Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
4 bedrooms2+ bathroomsSleeps 8
Popular amenities
Onsite parking available
Dog-friendly
Kitchen
Washer/dryer
Air-conditioning
Balcony or patio
Explore the area
Cheshire, MA
St Mary's of the Assumption Church
Place, St Mary's of the Assumption Church
3 min drive
Mount Greylock State Reservation
Place, Mount Greylock State Reservation
7 min drive
Skyline Country Club
Place, Skyline Country Club
15 min drive
Pittsfield, MA (PSF-Pittsfield Municipal)
Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
33 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 Double Sofa Bed
Bedroom 2
1 Single Bunk Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Queen Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Kitchen
Office
Garden
Dining area
About this property
Berkshires Lakefront Retreat by Evergreen Home
Evergreen Home Vacation Rentals invites you to this serene retreat on 4 private acres, just 15 minutes from Jiminy Peak. This newly renovated 4BR/2.5BA home offers breathtaking views of both the lake and mountains.
Discover a chef’s dream kitchen with top-tier appliances, perfect for culinary creativity. After a day of adventure, unwind in the luxurious soaking tub or relax by the fire. Whether seeking peace or mountain thrills, this is your perfect Berkshire escape.
If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.
This beautiful lake front property in Cheshire provides breathtaking views year round. The large property provides plenty of privacy for a relaxing stay.
Guests have access to the entire home. A golf cart is also available for an easy ride down to the lakefront.
For chefs enjoying the bounty of the Berkshires & the Hudson Valley, the main floor of this home features a fully stocked chef’s kitchen with quartz countertops, professional cooktop, and wall oven. There is even a sous vide immersion circulator for your use! A Nespresso coffee/cappuccino machine is provided to make your favorite coffee shop beverage at home!
A dining area in the kitchen provides counter seating for four guests while the main dining room seats an additional six people. Cozy up in the living room with a gas fireplace and a 65” smart TV with surround sound. The first floor also contains a half bath.
The primary suite features a balcony overlooking the property and huge windows offering views of the lake and mountains beyond. Sleep soundly on a King memory foam mattresses and crisp white sheets. Enjoy the soaking tub in the primary bath with views of the lake.
The three additional bedrooms offer plenty of room for guests: 1 Queen bed, 1 bunk bed with Full size bottom bunk and twin on top, as well as an office with a pull out Queen bed. A full guest bath with a tub/shower combo is on the second floor.
In the basement, you’ll find ping pong and air hockey tables, plus a washer/dryer.
2 direct routes from the property to the lake allow for easy access for guests. Enjoy outdoor games on the large, flat lawn and take one of the two kayaks for a ride around the lake. Dine outside with the large outdoor dining set that seats a total of 8 guests.
Cheshire is a quiet, rural community. We like to visit four nearby farms: Lakeview Orchard offers seasonal pick your own fruit and amazing cider donuts. Mountain View Farm has pick your own berries. You can buy fresh pastured eggs at Square Roots Farm, and Whitney's Farm Market has a small grocery with local produce - most notably their own tomatoes and corn.
The Ashuwillticook Rail Trail, winding 13 miles along Cheshire Lake between Pittsfield and Adams, is just down the road. For the more adventurous, an Appalachian Trail trailhead is 5 minutes away in the town of Cheshire. Winter sports are close by with Jiminy Peak a 15 minute drive away. We are also close to southern Vermont resorts, with Mt. Snow and Stratton about an hour’s drive. Or, walk right outside and sled down the hill in our backyard.
The home is close to major cultural institutions, such as the Berkshire Museum (15 minutes), Mass MoCA (20 minutes), the Clark Art Institute (30 minutes), and Tanglewood (30 minutes).
This home truly has everything you need!
Having a car will greatly enhance your ability to explore the Berkshires effectively.
⭐️ LOCATION: This beautiful lakefront property in Cheshire offers breathtaking views year-round. The expansive grounds provide plenty of privacy for a relaxing and peaceful stay.
⭐️ PETS: Dogs may be permitted with prior owner approval. No dogs under 2 years old and no multiple pets. Please contact us for approval before booking. A $100 pet fee applies if approved.
⭐️ PARKING & EV: The home features a 2-car garage. Electric cars are welcome, and a 40-amp Level 2 charger is available for guest use.
⭐️ LAKE INFORMATION: Cheshire Reservoir (Hoosac Lake) spans nearly 418 acres, making it one of the largest lakes in the Berkshires. With a maximum depth of approximately 26 feet, the lake is ideal for boating, fishing, kayaking, and lakeside lounging. Divided into three basins, it offers both active and peaceful zones. • Guests wishing to use the golf cart or kayaks must sign a waiver in advance; management will provide this prior to arrival. • There is a steep hill from the home to the lake. Swimming is available in season; weeds are present, but cleared around the dock area for safe access.
