
Holiday rentals with a kayak in Collingwood
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Top-rated rentals with kayak in Collingwood
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Sunrise and Bayview with Kayaks & Bikes
🌊 Bright and inviting waterfront/view ground level apartment in the heart of Meaford. 👋Entire apartment to yourself 👥Ideal for a romantic getaway 🏔20 minute drive to Blue Mountain attractions. 2 hours from Bruce Peninsula National Park 🏖 5 minute stroll to the Harbour and Sandy Beach or a pebble beach right across the road ! 🚶‍♂️Walking distance to Meaford Hall 🍽Dining options a block away:) Kayaks, Bikes, Floaties, snowshoes and snorkels are complimentary. Come and discover our gem of a town

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Luxury Waterfront Cottage Hot Tub & Amazing Sunset
Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

Valley View Farm Retreat ~ Family, Pets, Hiking
Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

2 minute walk to the beach / games room
Beautiful and charming home, 2 min walk to the beach, 20 min drive to Blue Mountain and Scandinave Spa. High speed WiFi, 3 TVs, spacious and elegantly decorated rooms perfect for families to connect. Central AC, 2 gas fireplaces. Fully equipped kitchen, fire pit, and gas BBQ. Games room with arcade games, pool table, basketball game, foosball table. Minutes to Canadian Tire, Walmart, LCBO, Tim Hortons, Starbucks and brand new Wasaga Beach casino, come relax and enjoy this amazing get away.

Waterfront Paradise on the Georgian Bay
This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle boat for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

Muskoka Stunning Cottage On Little Lake
Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Birdsong, the perfect Blue Mountains getaway
Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye for the eclectic and enjoyable. This enchanting vacation property boasts an enormous hot tub that doubles as a heated indoor pool; as well as a sauna, well-equipped boutique gym, pool table, dedicated conference room/business center, outdoor fire pit and treehouse for kids. Surrounded by the gorgeous Blue Mountains, Birdsong is the perfect ski season rental; as well as summer family getaway.

Ski, Swim, Soak, Boat & Golf
Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

Boho Vintage Box Car Utopia
Escape to a one-of-a-kind retreat in a beautifully renovated 2-bedroom vintage boxcar with a private hot tub. High speed internet available for entertainment or a work vacation. Located on Rustic Roots Farm & Eco-Retreat just 1 hr north of Toronto. Explore 64 acres of trails, relax by the spring-fed pond, enjoy bonfires, or fish along the winding Nottawasaga River. With organic gardens, wildlife, and birdwatching all around, it’s the perfect place to slow down and reconnect.

Boho Beaver Cabin 1 with saltwater hot tub
So close, yet so far. Only 2 hours north of Toronto, 15 minutes to the base of Blue Mountain. This 108 square foot of "adorable" offers a four-season experience with a communal salt water hot tub. A river runs through it, the majestic Beaver River! This charming, boho inspired tiny cabin for two is nestled on an 80 acre property surrounded by farm fields, wildflowers, and ancient woodlands Check out our social media for more information and photos at: @BohoBeaver

Modern Waterfront Home on Georgian Bay w/ Hot Tub!
Escape to a peaceful haven with this new and breathtaking modern waterfront cottage. Immerse yourself in the stunning views from the walkout deck with outdoor seating, a hot tub and a BBQ area. Quiet neighbourhood in Victoria Harbour on Georgian Bay. Short drive to charming town of Midland and nearby attractions such as the Tay Shore Trail and the Wye Marsh Wildlife Centre. This bright and beautifully finished home is less than a 2-hour drive from the GTA.
Popular amenities for kayak rentals in Collingwood
House rentals with a kayak

Blu Lake House | Waterfront May/June Special

Private river access with pool, canoes, kayak

River's End: Explore the river by kayak or canoe!

The Lake House at Irish

Modern Country Getaway by the Bay

KickBack in Beautiful tranquil central condo

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

The Cedar House
Cottage rentals with a kayak

CozyPeaceful LakeCottage HotTub Canada

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

The Bay View Cottage w/hot tub

Granny's Cottage

Waterfront Muskoka Cottage on Trent-Severn River

Balmy Breezes - Waterfront Cottage with Hot Tub

AMIGO LAKE HOUSE

Hot Tub & Sauna Retreat by Georgian Bay Trails
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

Hawthorn Cottages - Bunkie #1

Lake view Blue cabin by the bay

Two - YES 2 cozy cabins !

The White Cottage with infinity views

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Beautiful Vacation Home with a Large Backyard.

MapleHaven Cabin @ Lake Eugenia
Quick stats about holiday rentals with a kayak in Collingwood

Total holiday rentals
Explore 10 holiday rentals in Collingwood

Nightly prices starting at
Collingwood holiday rentals start at ÂŁ37 per night before taxes and fees

Verified guest reviews
Over 490 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Collingwood holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Collingwood rentals

4.9 Average rating
Collingwood stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a kayak Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Torrance Barrens Dark Sky Conservation Area
- Scandinave Spa Blue Mountain
- Cobble Beach Golf Resort Community
- Burl's Creek Event Grounds
- Wye Marsh Wildlife Centre
- Centennial Beach
- Awenda Provincial Park
- Kee To Bala
- Wasaga Beach Area
- Inglis Falls
- Casino Rama Resort
- Forks of the Credit Provincial Park
- Caledon Ski Club LTD
- Bass Lake Provincial Park
- Mono Cliffs Provincial Park
- Harrison Park
- Sunset Point Park





