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)
  • Sandy Bottom Nature Park (24.7 mi / 39.8 km)
  • Lake Prince (5.8 mi / 9.3 km)
  • Windsor Castle Park (13.3 mi / 21.3 km)
  • King-Lincoln Park (21.6 mi / 34.8 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

How much does it cost to rent a holiday home in Windsor?
Several things can determine how much you pay for a holiday home in Windsor, such as the length of stay, type of property and season. But, all Stayz homes have one thing in common — exceptional value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Windsor?
The average price for a holiday home by the beach in Windsor depends on when you'll be there and the style and size of property you're searching for. You can quickly and easily find prices on Stayz by entering your destination and preferred travel dates. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
What are the top attractions for families in Windsor?
Boredom doesn't stand a chance during your Windsor holiday with these family-friendly attractions:

  • Lake Prince
  • Boykins Tavern

How old do you have to be to rent a holiday home in Windsor?
The minimum age allowed can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Windsor you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Windsor for?
The amount of time you can stay in a Windsor holiday home for is down to the property. Just put in your dates of travel to see available options offering longer term stays. They have all you need to make your extended break more comfortable and enjoyable, like kitchens and yards. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stay even longer for less.