Windermere holiday lettings

We found 320 holiday rentals — enter your dates for availability
Discover a selection of 15 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:6 Nov - 13 Nov

Private kitchen
Exterior
Living area
Property grounds
Exceptional
(27 reviews)

TuckAway Rustic Lakefront Cottage in Muskoka

Muskoka Lakes

8% off
£2,062
for 7 nights, 1 cottage
£295 per night
includes taxes & fees
TuckAway Rustic Lakefront Cottage in Muskoka
Outdoor dining
Living area
Exterior
Living area
Exceptional
(6 reviews)

Private 4-Bedroom Lakeside Cottage on Nutt Lake, Muskoka

Muskoka Lakes

10% off
£2,060
for 7 nights, 1 cottage
£294 per night
includes taxes & fees
Private 4-Bedroom Lakeside Cottage on Nutt Lake, Muskoka
Exterior
Exterior detail
Interior
Living area
Exceptional
(6 reviews)

Muskoka Tiny Home

Muskoka Lakes

12% off
£844
for 7 nights, 1 cabin
£121 per night
includes taxes & fees
Muskoka Tiny Home
Private kitchen
Terrace/patio
Exterior
Interior
Exceptional
(15 reviews)

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

Muskoka Lakes

8% off
£2,000
for 7 nights, 1 cottage
£286 per night
includes taxes & fees
Lakefront Cottage for families, just minutes from Port Carling in Muskoka!
Second living room with fireplace!
Open concept entertaining!
Property grounds
Dining
Exceptional
(25 reviews)

Newly Renovated Secluded Cottage

Huntsville

7% off
£2,238
for 7 nights, 1 cottage
£320 per night
includes taxes & fees
Newly Renovated Secluded Cottage
Modern kitchen with stainless steel appliances, double sink and dishwasher
View of lake and large deck from stairs to 2nd floor
Open concept, warm and inviting living space
2 story lake view with tons of natural light
Exceptional
(6 reviews)

Classic Muskoka Getaway - Hot Tub, Private Beach, Firepit & View!

Muskoka Lakes

8% off
£1,869
for 7 nights, 1 cottage
£267 per night
includes taxes & fees
Classic Muskoka Getaway - Hot Tub, Private Beach, Firepit & View!
Property grounds
Exterior
Living area
Private kitchen
Exceptional
(12 reviews)

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

Muskoka Lakes

7% off
£1,953
for 7 nights, 1 cottage
£279 per night
includes taxes & fees
Bala Vida Cabin - Steps to Lake Muskoka w/ pond, fire pit & cedar barrel sauna ✌🏼

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Why visit Windermere

  • Scenic Lakeside Views: Enjoy the breathtaking vistas of the picturesque lakes, perfect for a relaxing retreat.
  • Windermere Jetty Museum: Discover local history and maritime heritage at this engaging museum.
  • Outdoor Adventures: Explore numerous trails and engage in activities like hiking, boating, and fishing.
  • Charming Accommodations: Stay in delightful cottages and lakeside retreats that enhance your holiday experience.
  • Windermere Peaks: Take in stunning views and immerse yourself in the natural beauty of the region.

Popular types of accommodation in Windermere

Planning a getaway to Windermere? You're in for a treat! Explore a delightful selection of holiday cottages, houses, and condos that cater to all your accommodation needs. Whether you’re searching for charming cottages in Windermere or lakeside retreats near Lake Windermere, our platform offers transparent information and great savings. Discover your ideal holiday rental in Windermere today and make your stay truly memorable.

  • Cottages: The most sought-after option for vacation stays in Windermere, offering a charming and homely escape amidst nature.
  • Houses: A fantastic choice for larger groups or families, providing spacious living areas and a sense of privacy.
  • Condos: A convenient and modern accommodation type, ideal for those who prefer a blend of comfort and accessibility.
  • Chalets: A delightful option with a rustic charm, perfect for enjoying the scenic surroundings.
  • Cabins: A popular choice for a cosy, woodland retreat, allowing guests to immerse themselves in the tranquil outdoors.**

Top attractions in and around Windermere

Windermere, nestled in the stunning Muskoka Lakes, is perfect for a romantic getaway or an outdoor adventure. Visitors can enjoy the picturesque lakes, explore local attractions such as the Windermere Jetty Museum, wander along the piers, and take in the breathtaking views from Windermere Peaks. This charming destination offers a delightful blend of natural beauty and engaging activities for an unforgettable holiday experience.

  • Lake Muskoka: A stunning lake located 6.2km from Windermere, Lake Muskoka offers picturesque beaches and breathtaking scenery, perfect for outdoor activities and romantic escapades.
  • Windermere Marina: Nestled within Windermere, this marina provides a thrilling adventure with opportunities for water sports, relaxing beach time, and a vibrant outdoor atmosphere.
  • Windermere Golf & Country Club: Situated in Windermere, this family-friendly golf course offers a relaxing environment, ideal for unwinding while enjoying a round of golf amidst beautiful landscapes.

