
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

From A to Zen - a refined glamp
A unique and tranquil getaway nestled on the Bruce Trail in the heart of the Niagara Escarpment. A short drive to Georgian Bay, Lake Huron, Blue Mountain, Beaver Valley, Meaford’s harbour and theatre and Owen Sound’s major amenities. Or better yet, just stay put and unwind - paddle the river, bake a gourmet pizza, sunrise coffee on one porch, endless sunsets on another, campfires, kites, disc golf, hike the Bruce, star gaze, and your very own table set for two - straight out of a storybook.

Northwoods Ski Lodge - Georgian Bay Waterfront
Immerse yourself in aqua blue vistas and magnificent sunsets at this family friendly expansive waters edge lodge on Georgian Bay! Take in the breathtaking views from every room with panoramic windows and doors, entertain & dine on the large sun deck, roast marshmallows in the fire pit or explore the bay in your very own kayaks! Shallow cobblestone entry is perfect for little ones! Located minutes from DT Meaford, several beaches, playgrounds & golf course, the perfect home away from home!

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.

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.

Hidden Gem
Welcome to your cozy 1 bedroom basement apartment nestled in a quiet neighbourhood. Enjoy the convenience of being close to amenities, ski hills, bike trails and beautiful Georgian Bay beaches. Step outside to your cozy backyard patio, perfect for morning coffee or evening relaxation. Guests can hit the slopes, partake in local festivals, soak in the beaches or bike to explore the trails, this location caters to your adventurous spirit providing the warmth, comfort relaxation afterwards.

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.

Eugenia Modern Lakehouse
Escape to our newly-built and meticulously cleaned family-friendly cottage nestled right on the shores of beautiful Lake Eugenia. Designed for comfort and relaxation, this bright and modern retreat is perfect for families or small groups looking to unwind in nature — with all the comforts of home. Please note that parties are not permitted at the cottage. Noise travels quickly over the water, and we are committed to maintaining a peaceful and relaxing environment for our neighbours.

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.

New look The Greenview Retreat
Relax with the whole family.2 bedroom/ 2.5 bath with hammock Great place to spend your holiday. Location is 10 minutes from Blue Mountain Skiing. 6 mInutes from Scandinave Spa, 6 minutes from Collingwood’s beautiful downtown shops, restaurants, breweries amd trails. Georgian trail is minutes from the condo. 2 parking spots plus overflow No smoking pets welcome subject to limitations. Kitchen is stocked with utensils
Popular amenities for Collingwood kayak rentals
House rentals with a kayak

Welcoming Waterfront Cottage

Luxurious and Beautiful, Barrie

The Cedar House

Indoor Heated Pool and Sauna Right on the River

Sunsets on the beach

Ski, Swim, Soak, Boat & Golf

Waterfront cottage in Elmvale, Orr Lake

Midland ON - Lakehouse
Cottage rentals with a kayak

Serenity Cottage, Jetski, Hot Tub, Ice rink

Wasaga on the Water with Loads of Amenities

Georgian Bay Getaway - Lakehouse

Charming 3bdrm cottage on Georgian Bay!

Highland Woods Farm | 4BR w/ Private Lake, Sauna +

Waterfront Cottage #2

Forest Oasis in Tay w/Large Jacuzzi Hottub

Georgian Bay with Hot Tub & Sauna, on Tay Trail !
Cabin rentals with a kayak

Hawthorn Cottages - Bunkie #8

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

The Beach Deck Retreat

Hawthorn Cottages - Bunkie #1

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Hawthorn Cottages - Bunkie #2
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.ﺇ257 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 & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

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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