Windsor, Virginia holiday accommodation: short-term house rentals & properties

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.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor

Serene 8 acre log house vacation getaway w/private hot tub and river access!

Sleeps 8 · 4 bedrooms · 2 bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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)
Lamberts Point Golf Course (24.6 mi / 39.6 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)

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

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.