort
➥ 18 mins to Berkshire Museum
➥ 18 mins to The Colonial Theatre: Berkshire Theatre Group
➥ 21 mins to MASS MoCA
➥ 25 mins to Bousquet Mountain Ski Area
➥ 26 mins to Hancock Shaker Village

✦BEDS & BATHS✦
Inside we have 2 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience.

Room Breakdown:
Main Bedroom - 1 Queen bed
Bedroom 2 - 1 King bed

All Berkshire Vacation Rental Co.™ Properties include:
- Support from full-time local team available daily from 9am to 9pm
- Professional housekeeping & property inspection prior to guest arrival
- Towels, linens, and bath products
- At least a mornings worth of coffee to get you started
- Learn more @berkshirevacationrental

Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.

No pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.

To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.

Parking at this property is tight. There is a designated spot that will fit two cars snugly. Absolutely no parking on the front lawn, septic system will get crushed.
As hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return.
no smoking
no overnight guests beyond those outlined in the booking
no parties
please respect all quiet hours
Please see guest packet for more information.
Make yourself comfortable in this vacation home, which features a fireplace and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like onsite parking.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden

Laundry

  • Washing machine

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • On a lake
  • On the waterfront

Things to do

  • Kayak

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM

Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Rules

As hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. no smoking

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number c0541830580

We should mention

A car is not required for transportation to and from this property

Property is also known as

417729

Cheshire Cove | Waterfront • Kayak • Firepit Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Ivy

Liked: Cleanliness, check-in, communication, listing accuracy
We loved our stay at this house in Cheshire. It is right on Cheshire Lake. It was so peaceful - we swam and used the kayaks provided right from the back yard. We even saw a bald eagle on the lake !!! The house is immaculate with a well stocked kitchen that we cooked in and beautiful new washer and dryer we used. The living room is very comfortable with nice TV and games. The house is just a few minutes from great hiking at Mt Greylock and other trails. And good options for buying supplies and eating out all within a few minutes drive. Can’t wait to stay there again!!
Stayed 2 nights in Jun 2026

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