Entire home
Lakeside Oasis w/ Kayaks & Charm
2.0 star property
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Entire home
2 bedrooms1 bathroom
Popular amenities
- Dryer
- Washer
- Parking available
- Fireplace
- Kitchen
- Barbecue grill
Explore the area

Cheshire, MA
- Jiminy Peak Mountain Resort
- Mount Greylock State Reservation Visitor Center18 min drive
- Mount Greylock45 min drive
- Pittsfield, MA (PSF-Pittsfield Municipal)28 min drive
Room options
About the neighborhood
Cheshire
On lake.You'll be within 3 miles (5 km) of St Mary's of the Assumption Church and 6 miles (10 km) of Mount Greylock State Reservation with a stay here. Also within 9 miles (15 km) are Adams Theater and Berkshire Scenic Railway Museum.
What's nearby
- Mount Greylock State Reservation - 10 min drive - 3.6 miles
- Mount Greylock State Reservation Visitor Center - 18 min drive - 8.2 miles
- Massachusetts Museum of Contemporary Art - 25 min drive - 15.9 miles
- Williams College - 36 min drive - 22.9 miles
- Mount Greylock - 45 min drive - 22.8 miles
Getting around
- Pittsfield Station - 16 min drive
- Pittsfield, MA (PSF-Pittsfield Municipal) - 31 min drive
Restaurants
- McDonald's - 11 min drive
- McDonald's
- Wendy's - 12 min drive
- Applebee's Grill + Bar - 13 min drive
- Starbucks - 13 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.
Lakeside Oasis w/ Kayaks & Charm
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!
Things you'll love!
- Four kayaks and a pedal boat!
- Fire pit and Adirondack chairs!
- Waterfront access to Cheshire Lake!
- Fully stocked with all the necessary kitchen and bathroom amenities to make your stay feel like home!
Kitchen
As you enter the home, the first space that catches your attention is the beautifully redesigned kitchen. Fully renovated, it features stunning stone countertops, a dishwasher, and a gas stove, all equipped with essentials for cooking up a stellar meal with family and friends. A charming breakfast bar offers a perfect spot for quick bites before heading out for the day's adventures.
Dining & Living Area
Flowing seamlessly from the kitchen, the main dining and living space is designed for comfort and entertainment. The dining room has seating for up to six, complemented by a new overhead fan that circulates a refreshing lake breeze. The living room offers cozy seating for six, including a fully reclining sofa, a smart television, and a selection of games for fun-filled evenings. A new gas fireplace adds warmth and ambiance during cooler months.
Bathroom & Laundry
The full bathroom features a brand-new tiled shower with a double shower head and all the essentials for a quick freshen-up. No need to bring soap or towels — the bathroom is fully stocked for your convenience. Next to the bathroom is a laundry closet, equipped with detergent for a quick wash if needed.
Bedrooms
Both bedrooms are cozy spaces, set up with fresh linens, duvets, and ceiling fans for comfort. Each room includes a smart television, perfect for late-night movies in bed. Plenty of storage space is available in the dressers, allowing you to unpack and settle in comfortably.
Outdoor Space & Backyard
The backyard truly shines as the crown jewel of the home. Off the back deck, you’ll find a new electric grill ready for outdoor cooking. The yard is stocked with four kayaks, a pedal boat, and a charming fire pit with Adirondack chairs—ideal for s'mores and stories after a day on the lake. This outdoor haven is perfect for relaxing, dining, or enjoying the breathtaking lakeside surroundings.
Guests have access to the entire home, as well as private lake access right outside the back door.
Please message us through the booking application during your stay.
Cheshire Lake in the Berkshires is a serene, scenic spot perfect for boating, fishing, and swimming amid stunning mountain views. Surrounded by lush forests and charming small towns, the area offers outdoor adventures such as skiing at Jiminy Peak, cultural attractions like Mass Moca and Tanglewood less than a half hour away, and excellent dining at everyone's favorite tavern The Olde Forge. Whether relaxing lakeside or exploring the nearby trails, Cheshire Lake provides a peaceful retreat in the heart of the Berkshires.
The home is situated in Willow Cove, a charming little hamlet built into a cove on Cheshire Lake. Like many lakeside communities, the roads are narrow and parking is tight but with some finesse you'll have no problem getting two cars parked in the spot out front of the house. One thing to note is to keep your speed down in the cove as there's always people out walking their dogs and the neighborhood kids strolling to and from the lake. All that said, important to note that your lake access is private and is specific to the house and not shared with others.
- no smoking anywhere inside the house
- no overnight guests beyond those outlined in the booking
- if you're going to have some friends over for a birthday party type event etc, just let us know ahead of time please!
