Windsor holiday rentals

We found 4 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and air conditioning. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Windsor

  • Scenic natural beauty: Windsor offers tranquil parks and natural settings perfect for leisurely walks and family outings.
  • Charming cultural mix: Embrace the blend of local arts and cultural experiences in community centres and quaint urban spots.
  • Family-friendly attractions: Enjoy cosy parks and picturesque surroundings ideal for both romantic getaways and family holidays.
  • Local shopping delights: Discover unique local shops that add to Windsor’s quaint, charming character.
  • Versatile accommodation: Experience a range of generic lodging options including private homes, condos, and cottages.

Popular types of accommodation in Windsor

Discover Windsor, Virginia, a charming city offering delightful attractions and experiences. Explore the scenic beauty, historic landmarks and cosy parks that define its character. If you are unsure what type of accommodation you can expect in Windsor, we have you covered with popular options such as Private Holiday Homes, Condos, and Cottages. Enjoy transparent, customer-centred holiday rentals in Windsor, ensuring a memorable stay in this vibrant locale.

  • Private Holiday Homes: These spacious and comfortable residences are the top choice for visitors seeking a home-away-from-home experience in Windsor.
  • Condos: Often featuring modern amenities, condos provide a convenient and stylish option for those looking to enjoy a more communal living space.
  • Cottages: Quaint and charming, cottages offer a picturesque retreat, perfect for a relaxing getaway amidst beautiful surroundings.
  • Apartments: Ideal for shorter stays, apartments deliver a practical and flexible accommodation choice, catering to various group sizes.
  • Villas: Luxurious and spacious, villas are perfect for those seeking an upscale experience with ample room for relaxation and entertainment.**

Top attractions near Windsor

Windsor, Virginia, offers a charming escape for outdoor enthusiasts and families alike. Visitors can explore urban parks and engage with local arts at community centres while enjoying the tranquil atmosphere. This quaint town provides a blend of cultural experiences and natural beauty, making it an ideal destination for romantic getaways or family holidays. Embrace the local charm and discover the hidden gems that Windsor has to offer.

  • Bacons Castle: Experience a romantic culture-rich castle 32km away, embodying historic allure and mystery.
  • Lake Prince: Enjoy scenic outdoor adventures at a beach lake 11km away, perfect for a leisurely day in nature.
  • Suffolk Center for Cultural Arts: Immerse yourself in local cultural expressions at an arts centre 18km away, celebrating artistic endeavours.

Things to do recommended for couples

Windsor offers a charming escape for couples. Enjoy a leisurely stroll through scenic parks, indulge in a candlelit dinner at a local bistro, or take a romantic boat ride on the nearby rivers, soaking in the picturesque views and tranquil atmosphere together.

Things to do recommended for families

Families visiting Windsor can enjoy a fun day at the local park, explore the interactive exhibits at the Windsor Science Centre, and experience hands-on activities at the community centre for a memorable family outing.

Things to do recommended for groups

Groups visiting Windsor can immerse themselves in local history at the charming Windsor Castle, partake in a guided tour of the quaint town, and enjoy a relaxing picnic at the scenic waterfront. Don't miss the chance to explore the nearby natural trails for a delightful walk.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windsor

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to filter your search using the appropriate priorities. Here are a few Stayz booking tips for you.

  • Traveling to Windsor with a group: Consider how many bedrooms you require, as well as facilities like a fully-equipped kitchen or an outdoor area suitable for a group get-together. Fortunately, you can refine your search for these features, and many others, on Stayz.
  • Traveling to Windsor with young kids: Travelling with young children can present its difficulties. It’s essential to prioritise their comfort and safety, alongside suitable amenities for their age, such as a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Windsor: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're after holiday lets offering discounts for long-term stays, you've come to the right place. With the appropriate filter, you can effortlessly find and save on monthly lets. You might also consider including a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay near Windsor

Explore the charm of Windsor, Virginia, where natural features and local shops create a delightful escape. Enjoy family-friendly excursions and romantic walks amid scenic surroundings. The city offers a great location for those seeking a relaxing and engaging holiday experience, with a mix of business and leisure atmospheres to suit all tastes.

