Best Vacation Homes in Windsor Hills
House
10.0(104 Reviews)
3 Bedrooms
3 Baths
6 Guests
2400 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $480/Night
7 Nights - US $3,363
Apartment
9.2(5 Reviews)
1 Bedroom
1 Bath
2 Guests
861.11 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Internet
US $146/Night
7 Nights - US $1,022
US $115/Night
7 Nights - US $802
House
10.0(33 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $212/Night
7 Nights - US $1,487
Apartment
1.0(1 Review)
1 Bedroom
1 Bath
3 Guests
1001.04 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $238/Night
7 Nights - US $1,666
Condo
10.0(22 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Pet Friendly
US $178/Night
7 Nights - US $1,244
Apartment
10.0(21 Reviews)
1 Bedroom
1 Bath
2 Guests
860 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $196/Night
7 Nights - US $1,370
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $346/Night
7 Nights - US $2,419
Windsor Hills Luxury Rentals
House
10.0(1 Review)
6 Bedrooms
5 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $1,279/Night
7 Nights - US $8,953
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
Pool- Kitchen
- Parking
US $500/Night
7 Nights - US $3,498
House
9.4(12 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $410/Night
7 Nights - US $2,869
House
3 Bedrooms
3 Baths
6 Guests
2131.25 ft²
Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $375/Night
7 Nights - US $2,625
House
2 Bedrooms
3 Baths
4 Guests
1797.57 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Parking
US $372/Night
7 Nights - US $2,604
House
9.6(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
2127 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $361/Night
7 Nights - US $2,527
House
10.0(4 Reviews)
2 Bedrooms
3 Baths
4 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $299/Night
7 Nights - US $2,091
Condo
10.0(8 Reviews)
4 Bedrooms
3 Baths
12 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $253/Night
7 Nights - US $1,773
Windsor Hills Pet Friendly Vacation Rentals
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $222/Night
7 Nights - US $1,555
Apartment
2 Bedrooms
3 Baths
4 Guests
1496.18 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $207/Night
7 Nights - US $1,451
Apartment
9.2(123 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $102/Night
7 Nights - US $715
Apartment
10.0(12 Reviews)
2 Bedrooms
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $122/Night
7 Nights - US $857
Hotel
9.4(51 Reviews)
9 Baths
333.68 ft²
Oceanfront- Fireplace/Heating
- Pool
Ocean View
US $140/Night
7 Nights - US $981
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $175/Night
7 Nights - US $1,228
House
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $153/Night
7 Nights - US $1,070
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
US $169/Night
7 Nights - US $1,182
Windsor Hills Large Vacation Homes
House
3 Bedrooms
1 Bath
12 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $189/Night
7 Nights - US $1,323
Apartment
7.3(21 Reviews)
23 Bedrooms
3 Baths
6 Guests
753.47 ft²
- Fireplace/Heating
View- Pet Friendly
- Parking
US $153/Night
7 Nights - US $1,072
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $258/Night
7 Nights - US $1,808
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1092 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $308/Night
7 Nights - US $2,154
House
4 Bedrooms
4 Baths
11 Guests
5000 ft²
- Pet Friendly
- Kitchen
Air Conditioner- Internet
US $504/Night
7 Nights - US $3,528
Why Choose Rent By Owner for your Windsor Hills Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windsor Hills
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you can fully enjoy all that this destination has to offer, making your stay in Windsor Hills, Roanoke, Virginia, a truly memorable experience.
Peak Season Highlights
Late Spring to Early Summer (May - June)
This is the time when the region experiences warm weather, making it ideal for exploring outdoor activities and enjoying the local scenery.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September - October)
During early fall, the area offers pleasant temperatures and fewer crowds, perfect for a relaxed visit while still enjoying comfortable weather.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December - February)
The winter months see cooler temperatures, providing a peaceful atmosphere and potentially lower rates on vacation rentals here.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Late Fall (November)
As the region transitions into winter, you can experience quieter surroundings and more budget-friendly options, ideal for those seeking tranquility.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Windsor Hills
How to Book Your Windsor Hills Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor Hills
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to well-maintained outdoor swimming pools that provide a refreshing retreat during your stay.
- Take advantage of beautifully landscaped communal gardens and picnic areas ideal for relaxing afternoons outdoors.
- Benefit from dedicated tennis courts and sports facilities perfect for active recreation in the local region.
- Utilize the walking and biking trails that wind through the community, offering scenic routes to explore here.
- Make use of the outdoor playgrounds and spaces specially designed for family fun and children’s activities.
- Relax by the outdoor lounge areas with comfortable seating, ideal for socializing or enjoying the fresh air.
- Access to well-equipped outdoor barbecue stations allows you to host enjoyable cookouts in this welcoming destination.
Top Attractions Around Windsor Hills
What attractions are nearby?
In this charming region, you can explore a variety of outdoor activities and cultural attractions that provide an engaging experience for visitors seeking to enjoy the natural beauty and local heritage near Windsor Hills.
Family Activities
- Virginia Museum of Transportation: Explore the area's rich automotive history through interactive exhibits and vintage vehicles, perfect for engaging family outings.
- Roanoke Greenway Trails: Enjoy a family-friendly adventure along scenic trails that wind through this destination’s natural beauty, ideal for biking and walking excursions.
