Compare Vacation Rentals & Rent By Owner Homes in Windsor County, Vermont, USA
About Windsor County Vacation Rentals
With more than 2104 Windsor County 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 Windsor County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windsor County, 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 Windsor County. Places to stay near Windsor County are 1120.07 ft² on average, with prices averaging US $561 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Windsor County 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 Windsor County, VT
Windsor County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windsor County?
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- Charming Log Cabin Apartment in Woodstock Village
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Vermont Winter Getaway
- Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
- 11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
How many Rentbyowner vacation rentals are available in Windsor County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2104 in the Windsor County 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 Windsor County.
