Windermere holiday homes

We found 453 holiday rentals — enter your dates for availability
Discover a selection of 14 cottages and other holiday rentals in Windermere that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and Wi-Fi. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Windermere

Showing deals for:18 Dec - 25 Dec

Kitchen
Dock
Living Room
Backyard
Wonderful
(13 reviews)

Lake Muskoka retreat! Perfect spot for family and friends.

Muskoka Lakes

8% off
NZ$16,759
for 7 nights, 1 cottage
NZ$2,394 per night
includes taxes & fees
Lake Muskoka retreat! Perfect spot for family and friends.
Property grounds
Exterior
Property grounds
Private kitchen
Exceptional
(27 reviews)

TuckAway Rustic Lakefront Cottage in Muskoka

Muskoka Lakes

8% off
NZ$4,814
for 7 nights, 1 cottage
NZ$688 per night
includes taxes & fees
TuckAway Rustic Lakefront Cottage in Muskoka
Living area
Exterior detail
Private kitchen
Interior
Exceptional
(13 reviews)

Muskoka Tiny Home

Muskoka Lakes

12% off
NZ$1,983
for 7 nights, 1 cabin
NZ$283 per night
includes taxes & fees
Muskoka Tiny Home
Second living room with fireplace!
Open concept entertaining!
Dining
Property grounds
Exceptional
(26 reviews)

Newly Renovated Secluded Cottage

Huntsville

8% off
NZ$7,134
for 7 nights, 1 cottage
NZ$1,019 per night
includes taxes & fees
Newly Renovated Secluded Cottage
Outdoor dining
Living area
Exterior
Golf
Exceptional
(10 reviews)

Private 4-Bedroom Lakeside Cottage on Nutt Lake, Muskoka

Muskoka Lakes

10% off
NZ$4,868
for 7 nights, 1 cottage
NZ$695 per night
includes taxes & fees
Private 4-Bedroom Lakeside Cottage on Nutt Lake, Muskoka
Interior
Terrace/patio
Private kitchen
Exterior
Exceptional
(16 reviews)

Lakefront Cottage for families, just minutes from Port Carling in Muskoka!

Muskoka Lakes

8% off
NZ$4,666
for 7 nights, 1 cottage
NZ$667 per night
includes taxes & fees
Lakefront Cottage for families, just minutes from Port Carling in Muskoka!
Sauna
Dining
6 person Hot tub
Mara Muskoka Waterfront Cottage
Very good
(8 reviews)

The Mara Waterfront Cottage, Muskoka

Huntsville

16% off
NZ$6,457
for 7 nights, 1 home
NZ$922 per night
includes taxes & fees
The Mara Waterfront Cottage, Muskoka
Property grounds
Exterior
Living area
Private kitchen
Exceptional
(14 reviews)

Bala Vida Cabin - Steps to Lake Muskoka w/ pond, fire pit & cedar barrel sauna ✌🏼

Muskoka Lakes

8% off
NZ$5,000
for 7 nights, 1 cottage
NZ$714 per night
includes taxes & fees
Bala Vida Cabin - Steps to Lake Muskoka w/ pond, fire pit & cedar barrel sauna ✌🏼

  • 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

Relaxing Windermere will entice you

Enjoy the history and other features of Windermere. This city is relaxing and romantic, recognised for its lake, golfing and bars. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Windermere

Are you hoping to discover attractions to see in the city? Venture out of your holiday home and experience everything that makes Windermere a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Windermere Golf & Country Club (0.1 mi / 0.1 km)
  • The Rock Golf Course (4.5 mi / 7.3 km)
  • Lake Joseph Golf Club (5.5 mi / 8.9 km)
  • Diamond In The Ruff Golf Course (5.7 mi / 9.2 km)
  • Muskoka Lakes Winery (9 mi / 14.4 km)
  • Rocky Crest Golf Club (12 mi / 19.2 km)

Exploring the natural landscape of Windermere

Whether you're an adventurous traveller or just want to appreciate the scenery, Windermere is a great place to get out in nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Rosseau (3 mi / 4.8 km)
  • Mirror Lake (4.2 mi / 6.8 km)
  • Lake Joseph (9.2 mi / 14.8 km)
  • Lake Muskoka (10 mi / 16.1 km)
  • Port Sydney Beach (13.6 mi / 21.9 km)
  • Torrance Barrens Dark-Sky Preserve (15.6 mi / 25.1 km)

Travelling to and around Windermere

The nearest airport is in Muskoka, ON (YQA), located 18.1 mi (29.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Windermere when booking a holiday rental?
When considering the best area to stay in Windermere, Ontario, a highly recommended option is the charming neighbourhood around the lake itself. This area offers a delightful blend of natural beauty and recreational activities, making it ideal for holiday rentals. Here, you can find a variety of properties that range from quaint cottages to more spacious family homes, providing ample choice for visitors.One of the top attractions in this vicinity is the stunning Lake Rosseau, which offers opportunities for swimming, kayaking, and picturesque waterfront walks. Additionally, the nearby Muskoka Lakes region is renowned for its scenic landscapes and outdoor adventures, making it superb for nature enthusiasts. The area is also close to local dining options and boutique shops, enhancing the overall holiday experience.
When is the best time to visit Windermere for a holiday rental?
The best time to visit Windermere for a holiday rental is during the peak season from June to August, when the area comes alive with outdoor enthusiasts and families seeking fun in the sun. July stands out as the most popular month, offering warm temperatures ranging from 20 to 30 degrees Celsius, superb for swimming, hiking, and enjoying the stunning natural beauty of the surrounding landscapes.During these summer months, visitors can partake in a variety of activities, including boating on the crystal-clear waters of Lake Windermere and exploring the scenic trails that wind through the lush greenery. The vibrant setting is ideal for those who enjoy socialising and making the most of the abundant sunshine.For travellers looking for a more budget-friendly option, November is a charming time to visit. While it falls outside the high tourist season, this month allows for a peaceful retreat amidst the beautiful autumn foliage. You can enjoy the tranquil surroundings and take in the spectacular views without the crowds, making it a wonderful time for those who appreciate nature's quieter moments.
What are the top attractions in Windermere?
In Windermere, Ontario, visitors can enjoy a variety of attractions that showcase the area's natural beauty and outdoor activities. The stunning Lake Rosseau, part of the Muskoka Lakes, is a major highlight, offering opportunities for boating, swimming, and fishing. Exploring the surrounding trails, such as those in the nearby Muskoka Lakes Provincial Park, provides excellent hiking routes with scenic views of the landscape.For those interested in local culture, the charming village of Windermere features quaint shops and eateries, allowing visitors to immerse themselves in the region's laid-back atmosphere. Additionally, the nearby town of Bracebridge is home to the picturesque Bracebridge Falls, which is particularly beautiful in the autumn when the foliage changes colour.Another must-visit spot is the Windermere Marina, where visitors can rent watercraft or simply enjoy the serene setting.
Are all fees included in the Windermere holiday homes prices shown on Bookabach?
Bookabach 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 Windermere holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Windermere 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 Windermere holiday homes?
You can find great discounts on holiday homes in Windermere on Bookabach, 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 Windermere holiday home booking on Bookabach?
To find Windermere holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Windermere?
A long-stay holiday home in Windermere 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 Bookabach?
Bookabach'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 Windermere holiday home?
Book your Windermere 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windermere?
Prices for holiday homes in Windermere 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. Bookabach offers something for every taste and budget, from affordable homes in Windermere to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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