Title: Family House On Highland Lake with Dock - 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 # Family House On Highland Lake with Dock Beachfront vacation home with kitchen and balcony ## Photo gallery for Family House On Highland Lake with Dock ![Fridge, microwave, oven, stovetop - Family House On Highland Lake with Dock (Winsted)](https://images.trvl-media.com/lodging/80000000/79740000/79739200/79739136/60333e10.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Terrace/patio - Family House On Highland Lake with Dock (Winsted)](https://images.trvl-media.com/lodging/80000000/79740000/79739200/79739136/82221594.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Family House On Highland Lake with Dock (Winsted)](https://images.trvl-media.com/lodging/80000000/79740000/79739200/79739136/0636ddb1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Family House On Highland Lake with Dock (Winsted)](https://images.trvl-media.com/lodging/80000000/79740000/79739200/79739136/17424342.jpg?impolicy=resizecrop&rw=297&ra=fit) ![5 bedrooms, in-room safe, iron/ironing board, free WiFi - Family House On Highland Lake with Dock (Winsted)](https://images.trvl-media.com/lodging/80000000/79740000/79739200/79739136/43b67f3f.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Set on a full acre with beautiful views of Highland Lake, this family estate offers the perfect retreat. Enjoy lake activities or unwind on the private dock/waterfront deck, screened-in porches, or rear deck with fire pit. The spacious dining room and chef's kitchen provide ample space for culinary adventures. ## Reviews 10 Exceptional ### Entire home 5 bedrooms4 bathroomsSleeps 122000 sq ft ## Popular amenities - Kitchen - Washer - Dryer - 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. ### Family House On Highland Lake with Dock This family estate is set privately on a full acre with beautiful views of Highland Lake. Red Barn Brewing and main street Winsted is .7 miles away. The estate is crowned with a dock/waterfront deck to enjoy the lake from. This place has something for everyone! Key Features \-Use of private dock/waterfront deck across the street from house. \-5 bed/4 bath \-Flat backyard \-Newly Renovated \-2 screened in front porches, rear deck and fire pit. \-2,000+ square feet of indoor living space Highland Lake is Connecticut's premiere lake for all kinds of recreation. Hosting Bass fishing competitions, water skiing, swimming, boating and ice fishing in the winter. Or just unwind and take in the beauty on the waterfront deck. The Master is complete with a King sized bed, en-suite and sliding door leading out to a screened-in porch with lake views where you can enjoy your morning coffee or evening wine. The upstairs also contains laundry facilities, another full bath, a Queen bedroom and two more bedrooms both with two twin beds. The downstairs living room is winged with sliding doors on both ends. The front leading out to a screened-in porch with lake views and the rear to the deck. There are three couches with room for the whole family and a Large Smart TV mounted above the fireplace for all your viewing needs. There is a spacious dining room and breakfast nook in addition to the chef's kitchen equipped for all of your culinary needs with a brand new Oven/Range and Dishwasher. There is a bedroom off of the kitchen with its own full bath and workspace. The downstairs is completed with a chic half bath. The deck off of the rear of the house has a grill, table and chairs and leads down to the patio/fire pit area and the large flat backyard. \-Public Boat launch is just minutes away. \-Parking for several cars \-Parties, events and large gatherings are not allowed. \-No pets \-No smoking ## Property amenities ### Beach - On the beach ### Ski - Close to skiing - Snowboarding nearby ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Microwave - Oven - Paper towels - Refrigerator - Stovetop ### Dining - Dining table ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 3.5 bathrooms - Bathtub - Bathtub or shower - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room - Separate dining area ### Entertainment - Smart TV ### Outdoor areas - Balcony - Barbecue grill - Firepit - Garden - Outdoor furniture ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board - Safe ### Location highlights - Near a hospital - Near the marina - On a lake - On the waterfront ### Things to do - Birdwatching nearby - Cycling nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Sailing nearby - Swimming nearby - Water skiing nearby - Water tubing nearby - Wildlife walks nearby - Winery tours 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 ### General - Garden - Unit size: 2,000 square feet ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104240000/104239000/104238981/4888311a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Modern Goshen House w/ Deck, Backyard & Views Goshen - Kitchen - Washer - Dryer - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-05&endDate=2026-01-06&selected=104238981&PinnedHotelID=104238981&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90360000/90355100/90355015/c7d2e895.