
Vacation rentals with a kayak in Collingwood
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Quick stats about vacation rentals with a kayak in Collingwood

Total vacation rentals
Explore 10 vacation rentals in Collingwood

Nightly prices starting at
Collingwood vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

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Over 550 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Collingwood vacation rentals include wi-fi 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!
Top-rated kayak rentals in Collingwood
Guests agree: these kayak rentals 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!

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.

Forest Oasis in Tay w/Large Jacuzzi Hottub
Beautiful cottage situated on the most southern point of Georgian Bay in Victoria Harbour. Less then 2 hours from the GTA with full amenities including an LCBO and Foodland 5 minutes away. Take advantage of plenty outdoor activities. Enjoy a bike ride on the stunning Tay Shore Trail, swimming in the lake on a hot summer day or hit the local slopes at Mt St Louie during the winter. Regardless of your choice in activities, end the evening with a soak in the hottub. Don't forget to look for stars!

Lakefront | Hot Tub, Private Dock & Sandy Bottom
Luxury lakefront cottage on beautiful Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub, perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQ, and a fire pit. Ideal for family vacations and group getaways near Toronto, minutes from Hwy 404. Features 6 spacious bedrooms, 4 bathrooms, a fully equipped chef's kitchen, and a bright open-concept living area. Private, peaceful, and perfect for unforgettable memories.

Ultimate Georgian Bay Vacation Getaway
Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

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.

Boho Beaver Cabin 1 with saltwater hot tub & sauna
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 and sauna. 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

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.

MapleHaven Cabin @ Lake Eugenia
A rustically elegant log cabin sitting on an acre of beautiful mature maple trees on a quiet dead-end street. Find peace and tranquility in the rustic atmosphere the log cabin setting provides, but enjoy all of the comforts of home. Enjoy 3 bedrooms ,2 baths with a master bedroom that features a coffee bar and covered balcony . Located at Lake Eugenia, in the heart of the scenic Beaver Valley, a 4 seasons playground. Walking distance to public beach/boat launch.

Modern Country Getaway by the Bay
Enjoy relaxing in our bungalow just a two minute walk to Georgian Bay and only a 30 min drive to Blue Mountain Village. Surrounded by mature trees and fresh lake air, the property offers stillness of the countryside. A great home base for a family holiday or couples retreat. Perfect for unwinding after a day outdoors. As evening falls, gather around our large outdoor fire pit, slow down, recharge, and reconnect with nature.
Popular amenities for Collingwood kayak rentals
House rentals with a kayak

Algonquin sunrise on private balcony pond view

The Lake House at Irish

The Cedar House

Waterfront cottage in Elmvale, Orr Lake

Welcoming Waterfront Cottage

Sweeping Views - Beaver Valley Farmhouse & Pool

The Hidden Haven Cottage

Private river access with pool, canoes, kayak
Cottage rentals with a kayak

Waterfront Paradise on the Georgian Bay

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Spacious family cottage 45 mins from GTA!

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Forest Harbour Hideaway

Georgian Bay Waterfront Cottage HotTub King Bed

Cottage on the lake
Cabin rentals with a kayak

Deer Park, Cozy Cabin with Hot Tub, Amazing View

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Hawthorn Cottages - Bunkie #1

The White Cottage with infinity views

The MM Hideout

Two - YES 2 cozy cabins !

Cozy 'Off the Grid" Rustic Cabin

Lake view Blue cabin by the bay
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