Search Holiday Rentals in Windermere

Save an average of 15% on thousands of properties with Expedia Rewards

Become a member for free and get more than just a booking discount. Members also earn points towards their next trip.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5

Top Holiday Rentals in Windermere

Exterior
Touchstone Resort
4.0 star property
8.6 out of 10, Excellent, (222)
"Excellent place "
The price is £108
includes taxes & fees
16 May - 17 May
Touchstone Resort
Property grounds
Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka
10.0 out of 10, Exceptional, (22)
"Our family had such a special time together at the Falcon's Nest. The house was immaculate, there were special touches across the home, lovely soaps, chocolates, and the most incredible charcuterie board we've ever seen! Preet was so attentive to all of our needs, and we couldn't have asked for a better visit. Thank you!"
Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka
Lake
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
9.4 out of 10, Exceptional, (13)
"Wonderful vac..beautiful view and the cottage was perfect for us!"
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
260 feet of South West lakefront on Lake Joseph with all day sun
8.8 out of 10, Excellent, (3)
"My husband and I and another couple had a great holiday in the Muskokas. Our host, Loren was easy to communicate with and very helpful. The cottage was spacious, clean and well equipped. The bedrooms were very comfortable. We especially liked the boat dock with bunky across the road from the cottage. We had easy access to all three of lakes. Port Carling and Port Sandfield was close with lots of amenities. The pictures are accurate of what the cottage looks like. We would rent this place again...
260 feet of South West lakefront on Lake Joseph with all day sun
Property grounds
Brand new cottage on 3-Mile Lake in the heart of Muskoka
9.8 out of 10, Exceptional, (77)
"Beautiful location. The cottage was very clean and super comfortable. The kitchen was well equipped. The communication was excellent and the response to a utility issue was also excellent. We had an excellent weekend. Thanks Dave"
Brand new cottage on 3-Mile Lake in the heart of Muskoka
BBQ/picnic Area
Muskoka Lake Cottages
3.0 star property
7.2 out of 10, Good, (31)
"Muskoka Lake Cottages is a nice cabin style cottage. This cabin style cottage has a beautiful lake view of Brandy Lake that is 7mins to Port Carling and 15min to Bracebridge. Lots of fishing everywhere you can use the resort kayaks to cruise the lake that is included. Excellent stay we will be back in the near future. "
The price is £132
includes taxes & fees
14 May - 15 May
Muskoka Lake Cottages
Beach
Cozy Cottage in Muskoka
7.6 out of 10, Good, (5)
"We loved staying at the little cottage! Perfect for 2 adults, 2 kids and a dog. The fenced in yard was amazing for security of our dog as the road is very busy. The listing should say it provides a clothes drying rack, not a clothes dryer as we expected access to an electric one. With 2 girls attending wake surf camp 5 days straight it was challenging to get the towels dry. Excellent location close to all 3 lakes and shopping."
The price is £245
includes taxes & fees
7 May - 8 May
Cozy Cottage in Muskoka
Fridge, microwave, oven, stovetop
Lakefront 4-bdrm house for rent in the heart of Muskoka
9.8 out of 10, Exceptional, (6)
"We had such a great time, the place was nice and clean, the host replies as soon as they can, very communicative and easy! very quiet, there is a firepit at the back, we brought marshmallows and crackers to make smores. Few issues we have encountered that would improve our stay: was the kitchen didn't have any aluminum foils even tho basics were listed and all the groceries were closed at that time unfortunately but we survived the night with other food we've brought. Another was believed to be...
The price is £401
includes taxes & fees
14 May - 15 May
Lakefront 4-bdrm house for rent in the heart of Muskoka
Outdoor dining
Tranquil Waterfront Getaway
7.4 out of 10, Good, (6)
"We stayed with a group of friends and our kids (6 adults, 4 kids). The cottage was clean and well equipped. It's on the Muskoka river and swimming off the dock was a highlight for everyone. The hosts were responsive and helpful for the few questions we had. The only issue we encountered was that the cottage does not have great water pressure, which was challenging from the perspective of having showers, doing dishes, and getting baths organized for the kids. I asked the host about this, and his...
Tranquil Waterfront Getaway
Property grounds
Cozy Lakefront Cottage
9.6 out of 10, Exceptional, (9)
"Fell in love with this cottage from the moment we arrived. The setting is beautiful. The cottage itself is lovely and well maintained. It was comfortable and welcoming. Bianca was a wonderful host. Throughout the entire process she was available and helpful. Bianca was a pleasure to work with. We hated to leave. We look forward to returning again soon."