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront oasis in heart of Berkshires Sandisfield - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 20 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-05&endDate=2026-01-06&selected=90355015&PinnedHotelID=90355015&HadPinnedHotel=true®ionId=-1&adults=2) ![Bar (on property)](https://images.trvl-media.com/lodging/109000000/108560000/108550200/108550147/ab3acf5f_edited_b8da.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oak Manor, a luxurious property on 6,6 acres. 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=41.92481,-73.08933&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:ci%7C%7EFhgb%7DL%3FS%3FU%3FS%40U%3FS%40U%40U%40S%40SBU%40S%40UBSBSBSBSBUDSBSDSDQBSDSDQFSDSFQDSFQFQFQFQFQHQFOHQFQHOHOHOHQHMHOJMHOJOHMLMHMJMJKLMJKJMJKLKJILKLKLIJKLGLILILILENILGLGLENGLENELENELENENCLCNCNANCLANCNANAN%3FN%3FLAN%3FN%3FN%40N%3FL%3FN%40N%40NBN%40LBN%40NBNBLBNDNDLDNDLDNDLFLDLFNFLHLDLHLHLHLFLJLHJJLJLJJHLJJLJJJLJJJLJNJJJLHNJNHLHNHLJPHNHNFNHPFPHNFPFPFPHPDPFPFRDPFRDRDPDRDRBPDRDRBRBTBRBRBRBRBT%40R%40T%40RBR%3FT%40T%40R%3FT%40R%3FT%3FR%3FT%3FTAP%3FTATAT%3FRCRATARARCTCRCTCRCRCRCRERERCREREPERERGPEPGRGPEPIPGRGNGPIPGNIPGPILIPKNINILINKLINKLKLKLKLKJKLKJKLMJKJMJMJKHMJMHMHMHMFMHMFMFOFMFMFMFODMDODMDOBODMBOBOBOBM%40OBO%40O%40O%40M%40O%3FO%3FO%3FO%3FM%3FO%3FOAOAOAOAMCOAOCOCMCOCOEMCOEMEOEMEOGMGMGMGOGMGMIMGMIMIKIMKMIMKKKMKKKKMKKMMKKKMIKMOIMKOIMKOIMIOIOIQIMIQGQIOGQIQGOGSGQGQGQEQGSEQGSESEQCSESESCSESCSCSCSCUCSAUASCSAUASASAU%3FUAU%3FQ%3FU%3FU&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=FdzYdxrhKAxxDKdS6jgxBh2pWVc=) Winsted, CT #### What's nearby - Highland Lake \- 2 min walk \- 0.2 km - The Marina at Highland Lake \- 13 min walk \- 1.1 km - Winchester Historical Society \- 19 min walk \- 1.7 km - Laurel Lanes \- 3 min drive \- 2.5 km - Walker Field \- 3 min drive \- 2.5 km #### Getting around - Bradley Intl. Airport (BDL) - 50 min drive #### Restaurants - ‪Dunkin' - ‬4 min drive - ‪McDonald's - ‬6 min drive - ‪Little Red Barn Brewer - ‬19 min walk - ‪Dunkin' - ‬6 min drive - ‪Subway - ‬8 min drive ## Frequently asked questions ### Is Family House On Highland Lake with Dock pet-friendly? ### How much is parking? ### What time is check-in at Family House On Highland Lake with Dock? ### What time is check-out at Family House On Highland Lake with Dock? ### Where is Family House On Highland Lake with Dock located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Family House On Highland Lake with Dock 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.ca/lp/b/content-guidelines) 10 - Excellent 26 8 - Good 2 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 9.6 Cleanliness ### 9.6 Location ### 10 Eco-friendliness ### 10 Property conditions & facilities ## Reviews ### 10/10 Excellent #### TJ M. Jul 8, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great place Great house for access to Highland lake. Stayed w/ another family and layout was good for multiple people. Owner very responsive. Would stay again. ##### TJ M. Stayed 7 nights in Jun 2025 ### 10/10 Excellent #### Jason B. Jan 27, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Incredible place Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. ##### Jason B. Stayed 3 nights in Jan 2025 ### 10/10 Excellent #### Karen A., North Branford Mar 10, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Work trip Great location and great accommodations! ##### Karen A. Stayed 2 nights in Feb 2024 ### 10/10 Excellent #### Patricia C. Aug 14, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Location We really enjoyed our stay. Property was close to the lake where we enjoyed 2 days of renting a pontoon. We enjoyed the very large house and property. ##### Patricia C. Stayed 4 nights in Aug 2023 ### 10/10 Excellent #### jeff c. Jul 9, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Retirement getaway Great time on the lake. Perfect house suited our needs, especially the dock on the lake and the firepit out back! Everyone had a good time. Thanks Recommend this home for a great place to get away and chill! ##### jeff c. Stayed 3 nights in Jun 2024 ### 10/10 Excellent #### Scott B. Sep 3, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Weekend Stay Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. ##### Scott B. Stayed 4 nights in Aug 2024 ### 10/10 Excellent #### Jeffrey Apr 15, 2024 Liked: Cleanliness, amenities, property conditions & facilities, communication The property was perfect for