Compare Vacation Rentals & Rent By Owner Homes in Middlebury, Connecticut, USA
About Middlebury Vacation Rentals
With more than 99 Middlebury 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 Middlebury.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Middlebury, 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 Middlebury. Places to stay near Middlebury are 571.99 ft² on average, with prices averaging US $321 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Middlebury 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 Middlebury, CT
Frequently Asked Questions About Middlebury?
What are the top vacation rentals in Middlebury?
- Charming 1760 Cape Nestled in the Foothills of Litchfield County
- Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
- Small Town Stay- Stroll to Local Shops/Dining/Taft
- 6-Acre Luxurious Country Home with Goddess Point Lookout
- Cozy family and pet friendly 3BR Home
- Clean & Bright 2 Bedroom Cottage shares 8 Acres
- Private studio guesthouse in Watertown CT
- Historic Country Retreat in Litchfield County
- Private Apartment in Southbury 103
- Luxury King Suite in Waterbury. 3 Bedroom. Essentials Close-By,
How many Rentbyowner vacation rentals are available in Middlebury?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 99 in the Middlebury 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 Middlebury.
