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Lakeside Oasis w/ Kayaks & Charm

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Multiple kayaks available for guest use, offering adventure right from the shoreline.
A serene trail cutting through vibrant woods perfect for walking or cycling in fall.
Fully equipped kitchen with stainless steel appliances, including refrigerator, oven, microwave, and dishwasher.
A sweeping autumn vista from the summit of Mount Greylock, showcasing rolling hills painted in fiery fall hues reds, oranges, and golds stretching into the distance.
Bright and spacious living room with a cozy stone fireplace as the centerpiece.
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace
  • Kitchen
  • Barbecue grill

Explore the area

View in a map
Cheshire, MA
  • Jiminy Peak Mountain Resort
  • Mount Greylock State Reservation Visitor Center
    ‪18 min drive‬
  • Mount Greylock
    ‪45 min drive‬
  • Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪28 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

1 bathroom

Bathroom 1

Spaces

Kitchen
Balcony
Garden
Dining area

About this property

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!

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Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Outdoor space
Parking available

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number c0541830580

About the area

Cheshire

Located in Cheshire, this holiday home is on the waterfront. Adams Theater and Susan B. Anthony Birthplace Museum are cultural highlights, and some of the area's landmarks include East Hoosac Quaker Meetinghouse and Crane Museum of Papermaking. Berkshire Scenic Railway Museum and Berkshire Museum are also worth visiting.
Map
Cheshire, MA

What's nearby

  • Mount Greylock State Reservation - 10 min drive - 5.7 km
  • Mount Greylock State Reservation Visitor Center - 18 min drive - 13.1 km
  • Massachusetts Museum of Contemporary Art - 25 min drive - 25.6 km
  • Williams College - 36 min drive - 36.8 km
  • Mount Greylock - 45 min drive - 36.6 km

Getting around

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

Restaurants

  • ‪Wendy's - ‬12 min drive
  • ‪Applebee's Grill + Bar - ‬13 min drive
  • ‪Cumberland Farms - ‬12 min drive
  • ‪Cumberland Farms - ‬16 min drive
  • ‪Dunkin' - ‬12 min drive

Frequently asked questions

Is Lakeside Oasis w/ Kayaks & Charm pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Lakeside Oasis w/ Kayaks & Charm?

Check-in begins at 3:00 PM.

What time is check-out at Lakeside Oasis w/ Kayaks & Charm?

Checkout is at 11:00 AM.

Where is Lakeside Oasis w/ Kayaks & Charm located?

Situated on the waterfront, this holiday home is 2 mi (3.2 km) from St Mary's of the Assumption Church and within 9 miles (15 km) of Mount Greylock State Reservation and Adams Theater. Berkshire Scenic Railway Museum and Mount Greylock State Reservation Visitor Center are also within 9 miles (15 km).

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