our needs. Instructions for everything was provided fabulous rental. ##### Jeffrey Stayed 2 nights in Apr 2024 ### 10/10 Excellent #### Kathy G. Jul 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect! Perfect place for our families (8 people)! Easy access to lake, watchable wildlife, quiet neighborhood (except for screaming foxes-who knew??) Very comfortable, well-laid out house-screened porches were a big hit! ##### Kathy G. Stayed 7 nights in Jun 2024 ### 10/10 Excellent #### brett c. May 22, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stey Amazing view. Great price. Great communication. ##### brett c. Stayed 4 nights in May 2024 ### 10/10 Excellent #### Caitlin L. May 27, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing Long Weekend Get Away The house was perfect for accommodating a large group of friends for a nice, relaxing break froze reality! It gave us space for cooking meals, playing games, and lounge around. The lake was perfect for a refreshing dip! It was overall an amazing experience! ##### Caitlin L. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Verified traveller Aug 27, 2023 Disliked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely home We had a wonderful vacation. The home was very clean, spacious and accommodating for our large family. It was great being able to dock our boat and we spent many hours on the lake cruising, skiing and pulling our grandchildren on a towable for their first time. They loved it! ##### Verified traveller Stayed 7 nights in Aug 2023 ### 10/10 Excellent #### Jackie O. Jul 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Bustling Lake Life The property was excellent! Ben (property owner) was incredibly responsive if we had any questions! House was spotless! Peekaboo view of the lake as there's actually another home in front of the rental. Open, clean, and comfortable! Great outdoor spaces (multi-level deck and patio with fire pit, BYO wood) to relax in a peaceful wooded setting. Kids and adults really enjoyed the lake. Small beach and swimming area about 5minute walk from the house. Great little dock for fishing/boating right at the bottom of the hill/driveway. We brought a small boat and the kids LOVED tubing around the lake. Saturday was BUSY on the lake, lots of jet-skis and boats/tubing going on. 5-10 minute drive to CVS/Stop and Shop for all your needs. Great spot for three families from MA, NY and NJ to meet up for a weekend together! ##### Jackie O. Stayed 3 nights in Jul 2024 ### 8/10 Good #### Wendy B. Sep 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Ben was an excellent communicator as we got off to a slightly rough start ( dirty patio, few hangers) and garbage at bottom of long hill to drag up. Ben he addressed each quickly. We cleaned up patio and brought up garbage cans, Ben brought some more hangers next day. It is not auto checkin- you have to contact him directly to get the entry info so an extra step. His directions were clear and we found it easily. The house is a little worn, dishwasher was not attached so fell out of hole when you opened it. We fixed that with a couple screws. No mixing or salad bowl, we served salad and mixed a cake in the pots and pans. No screen on the upper bedroom window made it hard to leave open at night. The carbon monoxide detector was unplugged on the mantle. The porches were lovely and we spent a lot of time on them. The dock is a plus and we used a local outfit to deliver a boat and water skis. (Ian and CT Watersports) The beds and bedding were clean and comfortable. If the house is full, you will probably need extra TP so be prepared. The washing machine makes a racket so dont start just before going to bed. I am sure it will be fixed by the time the next guest comes Overall, we had a lovely time as friends celebrating a birthday which is why we were there. ![Kitchen](https://a.travel-assets.com/ugc/hotel-reviews/d8178a2b-faa9-46d4-9a5a-2a7f8cc09023-1757626051746.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![Dining area](https://a.travel-assets.com/ugc/hotel-reviews/80932453-7e66-4c01-8d8f-1dd837619c71-1757626051218.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![Boating](https://a.travel-assets.com/ugc/hotel-reviews/2ce3ed3e-8f80-4625-988c-a38d6a132610-1757626050115.