
Vacation rentals near Waterview Trail Trailhead
We found 599 vacation rentals — enter your dates for availability
Choose the perfect vacation rental within close proximity to Waterview Trail Trailhead. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, like WiFi and a washer and dryer. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Waterview Trail Trailhead
Showing deals for:Nov 14 - Nov 21
Image gallery for Luxurious Lake front Island Twnhome Friday Harbour

8.88.8 out of 10 rating
Excellent
(9 reviews)
Luxurious Lake front Island Twnhome Friday Harbour
Innisfil, ON
10% off
Price is CA $294
CA $294
CA $2,803 total
CA $2,803 total
includes taxes & fees
Image gallery for Friday Harbour Prime Location - Luxurious Lakeside Escape

1010 out of 10 rating
Exceptional
(5 reviews)
Friday Harbour Prime Location - Luxurious Lakeside Escape
Innisfil, ON
25% off
Price is CA $225
CA $225
CA $2,259 total
CA $2,259 total
includes taxes & fees
Image gallery for Luxury Lake Simcoe Waterfront Cottage

1010 out of 10 rating
Exceptional
(5 reviews)
Luxury Lake Simcoe Waterfront Cottage
Innisfil, ON
15% off
Price is CA $1,639
CA $1,639
CA $14,754 total
CA $14,754 total
includes taxes & fees
Image gallery for Amazing Waterfront, Cottage at Big Bay Point

9.69.6 out of 10 rating
Exceptional
(33 reviews)
Amazing Waterfront, Cottage at Big Bay Point
Innisfil, ON
10% off
Price is CA $585
CA $585
CA $5,552 total
CA $5,552 total
includes taxes & fees
Image gallery for Gorgeous and spacious Winfield Chalet just steps away from Georgian Bay!

1010 out of 10 rating
Exceptional
(10 reviews)
Gorgeous and spacious Winfield Chalet just steps away from Georgian Bay!
Victoria Harbour, ON
5% off
Price is CA $380
CA $380
CA $3,498 total
CA $3,498 total
includes taxes & fees
Image gallery for 4 Bedroom Cottage on beautiful stretch of the Severn River west of sparrow lake.

9.29.2 out of 10 rating
Wonderful
(5 reviews)
4 Bedroom Cottage on beautiful stretch of the Severn River west of sparrow lake.
Severn, ON
10% off
Price is CA $450
CA $450
CA $4,179 total
CA $4,179 total
includes taxes & fees
Image gallery for Secluded family cottage on Sparrow Lake, Muskoka

9.29.2 out of 10 rating
Wonderful
(15 reviews)
Secluded family cottage on Sparrow Lake, Muskoka
Severn, ON
19% off
Price is CA $395
CA $395
CA $3,632 total
CA $3,632 total
includes taxes & fees
Image gallery for Need a summer getaway? Book NorthFork Lakehouse-the ultimate cottage destination

1010 out of 10 rating
Exceptional
(23 reviews)
Need a summer getaway? Book NorthFork Lakehouse-the ultimate cottage destination
Carden, ON
5% off
Price is CA $753
CA $753
CA $6,852 total
CA $6,852 total
includes taxes & fees
Image gallery for Waterfront Luxury with Pool

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Waterfront Luxury with Pool
Innisfil, ON
15% off
Price is CA $1,821
CA $1,821
CA $15,902 total
CA $15,902 total
includes taxes & fees
Image gallery for Cozy 4 Season Cottage stunning sunsets on Sparrow Lake!(Pet friendly)New Hot Tub

1010 out of 10 rating
Exceptional
(7 reviews)
Cozy 4 Season Cottage stunning sunsets on Sparrow Lake!(Pet friendly)New Hot Tub
Severn Bridge, ON
19% off
Price is CA $385
CA $385
CA $3,547 total
CA $3,547 total
includes taxes & fees
Image gallery for Comfy Waterfront Cottage - 10 min from Casino Rama

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Comfy Waterfront Cottage - 10 min from Casino Rama
Ramara, ON
10% off
Price is CA $351
CA $351
CA $3,426 total
CA $3,426 total
includes taxes & fees
Image gallery for Luxury Lake Home with Hot Tub and Pool

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury Lake Home with Hot Tub and Pool
Carden, ON
10% off
Price is CA $1,395
CA $1,395
CA $12,213 total
CA $12,213 total
includes taxes & fees
Image gallery for Barrie Kempenfelt Bay Waterfront Cottage(Muskoka by the City)

9.09.0 out of 10 rating
Wonderful
(16 reviews)
Barrie Kempenfelt Bay Waterfront Cottage(Muskoka by the City)
Shanty Bay, ON
15% off
Price is CA $438
CA $438
CA $4,013 total
CA $4,013 total
includes taxes & fees
Image gallery for CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH

9.89.8 out of 10 rating
Exceptional
(23 reviews)
CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH
Barrie, ON
5% off
Price is CA $166
CA $166
CA $1,599 total
CA $1,599 total
includes taxes & fees
Image gallery for Entire lakeside cottage with 6 person hot tub

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Entire lakeside cottage with 6 person hot tub
Carden, ON
10% off
Price is CA $537
CA $537
CA $5,142 total
CA $5,142 total
includes taxes & fees
Image gallery for Georgian Bay waterfront cottage in a quiet cove w/HOT TUB