  • Suffolk: Suffolk is a vibrant city located 18km from Windsor. It offers a variety of experiences, from family outings to romantic adventures, set against a backdrop of well-loved outdoor spaces. Visitors can enjoy a pleasant stroll along the boardwalk, indulge in some shopping at the bustling centre and mall, and then explore the local attractions including a tourist precinct, an esplanade and a nearby beach. The city’s blend of urban charm and scenic beauty makes it an appealing destination for travellers seeking a diverse holiday experience.
  • Great Dismal Swamp National Wildlife Refuge: This natural haven, characterised by its water features and park-like setting, is situated 29km from Windsor. It is a magnet for those in search of outdoor adventures, captivating scenery, and a touch of thrill. The Refuge offers a rich tapestry of activities including leisurely walks along boardwalks, invigorating hikes on dedicated trails, and exploration within its recreational areas. Attractions such as a picturesque lake, a serene nature reserve and an inviting esplanade further enhance the experience, making it a perfect retreat for nature enthusiasts.
  • Rushmere: Rushmere is a charming village located 31km from Windsor and is ideal for those seeking a blend of outdoor activities, family fun and scenic beauty. The village boasts accessible recreational areas and bustling shopping centres, providing ample opportunities for leisurely exploration. Local attractions include a welcoming beach, a delightful park and a national state park, all of which offer a glimpse into the area’s natural splendour and community spirit.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.1°F (4.5°C)Light RainMostly SunnyLowSlightly Low
February43.5°F (6.4°C)Light RainMostly SunnyAverageSlightly Low
March49.5°F (9.7°C)Light RainMostly SunnyAverageSlightly Low
April59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
May67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
June75.0°F (23.9°C)Light RainMostly SunnyHighSlightly High
July79.2°F (26.2°C)Light RainMostly SunnyHighSlightly High
August77.5°F (25.3°C)Light RainMostly SunnyAverageSlightly High
September72.5°F (22.5°C)Light RainMostly SunnyHighAverage
October62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
November51.6°F (10.9°C)Light RainMostly SunnyLowAverage
December45.3°F (7.4°C)Light RainMostly SunnyLowAverage

Booking with Stayz is a breeze

Are you aiming to reduce costs on your upcoming journey? Consider embracing some flexibility with your travel dates, as prices can vary. Moreover, choosing an extended stay often leads to significant savings. To locate the ideal Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz's innovative Trip Board offers you a dedicated space to plan new journeys, pick up right where you left off, or organise your travel arrangements. You can easily access properties you've saved or booked, now categorised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Windsor

Are you searching for attractions to see in the city? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Riverfront Golf Club (17.5 mi / 28.2 km)
  • Serendipity Meadworks (11.5 mi / 18.5 km)
  • Cypress Creek Golfers’ Club (12.3 mi / 19.8 km)
  • Smithfield Winery (13.5 mi / 21.7 km)
  • The Peanut Patch (17.7 mi / 28.5 km)
  • Bounce House (24.8 mi / 40 km)

Exploring the natural features in Windsor

Whether you're an active traveller or just want to take in the scenery, Windsor is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Portsmouth City Park (21.1 mi / 34 km)
  • Huntington Beach (21.5 mi / 34.6 km)
  • Lake Prince (5.8 mi / 9.3 km)
  • Windsor Castle Park (13.3 mi / 21.3 km)
  • Sandy Bottom Nature Park (24.7 mi / 39.8 km)
  • Camptown Park (12.2 mi / 19.7 km)

Transport options to and around Windsor

The nearest airport is in Newport News, VA (PHF-Newport News - Williamsburg Intl.), located 26.3 mi (42.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Norfolk, VA (ORF-Norfolk Intl.), which is 30.7 mi (49.5 km) away.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, Virginia, the most appealing area to stay in would be the charming outskirts of the town, particularly near the historic sites and natural beauty that the region has to offer. One top neighbourhood is the area surrounding the Blackwater River, where visitors can enjoy scenic walks and the tranquil atmosphere that the river provides. This locale is superb for those who appreciate outdoor activities, as it offers opportunities for fishing, kayaking, and nature trails.Another attractive option is the vicinity close to the Virginia State University, which adds a vibrant energy to the area with its cultural events and community activities. Staying near this educational institution also allows easy access to the local art scene and the various festivals that are celebrated throughout the year.Although the exact number of holiday rentals in Windsor can vary, there are several properties available that cater to different preferences, from quaint cottages to more spacious houses, ensuring that visitors can find accommodation suited to their needs.
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 peak season from May to July, particularly in June, when the town is alive with activity and charm. This vibrant period attracts tourists eager to enjoy the warm weather and partake in various outdoor events and festivals, making it an ideal choice for those who appreciate a lively option.June sees comfortable temperatures ranging from 15 to 30 degrees Celsius, great for exploring Windsor's scenic parks or taking leisurely strolls along the picturesque waterfront. The beautiful landscapes and blooming gardens during this time create a delightful setting for outdoor adventures and sightseeing.For travellers looking for a more budget-friendly option, December can be a lovely time to visit as well. While it falls into the low season, you can experience the tranquil beauty of Windsor during the winter months, with fewer crowds and a chance to enjoy the holiday decorations around town.Ultimately, the best time for you to book a holiday rental in Windsor will depend on whether you prefer the bustling energy of summer or the quieter, more contemplative atmosphere of winter.
What are the top attractions in Windsor?
In Windsor, Virginia, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The charming town is close to the scenic James River, where outdoor enthusiasts can enjoy activities like fishing and kayaking. The nearby historic town of Smithfield, known for its well-preserved 18th-century architecture and the famous Smithfield Historic District, offers a delightful day trip with quaint shops and local eateries.For those interested in wildlife, the Great Dismal Swamp National Wildlife Refuge is a short drive away, providing an opportunity for hiking, bird watching, and exploring the unique ecosystem. Additionally, Windsor's close proximity to larger towns like Suffolk offers access to more extensive shopping, dining, and cultural experiences.
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.

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