
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

2 min walk to the lake & 20 min drive to Blue Mnt
Lovely, spacious house- 2 min walk to the beautiful & longest freshwater beach in the world. 20 min to Blue Mountain.Lots to do in the area during all seasons: various trails for hiking, biking, 500 Go-Karts & Wasaga Adventure Park, Skydiving & Boat Cruise Wasaga Beach Casino, etc. Adorable 3 Bedroom 2 Bathrooms cottage situated in a beautiful, quiet area perfect for families, friends and couples. This family friendly bungalow is thoughtfully designed for comfort and is packed with amenities

Serenity by Georgian Bay, 4 Season, escape!
This charming, cozy house offers serenity edge of town, by Georgian Bay! Suitable for couples, families and small groups. Across the street from the Bay. Comes with kayak, SUP and lawn games! Close to many Bruce Trails, Scenic Caves trails, or Georgian Trail, and golf. After a busy day exploring or playing, retreat to Meaford and either whip up something delicious in our fully equipped kitchen and dine in with a view of the bay, or walk down Sykes 5 min to one of Meaford's excellent restaurants.

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.

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.

Forest Harbour Hideaway
Situated on beautiful Georgian Bay, this cozy waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock and our brand new custom sauna, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Find a variety of shops, restaurants and local attractions in Midland and Orillia (both a 20 minute drive) like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre!

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

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.

Upscale Spa Getaway w/ Private Sauna
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

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.

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 Collingwood kayak rentals
House rentals with a kayak

The Sixth Great Lake Luxury

Welcoming Waterfront Cottage

The Lake House at Irish

KickBack in Beautiful tranquil central condo

Gorgeous lakeside summer home

The Cedar House

Georgian Bay Vibes, Relax and Reset in Meaford

Ski, Swim, Soak, Boat & Golf
Cottage rentals with a kayak

Lake Eugenia Renovated Waterfront Cottage

Beautiful Lakeside Cottage w/ Sauna

Lake Eugenia all season cottage

Spacious family cottage 45 mins from GTA!

Quiet Waters Getaway

Hot Tub & Sauna Retreat by Georgian Bay Trails

✦9Bedroom✦8400sqft Farm House ✦28Acres ✦1HrToronto

3BR on Lake Simcoe | Gorgeous Views 1hr From City
Cabin rentals with a kayak

The Nest Lakehouse - Hot Tub, Innisfil Beach Park

The Blue Cottage

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Two - YES 2 cozy cabins !

The White Cottage with infinity views

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Cabin 14, A Cozy Muskoka Studio Cabin on the Lake
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$10,460 GYD per night before taxes and fees

Verified guest reviews
Over 490 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
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Cobble Beach Golf Resort Community
- Georgian Bay Islands National Park
- Torrance Barrens Dark Sky Conservation Area
- Burl's Creek Event Grounds
- Scandinave Spa Blue Mountain
- Wasaga Beach Area
- Awenda Provincial Park
- Kee To Bala
- Casino Rama Resort
- Inglis Falls
- Wye Marsh Wildlife Centre
- Forks of the Credit Provincial Park
- Centennial Beach
- Mono Cliffs Provincial Park
- Hockley Valley Resort - Golf, Spa and Ski
- Bass Lake Provincial Park
- Harrison Park
- Sunset Point Park





