Waterfront Cottage at Highland Lake w/dock

Photo gallery for Waterfront Cottage at Highland Lake w/dock

A marina with several boats docked, surrounded by residential houses with large windows and balconies.
A lakeside property with a dock, a small boat, and a wooden deck.
A two-story house with a deck, a garage, and a swimming pool.
A spacious living area with a wooden bar, a brown leather sofa, and a dining table with chairs.
A lakeside property with a dock, grassy lawn, and a house with a deck overlooking the water.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Close to Highland Lake

Popular amenities

  • Balcony
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Onsite parking available
  • Non smoking

Explore the area

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

Rooms & beds

0 bedrooms (sleeps 5)

Common Spaces

1 Twin Bunk Bed, 1 Double Sofa Bed and 1 King Bed

Living Room 1

1 Queen Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet

Bathroom 3

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms
Garden
Dining area

Add dates for prices

Similar properties

Interior
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
10.0 out of 10, Exceptional, (4 reviews)
Peaceful and cozy 1 bed 1 bath in quaint Winchester

About the neighborhood

Winsted

Located in Winsted, this cottage is in the city center and on the waterfront. The Marina at Highland Lake and Laurel Lanes are worth checking out if an activity is on the agenda, while those looking for area attractions can visit KidsPlay Museum and Action Wildlife Foundation. Flamig Farm and Thorncrest Farm & Milk House Chocolates are also worth visiting. Kayaking, water skiing, and motor boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
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Map
Winsted, CT

What's nearby

  • Highland Lake - 2 min walk - 0.2 km
  • The Marina at Highland Lake - 8 min walk - 0.7 km
  • Winchester Historical Society - 14 min walk - 1.2 km
  • Northwestern Connecticut Community College Library - 2 min drive - 1.9 km
  • Northwestern Connecticut Community College - 3 min drive - 1.8 km

Getting around

  • Bradley Intl. Airport (BDL) - 48 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin' - ‬3 min drive
  • ‪Arcadia - ‬11 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Skipper's - ‬3 min drive

Frequently asked questions

Is Waterfront Cottage at Highland Lake w/dock pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Waterfront Cottage at Highland Lake w/dock?

As of Nov 4, 2026, prices found for a 1-night stay for 2 adults at Waterfront Cottage at Highland Lake w/dock on Nov 5, 2026 start from $273, 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?

Onsite parking is available at the property.

What time is check-in at Waterfront Cottage at Highland Lake w/dock?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Cottage at Highland Lake w/dock?

Check-out is at 11:00 AM.

Where is Waterfront Cottage at Highland Lake w/dock located?

Located in the heart of Winsted, this cottage is within a 10-minute walk of Highland Lake and The Marina at Highland Lake. Winchester Historical Society and American Museum of Tort Law are also within 1 mi (2 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 1 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Loved sitting on the deck!!!!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Stayed 2 nights in Sep 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet and comfortable! Thank you
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We arrived early and had no problem communicating with the host. Very cute place.
Stayed 2 nights in Oct 2025
Response from VrboOwner on Nov 16, 2025
Thank you Gage for the review. We're glad you enjoyed and were able to accommodate his group for an earlier check-in.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check was easy and smooth, extra directions communicated were great, the use of water toys were wonderfully appreciated. We had a very short stay for an event but would highly recommend and would absolutely stay again.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and comfortable. Great view! Thank you.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

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

Nice weekend getaway

Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure.
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Lakefront Stay

We only came into town for a wedding, but we loved the lakefront cottage! It's an older home, but it was well kept and suited our needs perfect. We're hoping to "jump in the lake" the next time we stay. Thank you Jeanne for allowing us to check in early...we look forward to our next stay!!
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

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

Nice

Stay was great but the road to the location is a little rough.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

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

Awesome lakeside property

Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

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

waterfront property

happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water.
Stayed 6 nights in May 2024
Response from VrboOwner on Sep 15, 2024
Thank you for staying with us. We're glad you enjoyed!
Verified review

10/10 Excellent

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

Perfect Fall Getaway

My husband and I recently enjoyed a weekend at the Cottage at Highland Lake and would highly recommend it. The host gave excellent detailed directions, check in was easy, and the cottage was clean and exactly as described with a fully remodeled upstairs. There is a small deck off the master bedroom and a really nice size deck off the first floor, both overlooking the lake. Best of all is the location. The cottage is right on the lake and has a dock. Overall just a perfect weekend escape!
Stayed 2 nights in Oct 2023
Verified review

4/10 Poor

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy
We booked the cottage as a kayaking retreat approx one week in advance bc the weather outlook was excellent for the season. By all indications in the listing, the cottage was perfect for what we were there to accomplish. When we arrived the water level was extremely low due to a planned drawback which rendered the dock useless and even dangerous for our 3 young kids. The beach area was all muck, moss, and sharp rocks for several feet from the waters edge. This was NOT an act of nature, it was a planned water reduction so that homeowners could work on their docks, this measure was apparently enacted weeks before we arrived.. This information was NOT disclosed to us at the time of scheduling and it was not disclosed in the description. This planned event rendered the purpose of the cottage (as a lake house) nil. Communication with Jeanne proved absolutely fruitless. She took no responsibility for the non disclosure. There was no effort or willingness made to rectify OR comp the experience in anyway, only back peddled explanations and half hearted apologies. It was a very disappointing exchange considering our willingness to reason and settle. We were able to make the best of it by packing our gear and visiting burr pond a few miles away. It would’ve made more sense for us to drive there straight from our home... I would not recommend.
Stayed 2 nights in Oct 2025
Response from VrboOwner on Nov 16, 2025
I wanted to respond to John's negative review. Unfortunately Highland Lake was lowered this year deeper and earlier than usual. This is done every five years and I neglected to let John know this. I communicated and apologized to him several times. The water is cold in the end of October and is usually not used by renters and property owners. But I'm updating the listing to provide this information. The cottage itself was listed exactly as it was and could be used as is. John also brought a dog even though it is listed in the property listing as well as the house rules that pets are not allowed. My neighbors contacted me when it was running around outside onto their property.
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