Windsor vacation rentals

We found 14 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Windsor that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and WiFi. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.
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Find out more about Windsor

Find out more about Windsor

Why visit Windsor

  1. Historic Attractions: Explore fascinating history museums and historic colleges that reflect Windsor's rich heritage.
  2. Scenic Riverfront: Stroll along the beautiful Windsor Riverfront, enjoying scenic views and the welcoming atmosphere.
  3. Outdoor Adventures: Experience a variety of outdoor activities, including beach outings and nature exploration.
  4. Charming Downtown: Discover the quaint downtown area filled with friendly locals, shops, and unique experiences.
  5. Diverse Accommodation: Choose from a range of vacation rentals, from cozy apartments to charming cottages.

Popular types of accommodation in Windsor

Discover the charm of Windsor with our diverse vacation rentals. Whether you're seeking a cozy apartment, a spacious private vacation home, or a charming cottage, we have options to suit every preference. Our Windsor rentals provide the perfect home base to explore the city’s attractions and enjoy local experiences. With transparency and savings at the forefront, you can relax knowing you’ve made the right choice for your getaway.

  • Apartments: The top choice for holiday stays in Windsor, offering modern amenities and convenient locations.
  • Houses: Ideal for families or groups seeking spacious and comfortable living with a home-like atmosphere.
  • Cottages: A charming option that provides a cozy retreat, often nestled in picturesque surroundings.
  • Cabins: Perfect for those wanting a rustic experience, bringing you closer to nature.
  • Chalets: A delightful option that combines comfort and unique architectural style, often located near scenic vistas.**

Top attractions in Windsor

Windsor, Nova Scotia, offers a delightful mix of attractions for family, business, and city-themed vacations. Visitors can explore beautiful lakes, fascinating history museums, and historic colleges and universities. With options for outdoor adventures, beach outings, and romantic experiences, Windsor caters to a variety of travellers seeking to create memorable moments in this charming town.

  1. Haliburton House Museum: Explore this charming historical museum showcasing the life and times of Nova Scotia's past. The house is filled with period furnishings and offers cultural insights into the local heritage.
  2. Windsor Hockey Heritage Centre: Celebrate Canada's beloved sport at this interactive sports museum. It features memorabilia and exhibits that highlight Windsor's rich hockey history, combining sports enthusiasm with cultural significance.
  3. Trecothic Creek and Windsor Railway: Experience the unique blend of culture and history at this museum, where you can learn about early railway operations and enjoy scenic views along the picturesque creek.

Things to do recommended for couples

Windsor, Nova Scotia offers a perfect romantic getaway. Enjoy skiing at Ski Martock, just 6.4km away, or indulge in wine tasting at Avondale Sky Winery, 3.2km from town. For a more intimate experience, visit Luckett Vineyards, located 16.1km away, for charming entertainment and romance.

Things to do recommended for families

Families visiting Windsor, Nova Scotia, can enjoy a day of wellness and relaxation at Reservoir Park, located 13.2km away, or explore Lockhart and Ryan Memorial Park, just 25.7km from town. Both parks offer recreational activities perfect for a family outing.

Things to do recommended for groups

Groups visiting Windsor, Nova Scotia can enjoy a captivating performance at the Mermaid Theatre, hit the greens at the Avon Valley Golf and Country Club, or embark on an exhilarating adventure at Ontree Fun and Adventure Park, featuring zip lines and rope courses for outdoor thrills.

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

When planning your trip—whether you’re travelling with friends, family, pets, or seeking extended accommodations—be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Windsor with young kids: Travelling with young children can present its challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Windsor: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windsor

Windsor, Nova Scotia, offers a delightful blend of family-friendly and culturally rich experiences. Stroll through the charming downtown, where friendly locals welcome you amidst scenic views along the Windsor Riverfront. With outdoor adventures and cultural attractions just a short walk away, you'll discover the perfect setting for a memorable vacation. Explore detached homes that reflect the city's heritage, making Windsor an ideal destination for both relaxation and exploration.

  • Falmouth: Falmouth is a charming city located a mere 3.2km from Windsor. Known for its family-friendly atmosphere and vibrant business community, Falmouth is a great destination for shopping enthusiasts and golf lovers alike. Visitors can explore the local shopping centres and malls, while enjoying access to beautiful urban parks, a marina, and sandy beaches. The combination of leisure and recreation makes Falmouth a perfect spot for those looking to unwind and connect with nature.
  • Martock: Situated 4.8km from Windsor, Martock is an exciting city that attracts adventure seekers and sports enthusiasts. Known for its thrilling ski fields and private country clubs, Martock offers a range of outdoor activities year-round. Visitors can enjoy skiing in the winter months or relax on the beautiful family-friendly beaches during warmer seasons. With urban parks nearby, it’s the ideal locale for those looking to balance sports and relaxation.
  • Avondale: Located 3.2km away from Windsor, Avondale is a picturesque city that emphasizes outdoor adventures and sports. Here, visitors can tee off at local golf courses or explore vibrant markets. The area boasts stunning natural attractions, including a national park and a historic college university, offering a rich cultural experience. With plenty of outdoor activities to engage in, Avondale is a must-visit for nature lovers and adventure seekers alike.

