Cheshire Cove | Waterfront • Kayak • Firepit

Exterior

Patio

Garden

Balcony

Living Room

Kitchen

Bedroom 1

Bedroom 2

Ensuite Bathroom

Common Area

Laundry Room

Cheshire, MA

Cheshire Cove | Waterfront • Kayak • Firepit

2 bedrooms 2 beds 1 baths 4 guests

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 and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. 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 and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. 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

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Apr 18, 2026$169Not Available3
Apr 19, 2026$156Not Available2
Apr 20, 2026$135Not Available2
Apr 21, 2026$135Not Available2
Apr 22, 2026$169Not Available2
Apr 23, 2026$153Available2
Apr 24, 2026$188Not Available2
Apr 25, 2026$186Not Available2
Apr 26, 2026$179Not Available3
Apr 27, 2026$187Not Available3
Apr 28, 2026$191Not Available2
Apr 29, 2026$185Available2
Apr 30, 2026$196Available2
May 1, 2026$244Available2
May 2, 2026$208Available2
May 3, 2026$196Available2
May 4, 2026$181Available2
May 5, 2026$189Available2
May 6, 2026$182Available2
May 7, 2026$204Available2
May 8, 2026$214Available2
May 9, 2026$217Available2
May 10, 2026$206Available2
May 11, 2026$198Available2
May 12, 2026$211Available2
May 13, 2026$150Not Available5
May 14, 2026$162Not Available5
May 15, 2026$177Not Available5
May 16, 2026$185Not Available5
May 17, 2026$177Not Available5
May 18, 2026$150Not Available5
May 19, 2026$151Not Available5
May 20, 2026$154Not Available5
May 21, 2026$183Not Available5
May 22, 2026$242Not Available5
May 23, 2026$242Not Available5
May 24, 2026$237Not Available5
May 25, 2026$154Not Available5
May 26, 2026$154Not Available5
May 27, 2026$230Not Available3
May 28, 2026$259Not Available4
May 29, 2026$260Not Available4
May 30, 2026$276Not Available4
May 31, 2026$244Not Available4
Jun 1, 2026$235Not Available3
Jun 2, 2026$229Available3
Jun 3, 2026$245Available3
Jun 4, 2026$300Available3
Jun 5, 2026$331Available3
Jun 6, 2026$335Available3
Jun 7, 2026$298Available3
Jun 8, 2026$302Available3
Jun 9, 2026$304Available3
Jun 10, 2026$362Available3
Jun 11, 2026$545Available3
Jun 12, 2026$550Available3
Jun 13, 2026$548Available3
Jun 14, 2026$314Available3
Jun 15, 2026$275Available4
Jun 16, 2026$286Available4
Jun 17, 2026$257Available4
Jun 18, 2026$293Available4
Jun 19, 2026$318Available4
Jun 20, 2026$308Available4
Jun 21, 2026$253Available4
Jun 22, 2026$233Available4
Jun 23, 2026$236Available4
Jun 24, 2026$298Available4
Jun 25, 2026$413Available4
Jun 26, 2026$599Available4
Jun 27, 2026$599Available4
Jun 28, 2026$470Available4
Jun 29, 2026$305Available4
Jun 30, 2026$245Available4
Jul 1, 2026$302Available4
Jul 2, 2026$442Available4
Jul 3, 2026$509Available4
Jul 4, 2026$467Available4
Jul 5, 2026$335Available4
Jul 6, 2026$262Available4
Jul 7, 2026$263Available4
Jul 8, 2026$267Available4
Jul 9, 2026$340Available4
Jul 10, 2026$397Available4
Jul 11, 2026$402Available4
Jul 12, 2026$304Available4
Jul 13, 2026$311Available4
Jul 14, 2026$315Available4
Jul 15, 2026$315Available5
Jul 16, 2026$337Available5
Jul 17, 2026$402Available5

Where you'll sleep

Amenities

Kayaks
Fire pit
BBQ Area
Patio
Lake view
BBQ Utensils
Outdoor seating
Outdoor dining area

Guests love this place

4.71

based on 14 reviews

V
Victor G.
about 2 months ago

Nice place, nice host, very conveniently situated and very cozy, we had a great time and recommend !

A
Arty P.
about 2 months ago

Nice structure. Two major problems. One being water pressure. You can barely get wet in shower, you certainly can’t when dishwasher is on as there is no water at all in that circumstance. Secondly there is no parking unless you drive a Prius or a jeep.

C
Claire C.
about 2 months ago

We celebrated Christmas 2025 with our son and grandson. We’re surprised with a sneak snowstorm which made everything that much more special. We were even shoveled out, very nice touch. Plan to visit in the summer.

Where you'll be

Cheshire, MA, 01225, United States of America

Explore the scenic heart of the Berkshires from this refined escape positioned near the majestic peaks of Western Massachusetts. A short drive away, Mount Greylock State Reservation offers expansive vistas and rugged hiking trails, while Whitney’s Farm Market & Garden Center provides a charming stop for fresh deli provisions. Discover the Ashuwillticook Rail Trail for a morning cycle or venture within easy reach of Wahconah

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.
Fair-Refund policy applies after the cancellation deadline.

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.