Cozy Lakefront Cottage
Exterior
Lakefront Muskoka Beautiful Cottage
9.0 out of 10, Wonderful, (9)
"We had a great experience. The host was very nice and accommodating. Only thing for people to remember is bring cutlery and plates and cups."
The price is £286
includes taxes & fees
14 May - 15 May
Lakefront Muskoka Beautiful Cottage
Lake
Great Location and Fun For Everyone!
9.6 out of 10, Exceptional, (31)
"Great location and super quiet. Even on a Labour Day weekend. Loved our stay. And our dogs loved the stay too. Would recommend"
Great Location and Fun For Everyone!
Smart TV, fireplace, DVD player, table football
Gorgeous waterfront cottage on beautiful Bear Lake
9.8 out of 10, Exceptional, (55)
"The cottage is bright, fairly clean, and the kitchen has a good amount of dishes, pots and pans. The beds are comfortable as well. It would have been nice to have a working dryer for our mitts and hats. We noticed it had been down since October. Also, an area to hang winter clothes and matts to put winter boots on. We didn't want to put our wet gear directly on the floor. Knowing we were coming and we paid a lot of money to stay plus an additional charge for our fur baby which was more than...
Gorgeous waterfront cottage on beautiful Bear Lake
Smart TV, fireplace, video games, stereo
Muskoka Modern Luxury Lake House Cottage
10.0 out of 10, Exceptional, (1)
"Unfortunately due to a last minute family funeral we were not able to spend the weekend at the cottage but Maryam was very understanding and accommodating. Her place looks amazing and we hope to book her place again this summer."
Muskoka Modern Luxury Lake House Cottage
Property grounds
Cozy Waterfront Cottage on Muskoka River
9.0 out of 10, Wonderful, (4)
"We were very happy with the place. Peaceful, nice, and close to everything. Well supplied kitchen, good barbecue, and way more beds than we needed. Place has a basketball hoop, a volleyball court, and enough green space to place soccer with a small group of people. The river is good for swimming, shallow in the shore but deep as you jump from the dock. Everything was clean and in working order. Thanks to the owners for allowing us to stay at this place."
Cozy Waterfront Cottage on Muskoka River
Exterior
Log Cabin On the Lake B&B
10.0 out of 10, Exceptional, (7)
"Spent my girlfriend’s birthday weekend at the cabin and had the nicest time. Perfect for a quite relaxing weekend with a perfect fire pit area and cozy inside for movie nights"
Log Cabin On the Lake B&B
Fridge, microwave, oven, stovetop
The Serene Acres Cottage Getaway Muskoka
9.6 out of 10, Exceptional, (4)
"My sister and I stayed here for 4 nights while visiting family on Lake Joe. We were pleasantly surprised by the place. We thoroughly enjoyed our stay. The place was exceptionally clean, light-filled with comfortable beds and seating. The kitchen was very well appointed and even had sharp knives. The bathroom had a large tub and shower as well as a stackable w/d in its closet, very useful. The host was pleasant, accommodating and responsive and lives nearby. It was great to rent where the owner...
The Serene Acres Cottage Getaway Muskoka
Property grounds
Muskoka Lakeshore Cottage Bliss, Sleeps 16 in spring, summer, fall, 10 in winter
10.0 out of 10, Exceptional, (4)
"The house on Muskoka Lake was beautiful, 10 min from town, and the rooms were well appointed. The outdoor covered (and screened if desired) deck was perfect for bug free evening hangouts and a place my grandmother could watch the daily shenanigans of her grandkids at the Lake especially when it was raining. We swam, used the 2 adult and 2 kids kayaks and SUP'd every day. The main floor was spacious and kitchen was well stocked with spices and cooking tools. Daphney and her team were very...
Muskoka Lakeshore Cottage Bliss, Sleeps 16 in spring, summer, fall, 10 in winter
Property grounds
Modern Muskoka Retreat
9.8 out of 10, Exceptional, (18)
"This place has EVERYTHING you need in a home away from home, including the best coffee machine I've ever seen. We were only here 2 nights but wish it could have been longer...we had such a great time. You can swim and fish right off the dock and the water was beautiful! Michael was an awesome host and incredibly responsive to any questions we had. And the town is only 7 minutes away, where you can basically get anything you need. I would definitely recommend this place and definitely stay...
Modern Muskoka Retreat
Exterior
Waterfront on Lake Muskoka!
9.6 out of 10, Exceptional, (24)
"Small cottage close to hiking trails. Fair number of other cottages close by but road wasn’t too busy."
Waterfront on Lake Muskoka!
Don't see what you're looking for?
See all available properties in Windermere
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windermere Holiday Rental Travel Info

