Cheshire, MA

Cheshire Cove | Waterfront • Kayak • Firepit

2 bedrooms2 beds1 baths4 guests4.9 (38)

About the property

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.

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.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$448Not Available3
Jul 18, 2026$348Available2
Jul 19, 2026$305Available2
Jul 20, 2026$291Available2
Jul 21, 2026$299Not Available4
Jul 22, 2026$293Not Available4
Jul 23, 2026$351Not Available4
Jul 24, 2026$425Not Available4
Jul 25, 2026$438Not Available4
Jul 26, 2026$336Not Available4
Jul 27, 2026$345Not Available4
Jul 28, 2026$314Not Available2
Jul 29, 2026$268Available2
Jul 30, 2026$352Not Available2
Jul 31, 2026$411Not Available2
Aug 1, 2026$448Not Available2
Aug 2, 2026$349Not Available4
Aug 3, 2026$348Not Available4
Aug 4, 2026$359Not Available4
Aug 5, 2026$356Not Available4
Aug 6, 2026$396Not Available3
Aug 7, 2026$479Not Available3
Aug 8, 2026$497Not Available3
Aug 9, 2026$389Not Available2
Aug 10, 2026$359Available2
Aug 11, 2026$351Available2
Aug 12, 2026$361Available2
Aug 13, 2026$404Available2
Aug 14, 2026$477Available3
Aug 15, 2026$447Available3
Aug 16, 2026$362Available3
Aug 17, 2026$374Available3
Aug 18, 2026$447Available3
Aug 19, 2026$369Available3
Aug 20, 2026$395Available3
Aug 21, 2026$473Available3
Aug 22, 2026$463Available3
Aug 23, 2026$401Not Available5
Aug 24, 2026$374Not Available5
Aug 25, 2026$339Not Available5
Aug 26, 2026$332Not Available5
Aug 27, 2026$376Not Available5
Aug 28, 2026$426Not Available5
Aug 29, 2026$426Not Available5
Aug 30, 2026$328Not Available3
Aug 31, 2026$306Available3
Sep 1, 2026$272Available3
Sep 2, 2026$291Available3
Sep 3, 2026$301Available3
Sep 4, 2026$419Available3
Sep 5, 2026$444Available3
Sep 6, 2026$414Available3
Sep 7, 2026$287Available3
Sep 8, 2026$244Available3
Sep 9, 2026$255Available3
Sep 10, 2026$269Available3
Sep 11, 2026$326Available3
Sep 12, 2026$322Not Available3
Sep 13, 2026$232Not Available7
Sep 14, 2026$221Not Available7
Sep 15, 2026$231Not Available7
Sep 16, 2026$222Not Available7
Sep 17, 2026$245Not Available7
Sep 18, 2026$279Not Available7
Sep 19, 2026$287Not Available7
Sep 20, 2026$264Not Available4
Sep 21, 2026$261Available4
Sep 22, 2026$272Available4
Sep 23, 2026$265Available4
Sep 24, 2026$289Available4
Sep 25, 2026$356Available4
Sep 26, 2026$345Available4
Sep 27, 2026$272Available4
Sep 28, 2026$253Available4
Sep 29, 2026$265Available4
Sep 30, 2026$265Available4
Oct 1, 2026$302Available4
Oct 2, 2026$387Available4
Oct 3, 2026$378Available4
Oct 4, 2026$297Available4
Oct 5, 2026$251Available4
Oct 6, 2026$248Available4
Oct 7, 2026$305Available4
Oct 8, 2026$317Available4
Oct 9, 2026$499Available4
Oct 10, 2026$499Available4
Oct 11, 2026$499Available4
Oct 12, 2026$352Available4
Oct 13, 2026$314Available5
Oct 14, 2026$340Available5
Oct 15, 2026$323Available5

Amenities

Waterfront
Fire pit
Outdoor fireplace
Fire place
Patio
Balcony
Mountain view
Lake view

4.9 · 38 reviews

N
Nate
3 days ago

I stayed here in late June 2026 (meeting friends at Solid Sound in North Adams). This is a beautiful small home that has been renovated in a modern, tasteful style. It’s well appointed with everything you need. The main feature is the location: literally steps from the gorgeous Cheshire Reservoir. It is extremely quiet and peaceful here and an absolute pleasure to sit outside and be surrounded by natural beauty. There’s plenty of seating outside, a fire pit, and a grill. And a paddle boat and kayaks! If you need supplies there is a Target only 15 minutes away. 25 minutes north is Mass MoCA, an outstanding modern art museum. Other than that, there are countless natural areas to explore all around this location. Jaryn was an amazing host. Very responsive with any questions or concerns. Easy check in / check out. I would absolutely stay here again!

M
Malin
6 days ago

Great place to relax! Very clean and comfortable beds. My son loved the kayak and the paddle boat. Watching the bald eagles on the little island in the lake was a big plus. We want to come back!

I
Ivy B.
2 weeks ago

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!!

Where you'll be

Cheshire, MA, 01225, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 11:00 AM.
Maximum 4 guests.