1010 out of 10 rating
Exceptional
(10 reviews)
Georgian Bay waterfront cottage in a quiet cove w/HOT TUB
Victoria Harbour, ON
10% off
Price is CA $630
CA $630
CA $5,850 total
CA $5,850 total
includes taxes & fees
Image gallery for Luxury Guest House With Private Hot Tub and Trails

1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Guest House With Private Hot Tub and Trails
Oro-Medonte, ON
10% off
Price is CA $190
CA $190
CA $1,950 total
CA $1,950 total
includes taxes & fees
Image gallery for Log Cabin On the Lake B&B

9.69.6 out of 10 rating
Exceptional
(33 reviews)
Log Cabin On the Lake B&B
Gravenhurst, ON
10% off
Price is CA $224
CA $224
CA $2,037 total
CA $2,037 total
includes taxes & fees
Image gallery for Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour, ON
19% off
Price is CA $117
CA $117
CA $1,266 total
CA $1,266 total
includes taxes & fees
Image gallery for Pet Friendly Beach House with Bunkie Bar & Hot Tub

9.29.2 out of 10 rating
Wonderful
(5 reviews)
Pet Friendly Beach House with Bunkie Bar & Hot Tub
Chippewas of Rama First Nation, ON
8% off
Price is CA $683
CA $683
CA $6,186 total
CA $6,186 total
includes taxes & fees
Image gallery for Shallow Beach Lakefront Cottage perfect with Kayak, Firepit, BBQ + Playground

9.49.4 out of 10 rating
Exceptional
(8 reviews)
Shallow Beach Lakefront Cottage perfect with Kayak, Firepit, BBQ + Playground
Innisfil, ON
10% off
Price is CA $759
CA $759
CA $7,069 total
CA $7,069 total
includes taxes & fees
Image gallery for Family Getaway On Lake Couchiching - Cumberland Beach

1010 out of 10 rating
Exceptional
(6 reviews)
Family Getaway On Lake Couchiching - Cumberland Beach
Severn, ON
10% off
Price is CA $878
CA $878
CA $8,224 total
CA $8,224 total
includes taxes & fees
Image gallery for "Take It Easy" cottage w/ Hot Tub & Finnish Sauna

9.49.4 out of 10 rating
Exceptional
(28 reviews)
"Take It Easy" cottage w/ Hot Tub & Finnish Sauna
Severn, ON
20% off
Price is CA $400
CA $400
CA $3,863 total
CA $3,863 total
includes taxes & fees
Image gallery for Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario

1010 out of 10 rating
Exceptional
(6 reviews)
Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario
Severn, ON
10% off
Price is CA $456
CA $456
CA $4,297 total
CA $4,297 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waterview Trail Trailhead
Lakefront Cottage w/Hot Tub, BBQ Grill, Patio, Fire Pit, Dock, Sauna, Fire Place
Sleeps 13 · 5 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property
Sleeps 8 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
Two Story Boathouse Located On East Side of Lake Simcoe
Sleeps 4 · 2 bedrooms · 0+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Sandy Beach Cottage steps to Lake Simcoe - 1 hr 20 mins from Toronto
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Swing Bridge Cottage on Lake Simcoe - Waterfront
Sleeps 8 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated rentals - Waterview Trail Trailhead
Great getaway spot
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Very clean, super friendly. A great spot to simply sit back and relax.
Glen B.
Stayed Jul 2025
Great getaway
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
I stayed here with my husband and in-laws - what a fantastic place. Enough space for everyone to either hang out together or have their own space. The barn was such a great place to hang out too. All in all, a great time. Would stay again!
Justine K.
Stayed Jul 2025
Summer weekend
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Great time at the cottage! Everything was as advertised and described.
Julianna G.
Stayed Jul 2025
Great stay, great host!
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
We had a fantastic stay at this lakehouse! The host was incredibly welcoming and responsive. The lake itself was crystal clear and perfect for swimming and relaxing—especially with all the floaters provided. The property was packed with great activities: a cozy fire pit, a peaceful hammock, and even a white sand beach that made it feel like a private getaway. The location was ideal—close to charming local spots, yet still felt like a retreat. The house was clean, comfortable, and had everything we needed—including amazing Wi-Fi, which was a pleasant surprise for a lakeside property. Highly recommend for anyone looking for a relaxing and well-connected escape!
Sandy G.
Stayed Jul 2025
Cleaning and well-equipped property!
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
We had a very pleasant stay at this condo in Friday Harbour.Check-in was seamless, and the host, Kin, provided clear and detailed instructions.This condo is one of the cleanest and most well-equipped places we’ve ever stayed in. We usually sanitize the space ourselves upon arrival, but this unit was spotless and left us with very little to do. Everything was in excellent working condition and thoughtfully stocked—even a full set of seasonings was provided.The location is great for our liking - close to both the harbour front and the nature reserve trails. We especially appreciated being on the ground floor, which made coming and going easy through the patio. Despite being at ground level, the unit felt private and quiet.We would definitely recommend this condo to friends and family, and would love to stay here again in the future.
Lindsay L.
Stayed Jul 2025
Lovely comfortable cottage
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The owner was very quick to rely to questions I had Very nice cottage washroom and grounds. We had a very good stay
Barbara M.
Stayed Jun 2025
Excellent Stay
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
We enjoyed our stay and recommend this cottage to anyone who is looking for a place to relax, and doesn't mind the absence of a lake on the property.For us it was the perfect weekend getaway.
Steven S.
Stayed Jun 2025
Perfect
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Very nice
Neha C.
Stayed May 2025
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value