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!
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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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.
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 deadlock
About the area
Winsted
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 hiking and cycling.
Is Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air?
As of 14 April 2026, prices found for a 1-night stay for 2 adults at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air on 15 April 2026 start from NZ$383, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air?
On-site parking is available at the property.
What time is check-in at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air?
Check-in begins at 3:00 PM.
What time is check-out at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air?
Checkout is at 11:00 AM.
Where is Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air located?
This family-friendly Winchester holiday home is located on a lake, just steps away from Highland Lake and Burr Pond State Park. Platt Hill State Park is 1.2 mi (2 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
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!!
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.
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.
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
Verified
10/10 Excellent
Michelle P.
8 October 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
Response from VrboOwner on 17 March 2020
Thanks your you note Michelle. I have to say I was pretty impressed with your ambitious traveling, not to mentioned your 7-mile run around the periphery of the lake. Happy you found us to be good base for your adventures, and that you had a good time while here too. Best, Jack
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.
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
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
Archival
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
Response from VrboOwner on 17 March 2020
Thanks your nice note Lisa ! Glad you had a good time. Regarding cell phone, we use Sprint which works well, but some of the others are definitely challenged. People have had some luck with the other carriers by walking up to the top of the driveway. Next time you come...I have more paddles in the basement...I will make sure they are more visible. Good idea regarding the small row boat. I think I will find one.
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.
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!!
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.
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!!!
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.
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!
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.
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
About the host
Hosted by JohnSalvatoreHerman
Long time lake resident, long ago it won my heart. We made a lot of memories over the years here. When the time came to rebuild the cottage, we wanted to keep it true to the early 1900's cottage it had always been. It has all the modern conveniences now, but despite this, I hope you agree we maintained its authentic charm. It still feels like the cottage our family grew up in over those many golden summers, long to be remembered. We welcome others now to make special memories too.