Compare Vacation Rentals & Rent By Owner Homes in Winchester, Winsted, Connecticut, USA
About Winchester Vacation Rentals
With more than 41 Winchester 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 Winchester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Winchester, 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 Winchester. Places to stay near Winchester are 702.57 ft² on average, with prices averaging US $326 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Winchester, CT
Winchester Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Winchester?
- 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
- Lakefront Tranquility/Fishermans Delight
- Newly renovated year-round LAKEFRONT rental on Highland Lake! Sleeps 8-9!
- The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
- Charming 2-bedroom cottage with AC and WiFi in welcoming New Hartford
- Unique & extraordinary experience - renew your senses. Delightful waterfront!
- Best Outdoors near the Berkshires
- The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 41 in the Winchester 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 Winchester.
