Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Winchester, Connecticut
$297 avg/night Minimum Stay 3 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 7

Max Sleeps

Night 3 nights

Min Stay






Charming, traditional cottage design fully renovated and modernized, located among the very best of locations at Highland Lake.

If you have rented cottages before at Highland Lake, you know that location on the lake makes a big difference. Our cottage is located on the favored east side of the lake, with best sunshine. It is located away from the boat traffic and boat wake waves, on a quiet cove open to the largest of the lakes bays. VERY nice swimming area for kids and adults, with shallow comfortable area for kids and deep are for grown-ups. It has the important things experienced visitors to our lake recognize.

If you are aesthetically minded, if you are looking for something particularly charming and special, you will love this Victorian era waterfront cottage totally restored from the ground up in 2016. If you are seeking a very nice spot on the lake, you will love this property. Canoe, Kayak, Sunfish Sailboat, and more to enjoy.

It is a Victorian beauty, but fully restored in 2016 to high standards. Toasty warm in winter with lower level radiant heated floor, air conditioned for summer.

Fully equipped kitchen, open-concept. We re-purposed original and vintage materials for this loved Victorian era cottage during our restoration. Every window and door has a story. Just ask us!

Easy to use gas fireplace. Great for crisp mornings.

Bedrooms include: one queen, one full and 2 bunks. Wake up in the queen and full bedrooms to sunrise on the lake. Also upstairs, is a comfortable reading area and desk, a full bathroom with a 2 person, fully tiled shower, while the downstairs bath has a new claw foot soaking tub.

Downstairs, you will find a fully equipped kitchen, full-sized fridge, dual-fuel stove (gas stove top/electric oven), dishwasher and apron farm sink. Guests can dine on the dining table or at the kitchen peninsula. We have an open concept kitchen/dining/living room area which opens, through french doors, onto a large deck, just steps from the lake front. Enjoy the gas grill and picnic table for afternoon BBQs and sunsets for a lovely evening dinner party.

Bring your boat or jetski and tie up at our lakefront dock in front of the cottage. This lake is great for swimming, boating, water-skiing and fishing. Private lawn and water front. Sunny side of the lake. The cottage is close to the Secret Spot,' (shallow area great for small children to play in the water). We live next door to the cottage. We live next door, if you need help with anything. Our boat is parked on the south side of the dock in front of our place, your boat, if you bring one, is docked on the right north side directly in front of your cottage.

Our area offers wonderful restaurants and grocers using locally produced food, Farmer's Markets (don't miss Litchfield's Saturday Farmer's Market!), the Gilson Cinema/Cafe, Antiquing, nearby fly-fishing, hiking, and biking. Stop in at a local farm for just picked corn or tomatoes, or an after dinner ice-cream cone.

For anyone up for a Berkshires experience, we are less than a one hour, country drive from Tanglewood, Shakespeare and Co., Stockbridge, Great Barrington, Lenox, and the Outlets at Lenox.

During the summer, we request a minimum 7 day booking, Saturday to Saturday. Also, we cannot accommodate pets, due to potential allergies of renters. However, there is a highly respected kennel close to the other side of the lake.

Of course, it's great in the summer, but fall and winter offer their own special activities. Fall leaves, apple picking, hay rides and pumpkin patches in the country. Winter snow, skiing, flannel sheets and cozy fires. Our cottage can comfortably accommodate all seasons!

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1300 Sq Ft (121 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator (full Size) Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Dock Garden Gas Grill Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fitness Facilities Nearby Golf Nearby Hiking/biking Trails Nearby Jet Skiing Nearby Kayak On Site Mountain Biking Nearby Sledding Nearby Water Skiing Nearby Water Tubing Nearby
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Playground
  • LOCATION HIGHLIGHTS

    Near A Hospital On The Lake
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 7

Map Map

School District Rates & Availability

Review Review

  • Colleen S.

    Submitted Dec 16, 2024

    Stayed Dec 12, 2024

    This was our second time staying here. Although we’ve only come in the winter, we would definitely return to enjoy the lake in the summer. Always a comfortable, easy stay.

  • Janine M.

    Submitted Oct 11, 2024

    Stayed Oct 6, 2024

    The house was charming and the lake views are absolutely beautiful! Enjoyed our stay! Excellent host!!!

  • Bethanie T.

    Submitted Sep 23, 2024

    Stayed Sep 19, 2024

    Beautiful location, spacious amenities. The soaking tub was absolutely amazing!

  • Linda H.

    Submitted Sep 1, 2024

    Stayed Aug 24, 2024

    My husband and I owned a home on Highland Lake and had to unfortunately sell it but I’ve always wanted to go back. This lakeside home is well kept and comfortable. The Nextdoor owner couldn’t be nicer and offered his help at any time. His explanation of every detail of this home was very accurate

  • mike m.

    Submitted Aug 28, 2024

    Stayed Aug 10, 2024

    Our week at Jack's lakehouse was really great. Jack took us out on his boat, and we had a great time swimming off the dock. The house was perfectly clean and had everything you would need to do some cooking/grilling. Nice big deck. Cant wait to go back!!

  • Teri D.

    Submitted Aug 25, 2024

    Stayed Aug 17, 2024

    This was our second year renting this gorgeous, lovingly restored lakeside cottage. We love the attention to detail in the restoration including leaded windows and stunning wood floors plus a wonderful claw foot tub. The lakeside location could not be more perfect with stunning views from the sitting room, bedrooms and deck. Swimming, fishing and kayaking were just a few of our activities. To top it off, the owner is there at your beck and call. We asked for a fire pit and we had one in a few hours. Dishwasher broke down, we had a new one the same day. John even gave my grandsons a boat ride and let the 10 year old drive the boat! We just love this place so much! It’s the best! Thank you John!

  • Claudia M.

    Submitted Jul 13, 2024

    Stayed Jul 6, 2024

    Property was immaculate. Host very accommodating. Great swimming, boating and relaxing. Looking forward to renting again next year!

  • Roger K.

    Submitted Jun 24, 2024

    Stayed Jun 15, 2024

    My family enjoyed a week at the cottage on Highland Lake. The cottage was very clean and well appointed. Situated on the eastern shore provides evening sunsets. Jack lives next door and was very helpful. We plan on returning.

  • Carole K.

    Submitted Apr 28, 2024

    Stayed Apr 25, 2024

    We absolutely loved our getaway at John's place. So many unique touches to the lakefront cabin and we loved the overall retro style of the place. Brought me back to simpler times. The beds were comfy and the place offered space for all. We enjoyed our nights sitting in front of the fire pit looking out at the lake. Host was extremely friendly and receptive. Highly recommend.

  • Elaine C.

    Submitted Sep 12, 2023

    Stayed Sep 5, 2023

    This property could not have been better. It was clean as could be and set up to be very comfortable. The kitchen is complete for all your cooking needs. The views of the lake were stunning. We have stayed in VRBOs in the States and Europe and of all of them John is the best host so far. He saw to our every need without hesitation and then some. He is a cool dude. We will stay here again! Thank you John, you rock.

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Total

Includes taxes and fees
$297+
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