Best Vacation Homes in Windsor
8 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $587/Night
For 7 Nights US $4,106
355.21 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $176/Night
For 7 Nights US $1,230
US $110/Night
For 7 Nights US $772
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
US $517/Night
For 7 Nights US $3,616
1367.02 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Parking
US $176/Night
For 7 Nights US $1,232
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $434/Night
For 7 Nights US $3,039
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $294/Night
For 7 Nights US $2,060
1500 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $230/Night
For 7 Nights US $1,612
Windsor Luxury Rentals
3896.54 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Oceanfront
- Spa
- Pool
US $1,222/Night
For 7 Nights US $8,552
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $591/Night
For 7 Nights US $4,136
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $528/Night
For 7 Nights US $3,693
3196.88 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $520/Night
For 7 Nights US $3,642
2798.62 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $510/Night
For 7 Nights US $3,569
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $444/Night
For 7 Nights US $3,111
3003.13 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $438/Night
For 7 Nights US $3,067
2798.62 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $387/Night
For 7 Nights US $2,708
Windsor Pet Friendly Vacation Rentals
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $156/Night
For 7 Nights US $1,092
US $61/Night
For 7 Nights US $428
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $188/Night
For 7 Nights US $1,318
359.99 ft²
9 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Breakfast
- Pet Friendly
US $114/Night
For 7 Nights US $799
1600 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $230/Night
For 7 Nights US $1,613
3900 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $386/Night
For 7 Nights US $2,699
2170 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $182/Night
For 7 Nights US $1,274
3900 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $331/Night
For 7 Nights US $2,314
Windsor Large Vacation Homes
10 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $165/Night
For 7 Nights US $1,152
2798.62 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $344/Night
For 7 Nights US $2,405
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $210/Night
For 7 Nights US $1,469
2798.62 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $336/Night
For 7 Nights US $2,349
Why Choose Rent By Owner for your Windsor 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
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as the region offers different attractions and weather conditions throughout the year, making it ideal to plan your stay when local events and seasons align with your vacation preferences.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild and pleasant weather, making it an ideal time for outdoor activities and exploring local scenery.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Fall (September to November)
Autumn offers comfortable temperatures and vibrant foliage, perfect for enjoying the tranquil ambiance and scenic views.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The quiet winter months bring cooler temperatures, providing a peaceful setting for those seeking solitude or cozy accommodations.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Late Summer (August)
As summer winds down, the region sees fewer visitors, offering a more relaxed experience with warm days and fewer crowds.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Weekly Weather Forecast for Windsor
How to Book Your Windsor 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
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 outdoor lounging areas such as patios or decks to relax while taking in the scenic views of the region.
- Benefit from spacious yards or gardens perfect for outdoor activities or family gatherings in this welcoming destination.
- Make use of private or community pools to cool off during warm summer days here.
- Take advantage of outdoor grills or BBQ stations for preparing meals alfresco and enhancing your local experience.
- Explore nearby nature trails or walking paths accessible from many vacation rentals in this area.
- Participate in recreational sports with amenities like volleyball courts, badminton setups, or basketball hoops often available on the premises.
- Relax by waterfront features such as docks or piers, especially if your rental is near lakes or rivers here in the region.
Top Attractions Around Windsor
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and local attractions that showcase the charming character of Windsor and its surrounding region.
Family Activities
- Windsor County Park: Enjoy a family picnic and outdoor activities amidst scenic trails and open green spaces in this peaceful park nearby.
- North Carolina Maritime Museum: Dive into the region’s maritime history through engaging exhibits that captivate both kids and adults alike.
- Downtown Windsor: Explore charming local shops, dine at family-friendly restaurants, and experience the small-town charm of this inviting area.
- Windsor Community Center: Participate in family-focused events and recreational programs designed to create memorable experiences for all ages.
Adult Activities
- Windsor Waterfront Park: Take a leisurely stroll or enjoy a relaxing picnic along the scenic waterfront, offering picturesque views and peaceful surroundings.