Number of holiday rentals
10
Popular accommodation
Windermere cottages
Known landmarks
Muskoka Lakes Winery, Aspen Valley Wildlife Sanctuary and Muskoka Lakes Museum
International airport
Toronto, ON (YYZ-Pearson Intl.)

Other types of properties in Windermere you may be interested in

Front of property – evening/night
Windermere House
3.5 star property
8.8 out of 10, Excellent, (360)
"Only reason for "condition" is because not officially open and a lot of construction which did not bother us."
The price is £130
includes taxes & fees
14 May - 15 May
Windermere House
Exterior
JW Marriott The Rosseau Muskoka Resort & Spa
4.5 star property
8.6 out of 10, Excellent, (855)
"Excellent!"
The price is £269
includes taxes & fees
20 May - 21 May
JW Marriott The Rosseau Muskoka Resort & Spa
Lobby
Comfort Inn
2.5 star property
8.6 out of 10, Excellent, (968)
"Great courtesy of personnel. Very quiet place. Clean room."
The price is £70
includes taxes & fees
20 May - 21 May
Comfort Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Windermere holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windermere holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windermere holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windermere. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windermere holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windermere holiday rentals we have selected for you start as low as £108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windermere rentals

At Expedia, we put the best Windermere holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windermere rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windermere holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windermere. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Windermere?

Yes, there are holiday rentals close to the most popular sights in Windermere, or you can select a more secluded option if you're looking for a relaxing stay. Windermere is known for its lake views and golf courses. Make sure you have time to check out the bars and spas during your trip.

What are some of the best holiday rentals that Windermere has to offer?

Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka: This holiday home rental outside of Windermere is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals will I find in Windermere?

Expedia has 5 holiday rentals for your stay in Windermere.

What can I see and do in Windermere?

Explore the area and family-friendly sights such as Santa's Village, or get out into nature at a spot like Lake Rosseau. Other places in town to visit include Windermere Golf & Country Club and Windermere Marina.

What are holiday rentals like in Windermere?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windermere. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.

Recent reviews of Windermere properties
Expedia verified reviews

Sherwood Inn

Sherwood Inn

5/5 Excellent
"My husband and I went there during the Good Friday long weekend just to have a break. It was a 3 days 2 nights get away. Nothing can be seen much in that part of Muskoka since the shops and restaurants there operate on a seasonal basis. But it was nice visiting the place sometimes when it’s quiet. What I like… Located in a beautiful and quiet area in Muskoka Restaurant options Room we stayed 611 Cedarwood is very clean, nice view, good room amenities Staff are friendly and very helpful! Affordable rates Free use of fat bikes Warm atmosphere What needs to be improved… Bed is a bit uncomfortable (spring type). I can feel the springs poking every time I turned and so not much of a comfortable sleep Pillows aren’t comfortable either. Very Lumpy and flat. Not too sure about other rooms, but at Cedarwood, we can hear other guests activity from other rooms. Sound insulation is poor. Our last night in our room was a bit disappointing because the guests from the upper floor kept dragging a chair or something hard on the floor for some reason! Can’t get a good night sleep :( Overall, I will still come back and stay there. Perhaps next time I’ll book a cottage! "
A verified traveller stayed at Sherwood Inn
Posted 23 hours ago
Sherwood Inn