
Vacation rentals with a kayak in Collingwood
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Top-rated kayak rentals in Collingwood
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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!

Marina view at Friday Harbour 2bd/2bth Pool option
This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

Valley View Farm Retreat ~ Hiking, Skiing, Pets
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.

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.

"Blue Vue" Georgian Bay Waterfront Cottage
1933 Original cottage on the beautiful clear waters of Georgian Bay just northwest of Meaford, this area offers some of the best swimming, cycling, hiking, fishing and exploring in cottage country. Our private property offers 120 feet of sandy beach with gradual slope into the water and beautiful underwater sandbars right out in front. Situated on a narrow private lane way, this cottage is close enough to town for convenient shopping yet is nestled into a friendly rural cottage community.

The Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Cozy 'Off the Grid" Rustic Cabin
If you enjoy 'roughing it', stay in our beautiful log home from the late 1800's. It has been completely redone, maintaining all of the old character. It is nestled in the edge of the bush, that provides kilometres of hiking trails. The cabin is also situated on a pond so you can spend your days swimming, canoeing, fishing and exploring this nature lover's paradise. Spend your time here unplugging from your everyday life and reconnecting to the healing properties of a natural environment.

Birdsong, the perfect Blue Mountains getaway
Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye to 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.

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons
Well maintained/clean family lake front 4-bedroom cottage with sandy beach entry & 5" off the dock. We offer a large living room with a wood burning fireplace, dining room with full lake views, open kitchen, finished basement rec room with queen pull-out couch and laundry. Access to acres of privately owned forest land great for hiking, mountain biking, ATV’s, snowshoeing, close to the bruce trail, waterfalls and abundant nature. Our ideal guests are families with or without kids.

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

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.
Popular amenities for Collingwood kayak rentals
House rentals with a kayak

Blu Lake House | Waterfront May/June Special

New home|LAKE FRONT|Hot tub|20ft ceilings

Welcoming Waterfront Cottage

New look The Greenview Retreat

The Cedar House

Georgian Bay Vibes, Relax and Reset in Meaford

Ski, Swim, Soak, Boat & Golf

Beaver Valley Farmhouse with Pool & Stunning Views
Cottage rentals with a kayak

Serenity Cottage, Jetski, Hot Tub, Ice rink

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Wasaga on the Water with Loads of Amenities

Lake Eugenia all season cottage

Waterfront Paradise on the Georgian Bay

The Gingerbread House | Near Lake + Wedding Venues

Georgian Bay with Hot Tub & Sauna, on Tay Trail !

Forest Harbour Hideaway
Cabin rentals with a kayak

Hawthorn Cottages - Bunkie #8

The Nest Lakehouse - Hot Tub, Innisfil Beach Park

The Blue Cottage

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Ski, Soak & Warm Up

The MM Hideout
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 G$12,550 GYD per night before taxes and fees

Verified guest reviews
Over 430 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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Caledon Ski Club LTD
- Torrance Barrens Dark Sky Conservation Area
- Kee To Bala
- Inglis Falls
- Harrison Park
- Forks of the Credit Provincial Park
- Burl's Creek Event Grounds
- Bass Lake Provincial Park
- Mono Cliffs Provincial Park
- Casino Rama Resort
- Wye Marsh Wildlife Centre
- Innisfil Beach Park
- Awenda Provincial Park
- Orillia Opera House
- Couchiching Beach Park




