
Vacation rentals with a kayak in Collingwood
Find and book unique kayak rentals on Airbnb
Top-rated accommodations with a kayak in Collingwood
Guests agree: these accommodations with a 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!

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.

Waterfront Sunrise Cottage
Private waterfront cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. With a 150 feet of shoreline shared only with a neighbouring cottage, enjoy the stunning sunrises, relax on a lounger, go for a swim, kayak, paddle board, go fishing or have a camp fire and stargaze. Use our cottage as a jumping off point for many hikes along the Bruce Trail, Sauble Beach (35min), Tobermory (70min) and many more. Or just work from here while enjoying the great view and wifi.

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.

Granny's Cottage
Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

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.

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.

3BR on Lake Simcoe | Gorgeous Views 1hr From City
Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

Orr Lake Oasis
Sit, kick back, laugh & relax in this calm, stress-free, pet-friendly, stylish space with family and friends. Enjoy the great cottage views, games and much more. Drink your favourite drink by the hot tub or by the fire pit overlooking the lake. Take a steam in the barrel sauna just a hop away or take a walk on the local trails. Shop and dine at a tasty local restaurant 10 minutes away or drive out to the city of Midland just under 20 minutes
Popular amenities for Collingwood kayak rentals
House rentals with a kayak

Birdsong, the perfect Blue Mountains getaway

The Cedar House

Sunsets on the beach

Ski, Swim, Soak, Boat & Golf

Lakefront Retreat w/ Hot Tub, Game Room & Beach

Victoria Harbor cottage

Algonquin sunrise on private balcony pond view

Serene Waterfront Escape On Private Lane
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

Charming 3bdrm cottage on Georgian Bay!

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

Waterfront Paradise on the Georgian Bay

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons

The Gingerbread House | Near Lake + Wedding Venues
Cabin rentals with a kayak

Cabin 12, a Cozy 3 Bedroom Muskoka Cabin

Hawthorn Cottages - Bunkie #8

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Cabin 10, Spacious Muskoka 2 Bedroom Cabin

Two - YES 2 cozy cabins !
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 $98 CAD per night before taxes and fees

Verified guest reviews
Over 410 verified reviews to help you choose

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

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Collingwood vacation 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
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Grand River Vacation rentals
- Niagara Falls Vacation rentals
- St. Catharines Vacation rentals
- Northeast Ohio Vacation rentals
- Pittsburgh Vacation rentals
- Erie Canal Vacation rentals
- Laurentides Vacation rentals
- Detroit Vacation rentals
- Mont-Tremblant Vacation rentals
- Rentals with beach access Collingwood
- House rentals Collingwood
- Rentals with breakfast Collingwood
- Townhouse rentals Collingwood
- Chalet rentals Collingwood
- Cottage rentals Collingwood
- Pet-friendly rentals Collingwood
- Fitness-friendly rentals Collingwood
- Rentals with lake access Collingwood
- Beachfront rentals Collingwood
- Rentals with a hot tub Collingwood
- Rentals with a firepit Collingwood
- Apartment rentals Collingwood
- Rentals with outdoor seating Collingwood
- Waterfront rentals Collingwood
- Family-friendly rentals Collingwood
- Condo rentals Collingwood
- Rentals with pools Collingwood
- Cabin rentals Collingwood
- Rentals with a fireplace Collingwood
- Rentals with a patio Collingwood
- Rentals with an EV charger Collingwood
- Rentals with a sauna Collingwood
- Rentals with a washer and dryer Collingwood
- Private suite rentals Collingwood
- Villa rentals Collingwood
- Rentals with a kayak Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Cobble Beach Golf Resort Community
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Bay Resort
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
- Hawk Ridge Golf & Country Club
- Mansfield Ski Club
- King Valley Golf Club
- Legacy Ridge Golf Club
- Inglis Falls
- Heritage Hills Golf Club
- Springwater Golf Course




