Windsor holiday rentals

We found 3 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Windsor that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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The historical area of Windsor awaits your stay

Enjoy the history and other features of Windsor. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windsor

Are you hoping to discover attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Windsor a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Deadwood (18.6 mi / 29.9 km)
  • Sylvan Heights Waterfowl Park (28 mi / 45.1 km)
  • Roanoke Country Club (13.6 mi / 21.9 km)
  • Chowan Golf and Country Club (22.3 mi / 36 km)

Transport to and around Windsor

The nearest airport is in Greenville, NC (PGV-Pitt-Greenville), located 35 mi (56.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, North Carolina, the best area to stay is near the charming downtown district. This area offers a delightful blend of history and community spirit, making it an ideal base for your visit. You can find a variety of properties here, suiting different preferences and budgets.Staying in downtown Windsor puts you within walking distance of some of the town's top attractions. One highlight is the scenic Roanoke River, where you can enjoy leisurely strolls along the waterfront or partake in outdoor activities such as fishing and kayaking. Additionally, the historic sites, including the old courthouse and local museums, provide a fascinating glimpse into the town's rich heritage.Another lovely neighbourhood to consider is around the outskirts, which offers a more tranquil setting while still being conveniently close to downtown. Here, you'll find spacious properties with beautiful gardens, superb for families or those looking for a peaceful retreat. This area also provides easy access to local parks, where you can unwind and enjoy nature.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, the most popular types of holiday rental accommodations are cottages, holiday houses, and cabins, with several options available in the area. These rentals are often situated in serene surroundings, providing a peaceful retreat for visitors. Typically, guests can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation. Many of these properties feature charming interiors, making them ideal for family gatherings or intimate getaways.
Are there any family house rentals in Windsor?
In Windsor, North Carolina, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The homes typically feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play and enjoy the fresh air. Visitors will also appreciate amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.The town is situated near various parks and recreational areas, allowing families to engage in outdoor activities together. The local community offers a charming atmosphere, and families can explore nearby attractions that showcase the region's rich history and natural beauty.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, North Carolina, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a peaceful atmosphere, making it an ideal spot for a relaxing getaway. Many of the available rentals come with amenities such as private pools and hot tubs for unwinding after a day of exploring. Additionally, you can expect to find spacious living areas, fully equipped kitchens for self-catering, and outdoor spaces great for enjoying the warm North Carolina weather.
Are there any remote work holiday rentals in Windsor?
In Windsor, North Carolina, there are several remote work holiday rentals available, providing a convenient setting for those looking to combine work and leisure. Many of these properties are equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for work-related tasks. Additionally, you can expect features like designated desk areas in some units, making it easier to set up a productive workspace.The town itself offers a peaceful atmosphere, with nearby parks and local attractions that provide opportunities for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windsor?
In Windsor, holiday rentals often feature a range of desirable amenities to enhance guest comfort. Many properties come with kitchens, allowing travellers to prepare their own meals, while air conditioning is commonly available to ensure a pleasant indoor climate during warmer months. Additionally, many rentals include outdoor spaces such as decks or patios, superb for enjoying the fresh air. For families, some accommodations provide sofa beds and a selection of books for children, ensuring a family-friendly atmosphere.
When is the best time to visit Windsor for a holiday rental?
The best time to visit Windsor for a holiday rental is during the summer months, particularly in July, when the town comes alive with vibrant energy and warm weather. This peak season, spanning from June to August, is ideal for those looking to enjoy outdoor activities, including fishing, kayaking, and exploring local parks. The pleasant temperatures, typically ranging from around 20 to 30 degrees Celsius, create a great backdrop for leisurely strolls along the scenic waterfront.In July, you can expect a lively option, with many visitors drawn to Windsor's charming attractions and community events. This is a fantastic time to immerse yourself in the local culture, sample delicious Southern cuisine, and enjoy the welcoming spirit of the town.If you're seeking a more budget-friendly option, consider planning your visit in February. While it may be less crowded, February offers a great experience with its serene environment and opportunities for winter activities such as birdwatching and enjoying the natural beauty of the area in a quieter setting.Ultimately, your ideal time to visit Windsor will depend on your preference for lively summer adventures or a tranquil winter escape.
What are the top attractions in Windsor?
In Windsor, North Carolina, visitors can explore a range of attractions that showcase the area's rich history and natural beauty. The historic downtown area features charming architecture and local shops, great for a leisurely stroll. Nearby, the Cashie River offers opportunities for fishing, kayaking, and scenic views, making it a great spot for outdoor enthusiasts. The Windsor Museum provides insights into the town's heritage, while the surrounding countryside is ideal for exploring nature trails and taking in the serene landscape.
Are all fees included in the Windsor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windsor holiday home booking on Stayz?
To find Windsor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.