Title: Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&selected=34004684&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air ## Photo gallery for Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air ![Exterior - Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air (Winchester)](https://images.trvl-media.com/lodging/35000000/34010000/34004700/34004684/910c0bd7.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV, fireplace, books - Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air (Winchester)](https://images.trvl-media.com/lodging/35000000/34010000/34004700/34004684/0b822177.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air (Winchester)](https://images.trvl-media.com/lodging/35000000/34010000/34004700/34004684/1bf080b1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air (Winchester)](https://images.trvl-media.com/lodging/35000000/34010000/34004700/34004684/0f4a6e1f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, books - Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air (Winchester)](https://images.trvl-media.com/lodging/35000000/34010000/34004700/34004684/e6c57ecb.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Nestled among the best locations at Highland Lake, this charming Victorian cottage offers a tranquil retreat. Enjoy canoeing, kayaking, and sailing on the lake or relax in the warm sunshine on the east side of the lake. The fully equipped kitchen features an open-concept design with original and vintage materials. ## Reviews 10 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 71300 sq ft ## Popular amenities - Kitchen - Washing machine - Dryer - Free Wi-Fi - Air-conditioning - Outdoor space ## 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. ### Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air 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! ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transport - Car required - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Full-sized refrigerator/freezer - Hob - Microwave - Oven - Spices - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room ### Entertainment - Books - Games - Smart TV with cable/satellite channels ### Outdoor areas - Dock - Garden - Gas grill - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoke-free property ### Services and conveniences - Iron/ironing board - Phone ### Location highlights - Near a hospital - On a lake ### Things to do - Kayak - Birdwatching nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Ice skating nearby - Jet skiing nearby - Mountain biking nearby - Sailing nearby - Sledding nearby - Swimming nearby - Water skiing nearby - Water tubing nearby ### 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) - Fire extinguisher - Deadbolt lock ### General - Garden - Unit size: 1,300 square feet ## Similar properties ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/5fee96a0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Courtyard by Marriott Waterbury Downtown Waterbury - Free Wi-Fi - Restaurant - Air-conditioning - Gym 8.4 Very good 1,139 reviews £76 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&selected=34227&PinnedHotelID=34227&HadPinnedHotel=true®ionId=-1&adults=2) ![Free buffet breakfast ](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG Southington - 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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 Not a location for wild parties. We live next door. Families are welcome - keg parties are not. IMPORTANT - In winter months 4-wheel or All-Wheel drive vehicles are require. 2-wheel drive vehicles will not work. ### 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 This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking. 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 deadlock 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 ### We should mention A car is required for transport to and from this property ### Property is also known as Beautiful Immaculate year round lakefront at Highland Lake ## About the area Located in Winchester, this holiday home is on a lake. Winchester Historical Society and Warner Theater are local landmarks, and some of the area's activities can be experienced at The Marina at Highland Lake and Laurel Lanes. Travelling with kids? Consider KidsPlay Museum and Action Wildlife Foundation. Discover the area's water adventures with jet skiing and waterskiing nearby, or enjoy the great outdoors with mountain biking and hiking/biking trails. [Visit our Winsted travel guide](https://www.expedia.co.uk/Winsted.dx3000430645) [View more Holiday homes in Winsted](https://www.expedia.co.uk/Winsted-Private-Holiday-Homes.d3000430645-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![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%7C41.89073%2C-73.09463&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=GKRkZJe4Lh9EQ8IUKRYiw5ztLwQ=) Winchester, CT ### What's nearby - ![Six Flags New England](https://images.trvl-media.com/place/6070305/af0e89fe-ad2f-444c-b5b3-b84cff6a3c6d.