- Mill Mountain Zoo: Spend a day at the zoo to see native and exotic animals, providing educational fun for children and adults alike in this region.
- Local Farmers Markets: Discover fresh local produce and handmade crafts at the area’s vibrant farmers markets, offering a delightful cultural experience for families visiting here.
Adult Activities
- Virginia Museum of Transportation: Dive into the region’s rich history with fascinating exhibits and vintage vehicles that showcase this area's transportation heritage.
- Roanoke Star and Mill Mountain Park: Enjoy panoramic views of the surrounding landscape while taking a scenic hike or relaxing at this iconic landmark in the region.
- Taubman Museum of Art: Explore captivating contemporary and classic artworks that reflect the artistic spirit of this destination’s vibrant community.
- Carvins Cove Natural Reserve: Engage in outdoor adventures like hiking, mountain biking, or fishing at this expansive natural area nearby.
Windsor Hills Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of nearby points of interest to enrich your stay and truly experience the charm of this destination.
- Plan Your Activities: Incorporate leisurely outings or outdoor adventures to make the most of your time in the area’s scenic surroundings.
- Choose a Prime Location: Select your vacation rental in a central spot to easily access key sites and enjoy convenience throughout your visit.
- Connect with Local Resources: Reach out to hosts or local guides for personalized tips that can enhance your experience while staying here.
Transportation Options
- Driving your own vehicle: You can easily navigate the area with a reliable car, providing flexibility to explore Windsor Hills and its nearby attractions at your own pace.
- Regional taxi services: Professional taxi companies operate in Roanoke, offering convenient transportation options for getting around within the city and to surrounding areas.
- Public transit options: Local bus routes connect key destinations in the region, making it an economical choice for travel without the need for a private vehicle.
- Ride-sharing services: Apps like Uber and Lyft are readily available here, offering quick and dependable transportation when you prefer not to drive yourself.
Local Customs Options
- Southern Hospitality: Visitors here often experience warm welcomes and courteous exchanges that reflect the area's friendly community spirit.
- Local customs include celebrating regional crafts and music, offering a glimpse into the region's rich cultural heritage.
- Food and Dining Etiquette: Enjoying hearty Southern cuisine is common, with a focus on hospitality and sharing meals with neighbors and new friends alike.
- Participating in or observing local religious festivals and ceremonies provides insight into the spiritual fabric of this destination.
Windsor Hills Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Windsor Hills?
There are a lot of options in Windsor Hills. If you plan on staying in the Windsor Hills 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 Hills:
- Historic Home on the Greenway near Grandin Village & Downtown Roanoke.
- Beautiful Renovated Lake Cottage in SW County and only minutes from Downtown!
- 2BR Historic Apt - Safe|Walkable|Food|Greenway
- Idyllic Cave Spring Studio w/Patio & Fire Pit!
- Charming 3-bedroom house in Roanoke with fitness area, lots of space. Sleeps 6
- Roanoke Home Downtown Charm near Greenways
- The West End Flats
- Sleek loft minutes from downtown
- 1BR Penthouse Apt |Walkable|Food|Greenway|Safe
- Stylish 1BR near brews & downtown
2. How many vacation rentals have private pools in Windsor Hills?
There are 1 vacation rentals with private pools near Windsor Hills. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor Hills are best for families?
If you are looking for a family-friendly vacation home in Windsor Hills, 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 Hills:
4. How many Rentbyowner vacation rentals are available in Windsor Hills?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 139 in the Windsor Hills 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 Hills.
5. What is the cancellation policy for vacation rentals in Windsor Hills, Roanoke?
Cancellation policies vary by property. You should review the specific cancellation terms listed on the rental listing or contact the owner directly to understand your options and any potential fees.
6. How do I confirm my booking for a vacation rental in the area?
Booking confirmation typically occurs after completing the reservation process and receiving a confirmation email from the host. Make sure to follow all steps outlined in the listing to secure your stay.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning fees, service charges, or security deposits may apply and are usually detailed on the property listing. It’s best to review these details before finalizing your reservation.
8. What amenities are usually included in vacation rentals in the region?
Most properties in this destination offer amenities like Wi-Fi, parking, air conditioning, and fully equipped kitchens. Check the specific listing for a complete list of what’s included to ensure it meets your needs.
9. Can I contact the owner directly for special requests or questions about the property?
Yes, you can reach out to the property owner through the platform to inquire about special arrangements or clarify details about the vacation rental. Owners are typically responsive to guest inquiries to ensure a smooth stay.
Windsor Hills Top Rated Vacation Rentals
Hotel
9.4(972 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $138/Night
7 Nights - US $969
Hotel
8.7(158 Reviews)
1 Bath
262.95 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $131/Night
7 Nights - US $917
Hotel
8.2(204 Reviews)
8 Baths
322.92 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $126/Night
7 Nights - US $884
Hotel
8.1(197 Reviews)
1 Bath
373.51 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $157/Night
7 Nights - US $1,096
Hotel
7.8(827 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $113/Night
7 Nights - US $794
Hotel
7.3(259 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $113/Night
7 Nights - US $791
US $89/Night
7 Nights - US $625
House
9.8(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $368/Night
7 Nights - US $2,578