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 August. Peak season runs from July to September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverageAverage
April40.3°F (4.6°C)Light RainMostly CloudyAverageAverage
May48.4°F (9.1°C)Light RainMostly CloudyAverageSlightly Low
June56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
July64.8°F (18.2°C)Light RainMostly SunnySlightly HighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighSlightly High
October52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
November43.0°F (6.1°C)Light RainMostly CloudySlightly LowAverage
December34.9°F (1.6°C)Light RainMostly CloudySlightly LowSlightly Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay frequently results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a helpful platform for planning your travels, allowing you to create new trips, keep your plans on track, or review and manage your bookings. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, feel free to visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Friendly Windsor will entice you

Enjoy the area's architecture, museums and festivals and make a vacation rental your home during your stay in Windsor. This welcoming and scenic city entices travelers with its riverfront and entertainment. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Windsor

Are you searching for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes Windsor a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ski Martock (4.4 mi / 7.1 km)
  • Luckett Vineyards (9.8 mi / 15.8 km)
  • L'Acadie Vineyards (11.2 mi / 18.1 km)
  • Gaspereau Vineyards (12.3 mi / 19.8 km)
  • Ken-Wo Golf Club (15.6 mi / 25 km)
  • Fox Hill Cheese House (15.6 mi / 25.2 km)

Exploring the natural landscape of Windsor

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Windsor is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Falls Lake Provincial Park (11.4 mi / 18.4 km)
  • Lower Salter Lake (12.1 mi / 19.5 km)
  • Robie Tufts Nature Centre (13.3 mi / 21.5 km)
  • Little Otter Lake (15.3 mi / 24.7 km)
  • Lockhart and Ryan Memorial Park (16 mi / 25.8 km)
  • Bear Lake (16.8 mi / 27 km)

Transportation to and around Windsor

The nearest airport is in Stanfield Intl. Airport (YHZ), located 30.9 mi (49.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Windsor when booking a vacation rental?
When considering a vacation rental in Windsor, Nova Scotia, the best area to stay is the historic downtown district. This charming neighbourhood is known for its picturesque streets, quaint shops, and delightful eateries, making it an ideal base for exploring the local culture. One of the top attractions in this area is the Windsor Hockey Heritage Centre, which celebrates the town's rich ice hockey history and is a must-visit for sports enthusiasts. Additionally, the scenic waterfront along the Avon River offers lovely walking paths and stunning views, superb for a leisurely stroll or a picnic.

Another great option is the area surrounding the famous Avon Valley, which boasts several vacation rentals with a more rural feel. This region is known for its beautiful landscapes and outdoor activities, providing a tranquil escape while still being close to the town centre. The nearby Cape Blomidon Provincial Park is a fantastic spot for hiking and offers breathtaking views of the Bay of Fundy, making it a popular destination for nature lovers.
How much does it cost to rent a vacation home in Windsor?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes.
Are there any discounts for Windsor vacation house rentals?
You can find great discounts on house rentals in Windsor on Vrbo, 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.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, apartments are the most popular type of vacation rental, with several available throughout the town. These apartments typically feature fully equipped kitchens, comfortable living areas, and modern amenities, making them an ideal choice for travellers seeking a home-like experience. Many are located in convenient areas close to local attractions, such as the scenic waterfront and nearby parks.
Can I find long-stay vacation rentals in Windsor?
A long-stay vacation rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work vacation rentals in Windsor?
In Windsor, Nova Scotia, there are several remote work vacation rentals available, making it an ideal spot for those looking to blend work and leisure. The town offers a peaceful environment with amenities that cater to remote workers, including properties featuring dedicated office spaces, high-speed internet, and comfortable workstations. Many rentals also provide essentials such as fully equipped kitchens and spacious living areas, allowing for a pleasant stay while maintaining productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 on Vrbo 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.
When is the best time to visit Windsor for a vacation rental?
September is the most popular time to visit Windsor, Nova Scotia, as it marks the transition from the vibrant summer season to the beautiful autumn months. During the peak season from July to September, visitors flock to this charming town to experience its stunning landscapes and a variety of outdoor activities, including hiking and cycling along the scenic trails.

The weather in September is typically mild, with temperatures ranging from 15 to 20 degrees Celsius, making it an ideal time for sightseeing and enjoying the local attractions. You can wander through the picturesque streets, explore the historic sites, or take in the breathtaking views of the Bay of Fundy, all while experiencing the comfort of pleasant temperatures.

If you're looking for a more budget-friendly option, consider visiting Windsor in December. While this month may have fewer tourists, it offers a unique charm with winter festivities and a quieter atmosphere, superb for those who enjoy a peaceful getaway.
How early should I book a Windsor vacation rental?
Book your Windsor vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor?
In Windsor, Nova Scotia, visitors can explore several popular attractions that highlight the area's rich history and natural beauty. The town is renowned for its connection to the Annapolis Valley, making it a great base for discovering the scenic landscapes and vineyards of the region.

The historic downtown area of Windsor features charming architecture and local shops, while the nearby Avon River offers beautiful views and opportunities for kayaking and canoeing. The Windsor Railway Museum is another highlight, showcasing the town's railway history and providing insight into its development.

Just a short drive away, visitors can enjoy the stunning landscapes of Cape Blomidon Provincial Park, which offers breathtaking views of the Bay of Fundy and its impressive tides. Additionally, the nearby Grand Pré National Historic Site commemorates the Acadian heritage and is a UNESCO World Heritage Site, making it a must-visit for history enthusiasts.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windsor vacation rental prices shown on Vrbo?
Vrbo 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.
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