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Six Flags New England 56 min drive \- 41.1 miles - Burr Pond State Park 1 min walk \- 0.1 miles - Highland Lake 2 min walk \- 0.1 miles - PeoplesBank Arena 48 min drive \- 34.1 miles - MGM Springfield 59 min drive \- 44.6 miles ### Getting around - Hartford, CT (BDL-Bradley Intl.) 45 min drive ### Restaurants - McDonald's 9 min drive - Dunkin' 11 min drive - Subway 10 min drive - Little Red Barn Brewer 10 min drive - Dunkin' 8 min drive ## Frequently asked questions ### Is Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air pet-friendly? ### How much is parking at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air? ### What time is check-in at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air? ### What time is check-out at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air? ### Where is Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 55 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Bethanie T. 23 Sept 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Cozy Cottage “The Lone Pine” Beautiful location, spacious amenities. The soaking tub was absolutely amazing! ##### Bethanie T. Stayed 3 nights in Sep 2024 ### 10/10 Excellent #### Janine M. 11 Oct 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely lake house The house was charming and the lake views are absolutely beautiful! Enjoyed our stay! Excellent host!!! ##### Janine M. Stayed 5 nights in Oct 2024 ### 10/10 Excellent #### Colleen S. 16 Dec 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Convenient and comfy 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. ##### Colleen S. Stayed 3 nights in Dec 2024 ### 10/10 Excellent #### Claudia M. 13 Jul 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Awesome Vacation Property was immaculate. Host very accommodating. Great swimming, boating and relaxing. Looking forward to renting again next year! ##### Claudia M. Stayed 7 nights in Jul 2024 ### 10/10 Excellent #### mike m. 28 Aug 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Outstanding Stay! 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!! ##### mike m. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Roger K. 24 Jun 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Updated Antique Cottage 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. ##### Roger K. Stayed 7 nights in Jun 2024 ### 10/10 Excellent #### Carole K. 28 Apr 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful unique property 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. ##### Carole K. Stayed 3 nights in Apr 2024 ### 10/10 Excellent #### Linda H. 1 Sept 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Return to Highland Lake 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 ##### Linda H. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Elaine C. 12 Sept 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Highland Lake I’ve missed you 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. ##### Elaine C. Stayed 6 nights in Sep 2023 ### 10/10 Excellent #### Teri D. 25 Aug 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 5 Star, excellent property, location and service! 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! ##### Teri D. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Rick M. 6 Sept 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Best All excellent -- waterfront, layout, kitchen, host, feel, area! Really nice. Mattresses are on the firm side. ##### Rick M. Stayed 7 nights in Aug 2023 ### 10/10 Excellent #### tammy g. 5 Jun 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lake Getaway Clean, cute and cozy. As advertised. Only drawbacks were the weather and fish weren’t biting. ##### tammy g. Stayed 4 nights in Jun 2023 ### 10/10 Excellent #### kathy r. 4 Jul 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Love this sweet cottage Weather didn’t cooperate much, but we still had a beautiful week at the lake. When it was raining, we played games. Highly recommend. ##### kathy r. Stayed 7 nights in Jun 2023 ### 10/10 Excellent #### Michelle P. 8 Oct 2018 #### GREAT!!! This was a great place. We traveled all over the state and into Vermont. John was great. I would suggest having a list of things to do in the area as well as a detailed map of Connecticut and the surrounding states. We just couldn't orient ourselves and get the overview of the state just from our phone maps. Anyway it was great! The house is beautiful. I highly recommend this place. ##### Michelle P. Stayed 5 nights in Sep 2018 ### 10/10 Excellent #### Mary B. 17 Oct 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely Lakeside Location My husband and I spent 3 nights at this beautifully restored lakeside cottage. The house was super clean and well equipped. The weather did not cooperate so we did not spend as much time paddling on the lake as we had wished. However the lake view from the beautiful cottage windows was so pretty. We were treated to a sightseeing ride around the lake in our host John’s boat which was so thoughtful. Hoping to plan another getaway in the future to this lovely cottage. Thank you for sharing it with us! Mary and Jim ##### Mary B. Stayed 3 nights in Sep 2020 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Lisa H. 21 May 2017 #### Charming, quiet, peaceful lakefront escape off season This recently and