Windsor Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windsor, Vermont, USA

Meadow View- 35 Acres outside your door
10.0 (76 Reviews)
1 Bedroom 4 Guests
Luxury Vermont Vacation Rental Private Hot Tub!
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10.0 (1 Review)
4 Bedrooms 9 Guests
Sunset Cabin - your private romantic hideaway
10.0 (64 Reviews)
1 Bedroom 2 Guests
Snapdragon Inn
10.0 (8 Reviews)
2 Bedrooms 4 Guests
Long Range Mountain Views in West Windsor
10.0 (21 Reviews)
3 Bedrooms 6 Guests
Kennedy’s House
New
3 Bedrooms 4 Guests
Ascutney Mountain House
New
4 Bedrooms 8 Guests
Lovely Vermont Cabin on a quiet street
9.8 (6 Reviews)
3 Bedrooms 7 Guests
Green Mountains
4.9 (42 Reviews)
3 Bedrooms 8 Guests

About Windsor Vacation Rentals

With more than 22 Windsor 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.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windsor, 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. Places to stay near Windsor are 1646.35 ft² on average, with prices averaging US $742 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Windsor Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windsor?

How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 22 in the Windsor 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.