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Family House On Highland Lake with Dock

Photo gallery for Family House On Highland Lake with Dock

Front of home
Waterfront deck and dock
Master bedroom with king sized bed and screened in porch
Dining room
Seating area

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms3+ bathroomsSleeps 122000 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Winsted, CT
  • Place, Highland Lake
    ‪2 min walk‬
  • Place, The Marina at Highland Lake
    ‪13 min walk‬
  • Place, Winchester Historical Society
    ‪19 min walk‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪39 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

2 Single Beds

Bedroom 5

1 Queen Bed

Living Room

1 Queen Bed

Master Bedroom

1 King Bed

3 bathrooms, 1 half bathroom

Bathroom 4

Downstairs half bath

Toilet

Master Bathroom

Bathtub · Toilet · Shower only

Upstairs full bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

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
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
No oversized/ large commercial vehicles or excessive number of vehicles.

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

About the area

Winsted

Located in Winchester, this holiday home is on the beach. Winchester Historical Society and American Mural Project are cultural highlights, and travellers looking to shop may want to visit Ledgebrook Plaza and Ames Plaza Shopping Center. Laurel Lanes and KidsPlay Museum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
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

  • Hartford, CT (BDL-Bradley Intl.) - 50 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Subway - ‬8 min drive
  • ‪Little Red Barn Brewer - ‬19 min walk
  • ‪Dunkin' - ‬6 min drive

Frequently asked questions

Is Family House On Highland Lake with Dock pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Family House On Highland Lake with Dock?

As of 16 Mar 2026, prices found for a 1-night stay for 2 adults at Family House On Highland Lake with Dock on 18 Mar 2026 start from £198, 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 Family House On Highland Lake with Dock?

On-site parking is available at the property.

What time is check-in at Family House On Highland Lake with Dock?

Check-in begins at 4:00 PM.

What time is check-out at Family House On Highland Lake with Dock?

Checkout is at 10:00 AM.

Where is Family House On Highland Lake with Dock located?

Situated on the beach, this holiday home is within a 15-minute walk of Highland Lake and The Marina at Highland Lake. Winchester Historical Society and Laurel Lanes are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 26 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Phoebe C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was amazing! Beautiful place to go for the weekend.
Stayed 2 nights in Sep 2025

10/10 Excellent

Jason B.

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.
Stayed 3 nights in Jan 2025

10/10 Excellent

TJ M.

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.
Stayed 7 nights in Jun 2025

10/10 Excellent

Karen A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Work trip

Great location and great accommodations!
Stayed 2 nights in Feb 2024

10/10 Excellent

Sasha A.

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
Stayed 2 nights in Aug 2023

10/10 Excellent

Patricia C.

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.
Stayed 4 nights in Aug 2023

10/10 Excellent

jeff c.

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!
Stayed 3 nights in Jun 2024

10/10 Excellent

Scott B.

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.
Stayed 4 nights in Aug 2024

10/10 Excellent

Jeffrey

Liked: Cleanliness, amenities, property conditions & facilities, communication
The property was perfect for our needs. Instructions for everything was provided fabulous rental.
Stayed 2 nights in Apr 2024

10/10 Excellent

Kathy G.

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!
Stayed 7 nights in Jun 2024

10/10 Excellent

brett c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stey

Amazing view. Great price. Great communication.
Stayed 4 nights in May 2024

10/10 Excellent

Caitlin L.

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!
Stayed 3 nights in May 2024

10/10 Excellent

Verified traveller

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!
Stayed 7 nights in Aug 2023

10/10 Excellent

Lorraine A.

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!
Stayed 3 nights in Dec 2022

10/10 Excellent

Kimberly S.

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!!
Stayed 7 nights in Jul 2023

8/10 Good

Fabius F.

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.
Stayed 8 nights in Jul 2023

10/10 Excellent

Jackie O.

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!
Stayed 3 nights in Jul 2024

8/10 Good

Wendy B.

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
Dining area
Boating
Stayed 7 nights in Aug 2025

10/10 Excellent

Lynda B.

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.
Stayed 7 nights in Nov 2022

10/10 Excellent

Loritha M.

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!
Stayed 8 nights in Oct 2022

10/10 Excellent

Joe H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great rental and location

Perfect place for a family reunion
Stayed 4 nights in Sep 2022

10/10 Excellent

Kim C.

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!
Stayed 3 nights in Sep 2022

10/10 Excellent

Jennifer S.

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.
Stayed 6 nights in Jul 2022

10/10 Excellent

Carmen T.

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.
Stayed 4 nights in Aug 2022

10/10 Excellent

sarah t.

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!
Stayed 7 nights in Jul 2022

About the host

Hosted by Ben

Host profile image
Hi, I'm your host, Ben.

I recently bought and renovated this home so that you can have the perfect summer vacation with your family this summer, or spend a crisp fall weekend here to see the beautiful colors of the leaves, or a hiking trip with some friends, the Highland Lake area has so much to offer, all year round.

When I'm not spending time at the house in Connecticut, I can be found skiing, playing soccer, with my friends, spending time with my niece and nephew, traveling the world, or cooking for friends and family.

Why they chose this property

Not only is there so much to do in the area, this house is located right on Highland Lake. I loved that while viewing the house I could picture myself and guests enjoying the dock in the summer, or watching the leaves change colors on a weekend in the fall, and even using it as a place to stay while you ski in the area.

I hope that my home is a place where you and your family can relax, have fun, and make lasting memories, and come back year after year to experience all the area has to offer.



What makes this property unique

The house is right on Highland Lake, it is a short walk from a brewery, there are many antiquing options in the area, fly fishing, river rafting, hiking, skiing, boating, and more.

Languages:

English

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