Welcome to The Cottage at Highland Lake! Relax at this cozy waterfront cottage. Updated! Now sleeps up to 6 people with a sleeper sofa on the 1st floor! 2nd floor, central air in bedrooms. There are two bedrooms and 1.5 bathrooms. There`s a boat dock, large deck, upper deck, grill, and beach area. The 1st floor has an open floor plan and includes a full kitchen, TV area with couches and a bar area. Long-term availability. Get 25% discount off all boat rentals at The Marina at Highland Lake.
The Cottage at Highland Lake sleeps up to 6 people. The master bedroom has a king bed with a deck. The 2nd bedroom has a bunk bed. There is a queen sleeper sofa on the first floor that sleeps 2 people. The 2nd floor has central air in both bedrooms and a full bath. There`s a boat dock, large deck, upper deck, grill, and beach area. The 1st floor has an open floor plan and includes a full kitchen, TV area with couches and a bar area and has a half bath.
I`m available by phone or text.
The neighborhood at Highland Lake is a fun outdoor part of Winsted. Located just minutes away from Main Street and Rowley Street, which offer delicious restaurants, cafes, and even a brewery right down the street with an incredible circuit of local food trucks. All of your watersport and leisure needs can be met by The Marina at Highland lake which offers rentals of pontoons, ski boats, kayaks, canoe, paddleboards, and captained evening pontoon cruises around the lake. There are multiple antique shops in and around Winsted, as well as local breweries and vineyards. For winter sports, there is ice fishing right on Highland Lake, and many nearby ski resorts within a half hour ride including: Ski Sundown, Mohawk Mountain, Ski Butternut, and Otis Ridge.
There is a shared right-of-way leading to a private parking area. -No smoking indoors. -Parties, events and large gatherings are not allowed during your stay. -Smoking, vaping and hookahs are not allowed. -Sorry, Pets are not allowed.
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Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
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Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
-No smoking indoors.
-Parties, events and large gatherings are not allowed during your stay.
-Smoking, vaping and hookahs are not allowed.
-Parties, events and large gatherings are not allowed during your stay.
-Sorry, Pets are not allowed.
-Please bring your own beach towels. They will not be provided.
Important information
You need to know
Property # 3322590vb
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
Long-term renters welcome
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Winsted
Located in Winsted, this cottage is in the city centre 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, waterskiing and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby.
Winchester Historical Society - 14 min walk - 1.2 km
Rowley Fields - 2 min drive - 1.5 km
Northwestern Connecticut Community College - 3 min drive - 1.8 km
Getting around
Hartford, CT (BDL-Bradley Intl.) - 48 min drive
Restaurants
McDonald's - 4 min drive
Dunkin' - 3 min drive
Subway - 7 min drive
Little Red Barn Brewer - 19 min walk
Dunkin' - 4 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 9 May 2026, prices found for a 1-night stay for 2 adults at Waterfront Cottage at Highland Lake w/dock on 6 Jan 2027 start from AU$481, 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 Waterfront Cottage at Highland Lake w/dock?
On-site 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?
Checkout 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 Laurel Lanes are also within 1 mile (2 km).
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
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.
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!!
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.
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.
joyce w.
Stayed 6 nights in May 2024
Response from VrboOwner on 15 Sept 2024
Thank you for staying with us. We're glad you enjoyed!
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!
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.
John C.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 16 Nov 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.
About the host
Hosted by Jeanne Richard
I've owned rental properties including yearly rentals and vacation rentals for over 10 years. I live and work local and am very responsive to the needs of my guests in order to enjoy their stay, whether it's two days or long term.
Why they chose this property
This property is located in the first of three bays of Highland Lake, which offers a peaceful cove, beautiful views, swimming, boating, fishing and much more, and can be enjoyed throughout the year.
What makes this property unique
This is a cozy cottage located right on the water. You can receive a 25% discount off any rentals during your stay right down the street at The Marina at Highland Lake. You have the added benefit of myself and my husband owning and working close by should any issues arise or if you have questions to further enhance the enjoyment of your stay.
Languages:
English
Premier Host
They consistently provide great experiences for their guests