Compare Vacation Rentals & Rent By Owner Homes in Highland Lake, Winsted, Connecticut, USA
About Highland Lake Vacation Rentals
With more than 44 Highland Lake vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Highland Lake.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Highland Lake, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Highland Lake. Places to stay near Highland Lake are 638 ft² on average, with prices averaging US $338 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Highland Lake with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Highland Lake?
What are the top vacation rentals in Highland Lake?
- Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
- Our Cottage - Small in size, Big in character, On beautiful Highland Lake
- Family House On Highland Lake with Dock
- SPRING 2025! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat
- Newly renovated year-round LAKEFRONT rental on Highland Lake! Sleeps 8-9!
- Relax in The Farmhouse on a a beautiful land & pond
- The Cottage at Highland Lake, year-round, waterfront with a boat dock
- Unique & extraordinary experience - renew your senses. Delightful waterfront!
- Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
- Stunning Retreat on 62 Acres, 7000 sq ft, Pool and Hot Tub
How many Rentbyowner vacation rentals are available in Highland Lake?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 44 in the Highland Lake area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland Lake.
Nearby Neighborhood (4)
| Neighborhood | Property Count |
|---|---|
| Northwest Harwinton Vacation Rentals in Winsted, Connecticut | 51 |
| Collinsville Vacation Rentals in Winsted, Connecticut | 46 |
| Canton Valley Vacation Rentals in Winsted, Connecticut | 53 |
| Pleasant Valley Vacation Rentals in Winsted, Connecticut | 35 |