- North Carolina Maritime Museum: Dive into the region’s maritime history through engaging exhibits that provide insight into the area's rich nautical heritage.
- Local Golf Courses: Play a round at nearby golf courses designed to challenge enthusiasts and provide a pleasant day outdoors.
- Historic Downtown Windsor: Explore charming shops, dine at local eateries, and immerse yourself in the authentic southern atmosphere of this destination.
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the area's unique outdoor spaces and cultural sites to enrich your stay in Windsor.
- Plan Your Visit During Off-Peak Seasons: Visiting during quieter times allows for a more relaxed experience of the local scenery and amenities.
- Book Well in Advance: Secure your preferred vacation rentals early to ensure availability, especially during popular travel periods.
- Embrace the Regional Cuisine: Sample the regional flavors at local eateries or prepare authentic meals using ingredients sourced nearby to make your trip memorable.
Transportation Options
- Windsor Regional Airport: This airport offers convenient flights for travelers visiting the area, making it an accessible starting point for your trip.
- Taxi Services: Reliable taxi options are available to transport you comfortably from here to your vacation rental or nearby attractions.
- Local Bus Transit: The regional bus system provides an affordable and easy way to explore the surroundings without the need for a car.
- Car Rentals: Several car rental companies operate in this destination, giving you the flexibility to discover the region at your own pace.
Local Customs Options
- Local Seafood Cuisine: You can experience the region's fresh seafood traditions through local eateries and festivals in this area, reflecting its rich maritime heritage.
- Southern Hospitality Etiquette: Visitors often find that warm welcomes and polite interactions are a hallmark here, embodying the friendly spirit of southern North Carolina.
- Community Festivals and Fairs: Participating in seasonal events showcases the area's cultural pride and offers authentic experiences rooted in local customs.
- Historical Preservation Practices: Respect for historical sites and local landmarks is common, emphasizing the community’s dedication to maintaining its regional history.
Frequently Asked Questions About Windsor?
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor 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:
- The little cabin on the mountainside
- Waterfront Home with Pier on Albemarle Beach
- Cozy farm guest house…
- Reel'em Inn is a cozy river front fishing cottage on the Cashie River.
- THE HARDISON HOUSE in Historical Edenton the "South's Prettist Little Town"
- "Country Farm House"
- Water Front Cottage
- Cozy little guest house on Turkey Creek Farm!
- Fantastic WATERFRONT house with BEAUTIFUL VIEWS OF THE ALBEMARLE SOUND. Relaxing
- A remote getaway . Enjoy nature, have fun and embrace relaxation!
2. Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, 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:
3. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 74 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.
4. What is the cancellation policy for booking a vacation rental in Windsor, North Carolina?
Cancellation policies vary depending on the specific listing. You should review the cancellation terms outlined in the property details or contact the host directly to understand any potential fees or restrictions.
5. How do I confirm availability and book a vacation rental in Windsor, North Carolina?
Availability can be checked through the property listing. Once you find a suitable option, you can proceed with booking online or reach out to the host for further assistance.
6. Are there specific check-in and check-out times for rentals here?
Check-in and check-out times are set by each host and are listed within the property details. Be sure to review these before confirming your reservation to ensure they align with your travel plans.
7. What amenities are typically included in a vacation rental in Windsor, North Carolina?
Amenities vary between properties, but common features often include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Review the listing carefully to see which amenities are offered and meet your needs.
8. How do I get support if I encounter issues during my stay or booking process?
Customer support is available through the booking platform or directly from the property host. Contact details are provided in your reservation confirmation or on the property listing for prompt assistance.
Windsor Top Rated Vacation Rentals
US $101/Night
For 7 Nights US $704
US $133/Night
For 7 Nights US $933
322.92 ft²
6 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $170/Night
For 7 Nights US $1,192
US $105/Night
For 7 Nights US $736
US $76/Night
For 7 Nights US $532
US $112/Night
For 7 Nights US $784
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $219/Night
For 7 Nights US $1,535
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $210/Night
For 7 Nights US $1,469
