8/10 Good
Karen C.
Mar 18, 2026
Liked: Cleanliness
Karen C.
Stayed 2 nights in Feb 2026
Entire home
Waterfront Cottage at Highland Lake w/dock
Choose dates to view prices
Photo gallery for Waterfront Cottage at Highland Lake w/dock
Reviews
9.49.4 out of 10
Exceptional
Entire home
3 bathroomsSleeps 4
Popular amenities
- Kitchen
- Free WiFi
- Air conditioning
- Outdoor Space
- Parking available
- Barbecue grill
Explore the area
Winsted, CT
- Highland LakePlace, Highland Lake2 min walk
- Winchester Historical SocietyPlace, Winchester Historical Society11 min walk
- Northwestern Connecticut Community CollegePlace, Northwestern Connecticut Community College2 min drive
- Hartford, CT (BDL-Bradley Intl.)Airport, Hartford, CT (BDL-Bradley Intl.)37 min drive
Room options
About the neighborhood
Winsted
This cottage places you next to Highland Lake and within a 10-minute walk of The Marina at Highland Lake. The cottage includes a kitchen, a balcony, and a refrigerator.
What's nearby
- Highland Lake - 2 min walk - 0.1 miles
- Winchester Historical Society - 11 min walk - 0.6 miles
- Walker Field - 18 min walk - 1.0 mile
- Northwestern Connecticut Community College - 2 min drive - 1.2 miles
- American Mural Project - 3 min drive - 1.4 miles
Getting around
- Bradley Intl. Airport (BDL) - 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
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Waterfront Cottage at Highland Lake w/dock
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.
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.
The cottage is air-conditioned and features a kitchen, 2.5 bathrooms, and a balcony. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a coffee maker, an ironing board, and a desk. Limited housekeeping is available.
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Property amenities
Beach
- Beach nearby
- Beach loungers
- Beach towels
Internet
- Available in the cottage: Free WiFi
Parking and transportation
- Car not required
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Electric kettle
- Kitchen island
- Microwave
- Oven
- Paper towels
- Refrigerator
- Spices
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- Bedsheets provided
Bathroom
- 2.5 bathrooms
- Hair dryer
- Shampoo
- Shower
- Soap
- Toilet paper
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- Smart TV
- Stereo
Outdoor areas
- Balcony
- Barbecue grill
- Dock
- Firepit
- Garden
- Outdoor furniture
Work spaces
- Desk
Comfort
- Air conditioning
- Heating
Pets
- No pets allowed
Suitability/Accessibility
- If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
- 1 step to reach entrance
- Handrails in stairways
- Smooth flooring in public areas
- Thin carpet in public areas
- Upper floors accessible by stairs only
- Smoking not allowed
Services and conveniences
- Iron/ironing board
- Limited housekeeping
Location highlights
- In the city center
- Near a hospital
- Near the marina
- On a lake
- On the waterfront
Things to do
- Boat
- Kayak
- Water sports equipment
- Birdwatching nearby
- Fishing nearby
- Hiking/biking trails nearby
- Kayaking nearby
- Motor boating nearby
- Swimming nearby
- Water skiing 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
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 18
Check-out
Check-out before 11:00 AM
Contactless check-out available
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
-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.
Pets
- This property doesn't allow pets
Children and extra beds
Children allowed: ages 0-17
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
- Check-in: 4:00 PM
- Check-out: 11:00 AM
- Minimum check-in age: 18
We should mention
Details about charges, deposits, or other important information:
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
- This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
- Charges for extra guests may apply and vary depending on the property's policy.
- A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
- Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
- Onsite parties or group events are strictly prohibited.
- Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Additional information about polices, regulations, and more:
- Long-term renters welcome.
- There are no elevators.
Property is also known as
482019
Frequently asked questions
What's there to do around this cottage?
This cottage in Winchester is within a 10-minute walk of Highland Lake and The Marina at Highland Lake. You'll also find Burr Pond State Park and American Mural Project within a short drive.
Is parking available on site at this cottage?
No, there isn't parking available at the cottage.
Is this cottage associated with a casino?
No, this cottage is not connected to a casino.
Is there an indoor pool at this cottage?
No, there is no indoor pool at this cottage.
What do couples enjoy most about Waterfront Cottage at Highland Lake w/dock?
Amenities that appeal to couples at this lakeside cottage include a kitchen and a smart TV in each accommodation with some featuring lake views.
Are there hot tubs at Waterfront Cottage at Highland Lake w/dock?
No, there isn't a spa tub at this cottage.
Does this cottage include breakfast service?
No, this cottage doesn't offer breakfast.
Does this cottage allow pets to stay for free?
No, pets aren't allowed at this cottage.
Does this cottage have connecting rooms?
No, this cottage doesn't feature connecting guestrooms.
Where is the closest airport to this cottage?
The closest major airport to this cottage is Bradley Intl. Airport (BDL), which is 26.1 mi away (48 minutes by car). Another top airport is Westfield, MA (BAF-Barnes Municipal), which is around 25.3 mi away.
Can I book a room with a balcony at Waterfront Cottage at Highland Lake w/dock?
Yes, every accommodation at Waterfront Cottage at Highland Lake w/dock comes with a balcony with some featuring lake views.
Waterfront Cottage at Highland Lake w/dock Reviews
Reviews
9.4
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 10 out of 12 reviews
10 - Excellent
10
Rating 8 - Good. 1 out of 12 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 12 reviews
6 - Okay
0
Rating 4 - Poor. 1 out of 12 reviews
4 - Poor
1
Rating 2 - Terrible. 0 out of 12 reviews
2 - Terrible
0
9.6/10
Cleanliness
Reviews
10/10 Excellent
Doug J.
Nov 16, 2025
Liked: Cleanliness
Very clean and comfortable. Great view! Thank you.
Doug J.
Stayed 3 nights in Nov 2025
10/10 Excellent
Vanessa K.
Oct 28, 2025
Liked: Cleanliness
We arrived early and had no problem communicating with the host. Very cute place.
Vanessa K.
Stayed 2 nights in Oct 2025
4/10 Poor
John C.
Oct 22, 2025
Liked: Cleanliness
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
10/10 Excellent
Jim B.
Oct 1, 2025
Liked: Cleanliness
Great place!
Jim B.
Stayed 2 nights in Sep 2025
10/10 Excellent
Samara S.
Sep 7, 2025
Liked: Cleanliness
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.
Samara S.
Stayed 2 nights in Sep 2025
10/10 Excellent
Michelle H., Burlington, MA
Apr 27, 2025
Liked: Cleanliness
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.
Michelle H.
Stayed 2 nights in Apr 2025
10/10 Excellent
Robert B.
Apr 20, 2025
Liked: Cleanliness
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!!
Robert B.
Stayed 3 nights in Apr 2025
10/10 Excellent
Margaret T.
Sep 14, 2024
Liked: Cleanliness
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.
Margaret T.
Stayed 4 nights in Sep 2024
10/10 Excellent
joyce w.
May 23, 2024
Liked: Cleanliness
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.
joyce w.
Stayed 6 nights in May 2024
10/10 Excellent
Lori C.
Nov 2, 2023
Liked: Cleanliness
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!
Lori C.
Stayed 2 nights in Oct 2023
10/10 Excellent
Charles C.
Jun 23, 2023
Liked: Cleanliness
Nice
Stay was great but the road to the location is a little rough.
Charles C.
Stayed 4 nights in Jun 2023