Title: Lakeside Oasis w/ Kayaks & Charm - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Lakeside Oasis w/ Kayaks & Charm Lakefront vacation home with kitchen and balcony ## Photo gallery for Lakeside Oasis w/ Kayaks & Charm ![Interior - Lakeside Oasis w/ Kayaks & Charm (Cheshire)](https://images.trvl-media.com/lodging/120000000/119460000/119451300/119451283/596834f1.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Lakeside Oasis w/ Kayaks & Charm (Cheshire)](https://images.trvl-media.com/lodging/120000000/119460000/119451300/119451283/c95504f4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Lakeside Oasis w/ Kayaks & Charm (Cheshire)](https://images.trvl-media.com/lodging/120000000/119460000/119451300/119451283/b8c67e85.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Lakeside Oasis w/ Kayaks & Charm (Cheshire)](https://images.trvl-media.com/lodging/120000000/119460000/119451300/119451283/3959fbb6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Lakeside Oasis w/ Kayaks & Charm (Cheshire)](https://images.trvl-media.com/lodging/120000000/119460000/119451300/119451283/bf807b53.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Lakeside Oasis w/ Kayaks & Charm provides amenities like a firepit and a garden. Guests can connect to free in-room WiFi. ### Entire home 2 bedrooms1 bathroom ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Outdoor Space - Parking available ## Add dates for prices Check-in Check-out Travellers ## 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! ## 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 - Boat - 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 ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119150000/119149300/119149218/03820a01.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Getaway w/ Game Room & Theatre Pittsfield - Kitchen - Washer - Dryer - Air conditioning 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&selected=119149218&PinnedHotelID=119149218&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/104000000/103900000/103890300/103890290/b1f2d951.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Crooked Lake Cabin Averill Park - Washer - Dryer - Free WiFi - Air conditioning 10 Exceptional 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&selected=103890290&PinnedHotelID=103890290&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69650000/69640700/69640625/4567d4f0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Country Living just minutes from Everything! 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Bennington - Kitchen - Pet friendly - Parking included - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&selected=93206840&PinnedHotelID=93206840&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Information provided by the property may be translated using automated translation tools ### Rules \- no smoking anywhere inside the house - no overnight guests beyond those outlined in the booking ### Pets Pets not 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 Property Registration Number c0541830580 ### Property is also known as 417729 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C42.54797%2C-73.17665&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=u2utfyuTtSmvNnsuW2vADirUNCE=) Cheshire, MA #### What's nearby - St Mary's of the Assumption Church \- 4 min drive \- 2.9 km - Mount Greylock State Reservation \- 7 min drive \- 3.9 km - Berkshire Scenic Railway Museum \- 13 min drive \- 13.2 km - Skyline Country Club \- 13 min drive \- 9.7 km - Jiminy Peak Mountain Resort \- 24 min drive \- 21.0 km #### Getting around - Pittsfield Station - 16 min drive - Pittsfield, MA (PSF-Pittsfield Municipal) - 31 min drive #### Restaurants - ‪Viking Pub - ‬10 min drive - ‪Dunkin' - ‬12 min drive - ‪Cumberland Farms - ‬16 min drive - ‪Bob's Country Kitchen - ‬9 min drive - ‪Dunkin' - ‬4 min drive ## Frequently asked questions ### Is Lakeside Oasis w/ Kayaks & Charm pet-friendly? ### How much is parking? ### What time is check-in at Lakeside Oasis w/ Kayaks & Charm? ### What time is check-out at Lakeside Oasis w/ Kayaks & Charm? ### Where is Lakeside Oasis w/ Kayaks & Charm located? ## Have a question? 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