Entire home
Best Outdoors near the Berkshires
Winsted vacation home with kitchen
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Reviews
9.8 out of 10
Exceptional
Entire home
1 bedroom1 bathroom900 sq ft
Popular amenities
Explore the area
Winchester, CT
- Place, Winchester Historical Society6 min walk
- Place, Highland Lake13 min walk
- Place, Northwestern Connecticut Community College15 min walk
- Airport, Hartford, CT (BDL-Bradley Intl.)40 min drive
Room options
About the neighborhood
About this property
Similar properties

Waterfront Cottage at Highland Lake w/dock
Winsted
Waterfront Cottage at Highland Lake w/dock
- Kitchen
- Free WiFi
- Air conditioning
- Outdoor Space
4.7 out of 5, Exceptional, 12 reviews
Property amenities
Policies
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 are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a private host, not a professional engaged in trade or business. 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. Onsite parties or group events are strictly prohibited. Long-term renters welcome. For guests' safety, the property includes a smoke detector in each accommodation.
Frequently asked questions
Best Outdoors near the Berkshires Reviews
Reviews
9.8
Exceptional
10/10
Cleanliness
Reviews
May 1, 2026
Liked: Cleanliness
Stayed 2 nights in Apr 2026
10/10 Excellent
Lauren R., Austin, Texas, USA
Mar 30, 2026
Liked: Cleanliness
Lauren R.
Stayed 1 night in Mar 2026
10/10 Excellent
Mary C.
Mar 29, 2026
Liked: Cleanliness
Mary C.
Stayed 1 night in Mar 2026
10/10 Excellent
Paul S.
Mar 3, 2026
Liked: Cleanliness
Paul S.
Stayed 2 nights in Feb 2026
10/10 Excellent
Justine L., Hawley, Pennsylvania
Feb 10, 2026
Liked: Cleanliness


Justine L.
Stayed 2 nights in Feb 2026
10/10 Excellent
Leslie H.
Jan 1, 2026
Liked: Cleanliness
Leslie H.
Stayed 1 night in Dec 2025
10/10 Excellent
Rowland D.
Dec 30, 2025
Liked: Cleanliness
Rowland D.
Stayed 4 nights in Dec 2025
10/10 Excellent
Rachel B.
Nov 20, 2025
Liked: Cleanliness
Rachel B.
Stayed 1 night in Nov 2025
10/10 Excellent
Willow K.
Nov 17, 2025
Liked: Cleanliness


Willow K.
Stayed 2 nights in Nov 2025
10/10 Excellent
Madelaine L.
Nov 1, 2025
Liked: Cleanliness
Madelaine L.
Stayed 1 night in Oct 2025
10/10 Excellent
Scott G.
Oct 19, 2025
Liked: Cleanliness
Scott G.
Stayed 5 nights in Oct 2025
10/10 Excellent
Anne M.
Oct 1, 2025
Liked: Cleanliness
Anne M.
Stayed 1 night in Sep 2025
10/10 Excellent
Sean B.
Sep 14, 2025
Liked: Cleanliness
Sean B.
Stayed 1 night in Sep 2025
10/10 Excellent
Roberta W.
Sep 13, 2025
Liked: Cleanliness


Roberta W.
Stayed 1 night in Sep 2025
10/10 Excellent
Rachel B.
Aug 9, 2025
Liked: Cleanliness
Great stay
Rachel B.
Stayed 1 night in Aug 2025
8/10 Good
Jack H.
Jun 25, 2025
Liked: Cleanliness
Wonderful ambience.
Jack H.
Stayed 1 night in Jun 2025