Things you'll love!
- Four kayaks and a pedal boat!
- Fire pit and Adirondack chairs!
- Waterfront access to Cheshire Lake!
- Fully stocked with all the necessary kitchen and bathroom amenities to make your stay feel like home!
Kitchen
As you enter the home, the first space that catches your attention is the beautifully redesigned kitchen. Fully renovated, it features stunning stone countertops, a dishwasher, and a gas stove, all equipped with essentials for cooking up a stellar meal with family and friends. A charming breakfast bar offers a perfect spot for quick bites before heading out for the day's adventures.
Dining & Living Area
Flowing seamlessly from the kitchen, the main dining and living space is designed for comfort and entertainment. The dining room has seating for up to six, complemented by a new overhead fan that circulates a refreshing lake breeze. The living room offers cozy seating for six, including a fully reclining sofa, a smart television, and a selection of games for fun-filled evenings. A new gas fireplace adds warmth and ambiance during cooler months.
Bathroom & Laundry
The full bathroom features a brand-new tiled shower with a double shower head and all the essentials for a quick freshen-up. No need to bring soap or towels — the bathroom is fully stocked for your convenience. Next to the bathroom is a laundry closet, equipped with detergent for a quick wash if needed.
Bedrooms
Both bedrooms are cozy spaces, set up with fresh linens, duvets, and ceiling fans for comfort. Each room includes a smart television, perfect for late-night movies in bed. Plenty of storage space is available in the dressers, allowing you to unpack and settle in comfortably.
Outdoor Space & Backyard
The backyard truly shines as the crown jewel of the home. Off the back deck, you’ll find a new electric grill ready for outdoor cooking. The yard is stocked with four kayaks, a pedal boat, and a charming fire pit with Adirondack chairs—ideal for s'mores and stories after a day on the lake. This outdoor haven is perfect for relaxing, dining, or enjoying the breathtaking lakeside surroundings.
Guests have access to the entire home, as well as private lake access right outside the back door.
Please message us through the booking application during your stay.
Cheshire Lake in the Berkshires is a serene, scenic spot perfect for boating, fishing, and swimming amid stunning mountain views. Surrounded by lush forests and charming small towns, the area offers outdoor adventures such as skiing at Jiminy Peak, cultural attractions like Mass Moca and Tanglewood less than a half hour away, and excellent dining at everyone's favorite tavern The Olde Forge. Whether relaxing lakeside or exploring the nearby trails, Cheshire Lake provides a peaceful retreat in the heart of the Berkshires.
The home is situated in Willow Cove, a charming little hamlet built into a cove on Cheshire Lake. Like many lakeside communities, the roads are narrow and parking is tight but with some finesse you'll have no problem getting two cars parked in the spot out front of the house. One thing to note is to keep your speed down in the cove as there's always people out walking their dogs and the neighborhood kids strolling to and from the lake. All that said, important to note that your lake access is private and is specific to the house and not shared with others.
- no smoking anywhere inside the house
- no overnight guests beyond those outlined in the booking
- if you're going to have some friends over for a birthday party type event etc, just let us know ahead of time please!
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Property amenities
Internet
- Available in the house: Free WiFi
Parking and transportation
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- 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)
- First aid kit
- 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
Pets
- No pets 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 and a first aid kit
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property Registration Number c0541830580
Property is also known as
417729
Frequently asked questions
How close is Lakeside Oasis w/ Kayaks & Charm to the airport?
This vacation home is 13.9 mi (31-min drive) away from the Pittsfield, MA (PSF-Pittsfield Municipal) airport, the closest popular airport to the property.
Does Lakeside Oasis w/ Kayaks & Charm have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is Lakeside Oasis w/ Kayaks & Charm to the beach?
This vacation home is 12.8 mi (27-min drive) from Campers Beach.
Does Lakeside Oasis w/ Kayaks & Charm offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Lakeside Oasis w/ Kayaks & Charm?
No, there is no casino at this vacation home.
What time is check-in at Lakeside Oasis w/ Kayaks & Charm?
Check-in begins at 3:00 PM.
Is there free parking at Lakeside Oasis w/ Kayaks & Charm?
Free parking is not available at this vacation home.
Does Lakeside Oasis w/ Kayaks & Charm have a pool?
This vacation home does not have a pool.
Does Lakeside Oasis w/ Kayaks & Charm have a spa?
There are no spa services available at this vacation home.
How close is Lakeside Oasis w/ Kayaks & Charm to downtown Cheshire?
This vacation home is 1.2 mi away from Cheshire.
Lakeside Oasis w/ Kayaks & Charm Reviews
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