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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076

Very special, 2016 restoration, Immaculate Highland Lake direct-waterfront

Bedrooms 3
Space 1,300 sq ft
Property type house
Minimum Stay 2 - 7 nights


About the property

Wonderful family vacation house. Nice swimming area, large deck, dockage

RATE NOTE: Email for special rates on off-season visits for more that 3 days.

If you are aesthetically minded, if you are looking for something particularly charming and special, you will love this cottage. If you are seeking a very nice spot on the lake, you will love this property. Canoe, Kayak, Sunfish Sailboat, and more to enjoy.

If you have rented cottages before, you know that location on the lake makes a 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. Nice swimming area for kids. Its has the important things experienced visitors recognize.

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 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. Spectacular views. Also upstairs, is a comfortable reading area and desk, a full bathroom with a 2 person, fully tiled shower, while the downstairs bath boasts a sparkling, 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 old world dining table and Hitchcock chairs made locally, 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 or glowing white lights and sunsets for a lovely evening dinner party.

Bring your boat or jetski and tie up at our lakefront dock. 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. 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!

More Details

Member since: 2016
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english, spanish
Response time:
Within a day
Response rate:
Calendar last updated:
September 21, 2018


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. purchased this house in 1971

Why chose Winchester

Great property and location on the lake.


Winchester House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1300 sq ft
House Rules:
  • Check-in: 3:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 7
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • pets not allowed
  • non smoking only
Location Type:
  • Lakefront ...
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove ...
  • Toaster
  • Dining Area
  • seating for 7 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • Bathroom on the bedroom level has a shower. Bathroom on the lower level has a soaking tub.
  • 3 Bedrooms, Sleeps 7
  • Books
  • Games
  • Satellite / Cable
  • Television ...
  • Deck / Patio ...
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Grill ...
  • Long-term Renters Welcome
  • autumn foliage
Leisure Activities:
  • antiquing
  • bird watching
  • photography
  • scenic drives
  • sledding
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • ice skating
  • jet skiing
  • mountain biking
  • sailing
  • swimming
  • water skiing
  • water tubing


Wonderful! 4.9/5 -
(16 traveler reviews)

93% Complete
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Very special, 2016 restoration, Immaculate Highland Lake direct-waterfront
average rating of 4.9375 based on 16 reviews

Great Lakehouse!

  • 5 of 5

The Lone Pine Cottage is a wonderful house right on the lake. The Victorian had been restored with attention to detail. It was very clean and quite comfortable. The house had a lot of character with all the unique windows, clawfoot tub, very cool stove and rustic stone wall by the stairway. While the galley-style kitchen was a little tight when their were multiple cooks, it was well-equipped and we made many delicious meals. The deck was a great outdoor "room" with plenty of seating and a nice view of the sunset and at night the rail had little lights on a timer. The tree growing up through the deck was impressive. We also enjoyed gazing at the stars over the lake while sitting on the dock. We had lots of fun exploring the lake with the canoe and kayaks. The water was clear and we had fun swimming and floating right from the dock. Jack was kind and very helpful with whatever was needed, but not at all intrusive. He was a wonderful host. We visited two area wineries, Sunset Meadow Vineyards and Haight-Brown Vineyard which made for rainy day fun. We enjoyed hiking in the People's State Forest in Barkhamsted. We liked our Italian dinner at the Venetian Restaurant on Main Street in Torrington, especially the tableside Caesar salad. We spent most of our time relaxing in this cozy cottage on Highland Lake.

  • Submitted: Aug 29, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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Wonderful lake getaway

  • 5 of 5

We had a terrific week on HIghland Lake. The house is lovely, just right for our family (including our 5 and 7 year old daughters). Quaint and charming bedrooms, updated and clean bathrooms, and small but great kitchen. The deck is outstanding, like an additional room outdoors! The lake is perfect, great time canoeing and kayaking. Fun swimming off of the dock for hours a day. The Owner was so nice, very available, but not at all intrusive. All in all, an excellent place to visit, we highly recommend it!!

  • Submitted: Jul 26, 2018
  • Stayed: July 2018
  • Source: HomeAway
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Great location, cottage, and owner!

  • 5 of 5

John was great! We were quite a bit late on our first night, and he offered to let us stay an extra on the back end. Unfortunately we weren't able to take advantage of his incredible hospitality, as we had flights out to catch, but it was extremely generous of him.

Additionally, the accommodations were tremendous. The cottage was incredible, and so charming. There was a bottle of wine and some snacks, from John, on the counter when we got there and the fireplace was already warming the house. The deck was incredible, and the view was so calming and peaceful. We grilled out both nights, and had an amazing time. The beds were so comfortable, and we will hopefully be coming back again.

  • Submitted: May 22, 2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
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Idilic lake front setting with Kayaks

  • 5 of 5

This was the most relaxing vacation we have had in years. Stunning setting. Very confortable and pretty, renovated cottage. Cottage was immaculate, well equipped and well located.

The owners could not have been kinder, providing enough goodies to get us started on the day we arrived ( lovely touch). John graciously allowed us use of his boats on the lake and we enjoyed kayaking and having mini picnics with our 6 year old who just loved playing on the water - he woke up singing and went to bed singing. The perfect family vacation.

Stunning part of CT and although in the country was only a 5 min drive into town - best of both worlds.

Will be back! Thanks John for a vacation we will always remember with much fondness! Thanks for your time that you gave to us too.

  • Submitted: Oct 16, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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We had a fantastic early fall visit on our favorite New England lake!

  • 5 of 5

This was our first time staying here and it was perfect for my mom, sister and I and our two young daughters. The place is amazingly renovated with such attention to detail. The deck was beautiful and is cut around the trunk of a large maple tree. We used the propane grill on the deck one day and ate lunch at the picnic table for a memorable family meal. The kitchen was perfect and we also made use of the gas fireplace. Internet and TV setup were great with no issues. No cell reception though, which we expected and was fine. WiFi was sufficient for communicating with most people. There is no insulation between the first and second floors (which I thought was fine since you get to see the beautiful wood of the floor on the bottom as well as the top), but this could be a problem for light sleepers tying to sleep late with others up and about making noise. I love the lake off-season and hope to brave it during winter someday! Long live Highland Lake! Jack was a great host and fit in a last minute boat ride for us - which was magical and joyous. The first motor boat ride for our little girls! Thank you for a great stay, Jack!

  • Submitted: Oct 8, 2017
  • Stayed: September 2017
  • Source: HomeAway
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Bristol, CT, USA

Fisherman's Dream!

  • 5 of 5

My husband and I stayed from Sept. 17 to Sept. 23. Had a nice relaxing time enjoying the peacefulness of Highland Lake in the fall. Enjoyed fishing whenever we wanted. Lake house was very close to all the stores you might need to go to. Can't SAY enough about the OWNER--John was very helpful (above and beyond). Definitely would stay here again!

  • Submitted: Sep 23, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
35 Miles
Nearest Ferry
60 Miles
Nearest Train
25 Miles
Car: necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $100
Refundable Damage Deposit $200

In off-peak months (September through May), feel welcome to inquire about short term lease. The home is state of the art, an ideal executive rental for a period of months, in a remarkable setting, great year round. In Summer months, rental week runs from Saturday to Saturday.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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