Photo by Jeff White

Simcoe holiday lettings

We found 81 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Simcoe to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Simcoe

Showing deals for:14 Nov - 21 Nov

Image gallery for Amazing view, heated pool, gardens, beach, trails, wineries, shops & restaurants

Pool from balcony off of master bedroom
9.4 out of 10 rating
Exceptional
(12 reviews)

Amazing view, heated pool, gardens, beach, trails, wineries, shops & restaurants

Port Rowan, ON

11% off
Price is £1,930
£276 per night
includes taxes & fees
Amazing view, heated pool, gardens, beach, trails, wineries, shops & restaurants

Find spaces that suit your style

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Simcoe

Find out more about Simcoe

Delight in the waterfront landscape of Simcoe

Enjoy the wineries and other features of Simcoe. This city's coffee shops, horse riding and spas attract many visitors, as does its welcoming and romantic location. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Simcoe

Do you want to discover attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Simcoe has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bonnieheath Estate Lavender & Winery (4.3 mi / 6.9 km)
  • Burning Kiln Winery (10.5 mi / 16.9 km)
  • Wagon Wheel Produce & Corn Maze (4.5 mi / 7.3 km)
  • Woodside Greens Golf Club (5.3 mi / 8.5 km)
  • Villa Nova Estate Winery (7.2 mi / 11.6 km)
  • Wooden Bear L Winery (2.4 mi / 3.9 km)

Exploring the natural features in Simcoe

Whether you're looking for fun outdoor activities or just want to take in the scenery, Simcoe is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Long Point Provincial Park (18.3 mi / 29.4 km)
  • Long Point Beach (18.4 mi / 29.6 km)
  • Long Point National Wildlife Area (19.3 mi / 31 km)
  • Waterford North Conservation Area (6.6 mi / 10.7 km)
  • Whistling Gardens (11.2 mi / 18 km)
  • Hay Creek Conservation Area (4.7 mi / 7.6 km)

Transport options to and around Simcoe

The nearest airport is in Hamilton, ON (YHM-John C. Munro Hamilton Intl.), located 29.5 mi (47.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Simcoe when booking a holiday rental?
When considering a holiday rental in Simcoe, Ontario, a fantastic area to stay in is the downtown district. This vibrant neighbourhood offers a delightful mix of local shops, restaurants, and cultural attractions, making it a superb base for exploring the town. You'll find a variety of properties available, suiting different preferences and budgets, ensuring that visitors can find something that suits their needs.

One of the top attractions nearby is the Norfolk County Fair and Horse Show, which takes place annually and celebrates the region's agricultural heritage with lively events and exhibits. Additionally, the charming Simcoe Town Centre is just a short walk away, where you can enjoy unique shops and cafes. The proximity to beautiful parks, like the nearby Waterford Heritage Trail, offers excellent opportunities for outdoor activities such as walking, cycling, and enjoying nature.
How much does it cost to rent a holiday home in Simcoe?
Prices for holiday rentals in Simcoe 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simcoe to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Simcoe holiday house rentals?
You can find great discounts on house rentals in Simcoe 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.
Can I find long-stay holiday rentals in Simcoe?
A long-stay holiday rental in Simcoe 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 Simcoe holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Simcoe 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.
What are popular rental amenities in Simcoe?
In Simcoe, the holiday rental market offers a variety of accommodations, although specific amenities are not prominently highlighted. Visitors can expect basic comforts in many properties, such as kitchens for self-catering, comfortable living areas for relaxation, and essential furnishings. The town's proximity to natural attractions may lead to rentals that provide outdoor spaces or easy access to local parks and recreational areas.
When is the best time to visit Simcoe for a holiday rental?
July marks the peak season for visiting Simcoe, Ontario, when the town comes alive with vibrant summer activities. This month is particularly popular among families and outdoor enthusiasts who flock to the area to enjoy the warm weather and access to stunning natural landscapes, including lakes and parks great for picnicking, hiking, and water sports.

From July through September, Simcoe offers a wealth of opportunities for sightseeing and outdoor adventures. You can explore the scenic trails, partake in local festivals, or simply relax by the waterfront. The temperatures during this period typically range from the mid-teens to low 20s Celsius, making it comfortable for a variety of outdoor activities.

If you're looking for a more budget-friendly option, consider planning your visit in November. While the summer crowds have dispersed, you can still enjoy the serene beauty of the area, with opportunities for quiet walks and enjoying the crisp autumn air. Plus, the fall scenery can be quite picturesque, providing a peaceful retreat from the busyness of the summer months.
How early should I book a Simcoe holiday rental?
Book your Simcoe holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Simcoe home rental booking on Vrbo?
To find Simcoe holiday 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 Simcoe holiday 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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