Owner Direct Vacation
Rentals in Windsor County
The Best Owner Direct Vacation Rentals in Windsor County. Explore thousands of vacation home rentals, large cabins, and villas near Windsor County
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Explore the Best Windsor County Vacation Homes
Looking for the perfect place to stay in Windsor County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Windsor County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Windsor County Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Windsor County
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Popular Neighborhoods for Windsor County Vacation Rentals
What are the best areas to stay in Windsor County
Discover the top neighborhoods in Windsor County and choose a place that suits your stay.
Wednesday Feb 11
Windsor County, Vermont
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Windsor County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Windsor County
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How to Reserve Your Windsor County Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Windsor County Vacation Rental FAQs
1. What are the top vacation rentals in Windsor County?
There are a lot of options in Windsor County. If you plan on staying in the Windsor County area, consider making a reservation for a few nights at one of these properties as these have been rated 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
- 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
2. How many vacation rentals have private pools in Windsor County?
There are 64 vacation rentals with private pools near Windsor County. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Windsor County are best for families?
If you are looking for a family-friendly vacation home in Windsor County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor County:
4. How many vacation rentals are available in Windsor County?
Currently, the total number of properties listed in 2026 is over 2099 in the Windsor County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor County.