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Wendy B. Stayed 7 nights in Aug 2025 ### 10/10 Excellent #### Sasha A. Aug 23, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great place Very nice place and very nice owner. Will stay again next time we're in the area! Thanks so much ##### Sasha A. Stayed 2 nights in Aug 2023 ### 10/10 Excellent #### Lorraine A., College Point, NY Jan 3, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful Host The house was spacious, beautiful, and extremely clean. The host was so nice and answered messages promptly. We enjoyed playing games in the dining room and gathering in the comfortable living room around a fire. The kitchen was a great space to prepare meals for our group. We also enjoyed sitting on the back deck and around the backyard fire pit. The view of the lake from the house is spectacular. We had a wonderful weekend! ##### Lorraine A. Stayed 3 nights in Dec 2022 ### 10/10 Excellent #### Kimberly S. Jul 13, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Dream Lake Vacation! We had an amazing stay at Ben’s lake house! The house is spotless! So meticulously clean! We spent many hours lounging on the deck and dock of the lake. We brought our own kayaks, so much fun paddling in the lake. The lake is so clean! We went into town one evening to play mini golf and drive go carts. Lake Compounce is less than an hour drive. We rented a pontoon boat for a day. Just so relaxing! Ben was super responsive to all our requests!! ##### Kimberly S. Stayed 7 nights in Jul 2023 ### 8/10 Good #### Fabius F., NYC Jul 30, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Large house overlooking a lake The house is large and well equipped. The host (Ben) was very responsive. The area is pleasant, although it is not as up scale as some of the other towns in Litchfield County. The local beach was disappointing. There are nice areas to swim that require a 25 to 35 minute drive. The listing makes it look like the house is actually on the lake, but it is on a hill up a moderately steep driveway. The good part was that it is not on the road, so it was quieter than it would have been if it was actually on the lake. ##### Fabius F. Stayed 8 nights in Jul 2023 ### 10/10 Excellent #### Phoebe C. Sep 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy It was amazing! Beautiful place to go for the weekend. ##### Phoebe C. Stayed 2 nights in Sep 2025 ### 10/10 Excellent #### Lynda B. Nov 27, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great property Very nice accommodation. Beds are comfortable and showers were clean. Didn't spend much time there due to family. ##### Lynda B. Stayed 7 nights in Nov 2022 ### 10/10 Excellent #### Loritha M. Oct 29, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### First time Vrbo renter very pleased! The location on Highland Lake with beautiful views and wildlife sightings was a wonderful retreat. As a first time Vrbo customer, I picked a great property and Ben was very patient will all my questions as well as accommodating. Everyone enjoyed the property and our time together! ##### Loritha M. Stayed 8 nights in Oct 2022 ### 10/10 Excellent #### Joe H. Sep 28, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great rental and location Perfect place for a family reunion ##### Joe H. Stayed 4 nights in Sep 2022 ### 10/10 Excellent #### Kim C. Sep 21, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Family Weekend We had a wonderful time at the lake house. Ben was wonderful! Excellent communication! The house was more than enough room for everyone! We were able to enjoy the backyard fire pit and roast marshmellows! We saw a bald eagle and a fox came to visit each morning! Wish we could have stayed longer! ##### Kim C. Stayed 3 nights in Sep 2022 ### 10/10 Excellent #### Jennifer S. Aug 19, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful property with great views We stayed for a week while our daughter attended a ballet summer program nearby. The home was just as shown in the photos. Ben was very easy to deal with during the reservation process and during our stay. Swam in the lake and took a lot of long walks - beautiful area and the home was comfortable and just what we were looking for. ##### Jennifer S. Stayed 6 nights in Jul 2022 ### 10/10 Excellent #### Carmen T. Aug 11, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great times at the lake It was an excellent experience for the family and felt like home way from home. Every detail was taken care of, and the host was available to reach out to whenever we needed. It overall exceeded our expectations. ##### Carmen T. Stayed 4 nights in Aug 2022 ### 10/10 Excellent #### sarah t. Jul 25, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### A Lakeside Retreat This is an absolutely beautiful, comfortable, well equipped home. It sits at the top of a long drive where, at the end, you have your own private dock on the most beautiful dock I've ever seen. We loved spending all day outside and all night on the couch watching tv and movies. A highlight was watching the sunrise from the dock on the lake on one of our first nights. The host was super easy to communicate with and helped us fix any minor problems we came across. Would stay again in a heartbeat! ##### sarah t. 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