lovingly renovated cottage on the lake was the perfect get away during the week in mid May. The cottage is beautifully designed, well appointed with intriguing historical and architectural details. The ample deck gets full sun most of the afternoon well into the evening. We rejuvinated ourselves by observing the natural beauty of the property and were kept delighted with the robins, chipmunks and other wildlife in and outside the water. The quiet exceeded our expectations (always a challenge on a lake front property). The owners live a few yards away for any questions or help as needed but were invisible during our stay. My husband is already asking when will we be returning. Only one hour from the New Haven area and just over 2 hours from Boston it is a great location for a low key vacation. Next time we hope to get out on the lake in the canoe, which will be an experience with only one kayake paddle. A small row boat would be a plus. Be aware there is no cell phone service from at least three of the most common carriers. Internet access was available and reliable. Would highly recommend a stay at this location for a couple and or a place to meet up with grown youg adult children who have moved out of state but who would enjoy sharing an affordable vacation. ##### Lisa H. Stayed 3 nights in May 2017 ### 10/10 Excellent #### cathie j., milford, pa 9 Jun 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Relaxing My sister and our two cousins rented this cottage for the week and thoroughly enjoyed it. House was very clean and lovely. Kayaking and hiking were on the to do list and was great fun. We would all highly recommend a stay here. ##### cathie j. Stayed 7 nights in May 2022 ### 10/10 Excellent #### Regina C. 8 Sept 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Looking for a lake house experience? Look no further. Great care went into the update of this home, it is full of charm and all the conveniences of home and sits on a very clean lake! Waking up to the beautiful lake views from the two front bedrooms starts your day off right! The dock provides access to the water with walk-in steps making it easy for both adults and children. We enjoyed the canoe, kayaks and the host was very gracious and gave my family a tour of the lake in his motorboat. We spent many hours on the large front deck, having coffee in the morning and diner in the evening. If you are looking for the lake experience of relaxation and plenty of water activities this is it! Thank you for a wonderful stay!! ##### Regina C. Stayed 9 nights in Aug 2021 ### 10/10 Excellent #### Terry N. 28 Aug 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Summer Vacation This is our sixth year vacationing on a lake in New England with my family. The accommodations were lovely and the lake was pristine. It was a perfect location for my grandchildren (ages 4 & 5). Both were tearful when it was time to leave. Although we spent much of our time in the water, the area had a lot to offer. The owners could not have been more accommodating. This was definitely a vacation to remember and we hope to return. ##### Terry N. Stayed 7 nights in Aug 2021 ### 10/10 Excellent #### kathy r. 25 Jul 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful experience We had a blast. Peace and quiet when we needed it. And fun in the sun when we wanted it! This lakefront property had it all! Looking forward to next year!!! ##### kathy r. Stayed 7 nights in Jul 2021 ### 10/10 Excellent #### Karen H. 26 Jun 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful lake house Excellent rental experience. Loved the property, the large deck, full kitchen and grill. The lake was clean and refreshing, we enjoyed boating and swimming each day. Friendly and helpful owners/neighbors. Would love to return. ##### Karen H. Stayed 6 nights in Jun 2021 ### 10/10 Excellent #### Linda W. 14 Jun 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lakeside idyll Lovely, peaceful, charming. Beautiful view. Very nice owners. ##### Linda W. ### 10/10 Excellent #### Janet B., Cape Cod, Massachusetts 17 May 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beauty on the lake! We so appreciated our stay! The home and deck were amazing! Everything we needed was in the home, check in was easy, great communication, clean, cozy with many nice touches! ##### Janet B. Stayed 3 nights in May 2021 ### 10/10 Excellent #### Lauren K. 26 Apr 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Relaxing weekend at the lake We had a great time relaxing at this cute lake house! It was the perfect size for me, my husband and 8 month old son and we enjoyed spending time on the deck looking at the water. We would definitely book again for a future trip especially once the little one gets older and he can enjoy the water more. ##### Lauren K. Stayed 3 nights in Apr 2021 ### 10/10 Excellent #### Vicki K. 21 Apr 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great week at the lake! We had a great time at this lake rental. Jack was very responsive and set us up to go canoeing on the lake. The house was very cozy, with beautiful views. Would love to come back in the future! ##### Vicki K. Stayed 6 nights in Apr 2021 ---