Things to do recommended for couples

For a romantic getaway in Windermere, indulge in the Muskoka Lakes Winery, a charming spot just 5.6km away, perfect for wine tasting. Alternatively, embrace adventure at Muskoka Sports and Recreation, only 3.1km away, where you can enjoy thrilling water sports together in stunning surroundings.

Things to do recommended for families

Families visiting Windermere can have a splashing good time at High Falls Water Park, located 8.1km away. With its thrilling water slides and family-friendly atmosphere, it's perfect for creating unforgettable memories together.

Things to do recommended for groups

In Windermere, groups can enjoy a round of golf at Lake Joseph Golf Club, indulge in a tasting at Muskoka Brewery, and experience a captivating performance at Gravenhurst Opera House, all while soaking in the picturesque scenery of Muskoka Lakes.

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

When travelling with a group, family, pets, or seeking extended stays, it's important to filter according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windermere with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for socialising with your group. Luckily, you can easily apply filters for all of this and more on Vrbo.
  • Traveling to Windermere with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, as well as access to 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 Windermere: For many, a family holiday wouldn’t be the same without their beloved pet. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations supply feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windermere: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to consider including amenities like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Windermere

Windermere, a charming village in Muskoka Lakes, is perfect for a romantic getaway or a relaxing family holiday. Explore scenic cottages that offer breathtaking views, immerse yourself in the natural beauty of Windermere, and stroll through the quaint town. Indulge in peaceful adventures and discover the area's rich history, making it a secluded retreat for those seeking both relaxation and adventure. Windermere truly encapsulates the essence of a picturesque Canadian escape.

  • Muskoka Lakes: Nestled a mere 249m from Windermere, Muskoka Lakes is a picturesque city renowned for its stunning natural beauty and outdoor activities. Visitors flock here for a romantic experience amid scenic landscapes that include tranquil lakes and lush parks. The area offers a variety of attractions, such as golf courses and ski resorts, providing ample opportunities for relaxation and adventure. Notable landmarks include the nearby national state park, perfect for hiking and exploring, ensuring a memorable getaway for nature lovers.
  • Port Carling: Located 2.5km from Windermere, Port Carling is a charming village that boasts a rich tapestry of outdoor experiences and breathtaking scenery. This destination is particularly popular among couples seeking a romantic escape. Guests can indulge in activities at local golf courses or unwind at luxurious resorts. The village’s proximity to beautiful lakes and national parks enhances its appeal, making it an ideal spot for leisurely strolls and picnics amid nature's splendour.
  • Minett: Just 3.1km from Windermere, Minett is a quaint village known for its idyllic outdoor surroundings and scenic vistas. Ideal for those seeking romance and adventure, Minett offers a range of activities, including golf, skiing, and visits to local resorts. The area is home to stunning lakes and a nearby theme park, providing entertainment for families and couples alike. With its charming atmosphere and abundance of natural beauty, Minett is a delightful addition to your Muskoka Lakes itinerary.

Best time to go to Windermere

If you're planning a trip to Windermere, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January16.7°F (-8.5°C)Light RainVery CloudyAverageAverage
February17.8°F (-7.9°C)Light RainVery CloudyAverageSlightly Low
March27.5°F (-2.5°C)Light RainMostly CloudyAverageSlightly Low
April39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
May53.6°F (12.0°C)Light RainMostly SunnyAverageAverage
June61.7°F (16.5°C)Light RainMostly SunnyModerately HighSlightly High
July67.5°F (19.7°C)Light RainMostly SunnyModerately HighSlightly High
August66.0°F (18.9°C)Light RainMostly SunnyModerately HighSlightly High
September59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
October47.5°F (8.6°C)Light RainMostly CloudyModerately LowAverage
November35.4°F (1.9°C)Light RainMostly CloudyModerately LowAverage
December25.3°F (-3.7°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you keen to save on your upcoming holiday? Being flexible with your travel dates can make a substantial difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of accommodation.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous ones, or review and arrange your travel plans. Here, you can easily find any properties you've saved or booked, thoughtfully organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • High Lake (5.4 mi / 8.7 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.
How much does it cost to rent a holiday home in Windermere?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windermere 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 Windermere holiday house rentals?
You can find great discounts on house rentals in Windermere 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 Windermere?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Windermere holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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 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.
How early should I book a Windermere holiday rental?
Book your Windermere 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.
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.
Can I change or cancel my Windermere home rental booking on Vrbo?
To find Windermere 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windermere 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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