⭐️ TECH & AMENITIES: Fast cable Internet and strong cell coverage (AT&T, Verizon, T-Mobile) ensure you stay connected.
⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Cheshire
Located in Cheshire, this holiday home is in a rural area and on the waterfront. Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center reflect the area's natural beauty and area attractions include Berkshire Scenic Railway Museum and Lichtenstein Center for the Arts. Travelling with kids? Consider Berkshire Museum and Mountain Coaster.
St Mary's of the Assumption Church - 3 min drive - 2.9 km
Mount Greylock State Reservation - 7 min drive - 4.7 km
Adams Theater - 14 min drive - 12.8 km
Skyline Country Club - 15 min drive - 10.3 km
Susan B. Anthony Birthplace Museum - 17 min drive - 14.6 km
Getting around
Pittsfield Station - 12 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 24 min drive
Restaurants
Applebee's Grill + Bar - 12 min drive
Cumberland Farms - 11 min drive
Wendy's - 11 min drive
JJ's Lodge - 19 min drive
Cumberland Farms - 15 min drive
Frequently asked questions
Is Berkshires Lakefront Retreat by Evergreen Home pet-friendly?
Yes, this property allows dogs with a maximum weight of up to 23 kg per pet.
How much does it cost to stay at Berkshires Lakefront Retreat by Evergreen Home?
As of 7 May 2026, prices found for a 1-night stay for 2 adults at Berkshires Lakefront Retreat by Evergreen Home on 22 June 2026 start from AU$982, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Berkshires Lakefront Retreat by Evergreen Home?
On-site parking is available at the property.
What time is check-in at Berkshires Lakefront Retreat by Evergreen Home?
Check-in begins at 4:00 PM.
What time is check-out at Berkshires Lakefront Retreat by Evergreen Home?
Checkout is at 11:00 AM.
Where is Berkshires Lakefront Retreat by Evergreen Home located?
This family-friendly Cheshire holiday home is located on the waterfront, 1.8 mi (2.9 km) from St Mary's of the Assumption Church, and within 9 mi (15 km) of Berkshire Scenic Railway Museum and Lichtenstein Center for the Arts. Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center are also within 9 miles (15 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house was very clean when we arrived. We loved the location.
There’s a lot to do in this area! The Berkshires are beautiful this time of year. Nearby Pittsfield seems to be going through a renaissance of sorts. Also, The Berkshire Botanical Gardens is a great place to enjoy gardens. Lots of hiking!
Wonderful house with everything we could want. Absolutely loved the access to spices and condiments in the kitchen. Only reason we gave a 4 for location was because of how far we were from any restaurants/stores. Perfect location for people we plan to cook more of their meals.
Dawn A.
Stayed 2 nights in Jul 2024
Response from VrboOwner on 8 Aug 2024
Thanks for staying Dawn! For reference in terms of location, this property is a 10 minute drive to the closest two grocery stores. An 8 minute drive to Target, mini golf, driving range, and ice cream shop. And a 6-8 minute drive to the closest restaurants, gas station, spa, coffee shop, and hiking at Mt Greylock.
The house was beautiful, clean, and so well stocked with everything we needed. Our kids loved the bunk beds and kayaking around the lake. The view and property was amazing and so peaceful! Communication with the property manager with super quick and easy. The bike path is really close and nice! Quick ride to Mass Moca and other things to do. Overall wonderful trip!
Spent a weekend to join up with college friends and their families. The house was spotless on arrival and there was ample room for everyone. The air hockey table was a great attraction for the kids. The setting of the house was lovely and very convenient to skiing at Jiminy peak. Thank you for accommodating such a big party!
John B.
Stayed 2 nights in Jan 2023
Response from VrboOwner on 16 Aug 2023
Thanks so much for staying John! It was our pleasure to host you your group!
Came up to stay the weekend for freshgrass festival. The house was great and clean, updated appliances, kitchen and bathroom. The lake is very clean, but we didn't go in. We were able to watch a couple of bald eagles flying around the lake. Only concern was that the garage smelt like wet dog. Not a big deal because we didn't hang out in there but the odor was strong when you went in. Would recommend to anyone looking for somewhere to stay in the area.
The house was so clean and comfortable. The kitchen was well equipped with everything one would need for meal prep. The kids loved the bunk bed, air hockey table and ping pong table. We loved the fire place and the views!
Amy S.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 22 Feb 2026
Thanks for staying Amy!
About the host
Hosted by Evergreen Home
EVERGREEN HOME VACATION RENTALS is a locally owned and operated company with a focus on concierge vacation rental services. Our team's passion is working with people to create beautiful spaces to be enjoyed for an extended stay or just for a quick getaway. We believe in hard work, open communication and a hands on approach to business. Our team of hosts include Shana, Molly, and Ari and we are ready to help you plan and enjoy your next vacation or work trip. Thanks for checking out our listings, we'd love to invite you to stay!!
Languages:
English
Premier Host
They consistently provide great experiences for their guests