
Holiday rentals with a kayak in Collingwood
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Top-rated Accommodation with a Kayak in Collingwood
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Relax & enjoy fall- 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

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.

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.

The Avalon - Entire home steps to Meaford Harbour
This newly renovated contemporary 4 season home is the perfect place for couples & families to kick back & relax after a day out exploring. This clean and stylish home is located just steps from the glistening shores of Georgian Bay & in the heart of downtown Meaford. Restaurants, cafes, & boutique shops, are steps away, & a short drive to the hills of Blue Mountain (25min) for a day of skiing makes this the perfect Canadian getaway providing year-round fun. Located just 2 hrs from the GTA.

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.

Forest Harbour Hideaway
Situated on beautiful Georgian Bay, this cozy and quaint waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Both Midland and Orillia are 20 minutes away by car, where you can find a variety of shops, restaurants and local attractions, like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre.

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.

Beach house (with pool open May-Oct)
Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay! Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Modern Country Getaway by the Bay
Enjoy relaxing in our bungalow near Georgian Bay only a 30 min drive to Blue Mountain Village. A perfect base for a family holiday or couples retreat. Beach access is located only 300m from the house. Spend an evening by the fire at our large fire pit. Meaford is nestled in between some of the best fresh water beaches of Sauble and Wasaga.
Popular amenities for Collingwood kayak rentals
Holiday House Rentals with a Kayak

Northwoods Ski Lodge - Georgian Bay Waterfront

The Sixth Great Lake Luxury

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

Luxurious and Beautiful, Barrie

Birdsong, the perfect Blue Mountains getaway

Sunsets on the beach

Victoria Harbour cottage

Serene Waterfront Escape On Private Lane
Cottages with a kayak

Serenity Cottage, Jetski, Hot Tub, Ice rink

Wasaga on the Water with Loads of Amenities

Jewel of Georgian Bay, Luxury Waterfront Cottage

Lake Eugenia Renovated Waterfront Cottage

Charming 3bdrm cottage on Georgian Bay!

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

The Gingerbread House | Near Lake + Wedding Venues

Waterfront Cottage #2
Cabin rentals with a kayak

Hawthorn Cottages - Bunkie #8

The Blue Cottage

Deer Park, Cozy Cabin with Hot Tub, Amazing View

Hawthorn Cottages - Bunkie #1

Two Georgian Bay beach houses

Two - YES 2 cozy cabins !

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

Hawthorn Cottages - Bunkie #2
Quick stats about holiday rentals with a kayak in Collingwood

Total holiday rentals
Explore 10 holiday rentals in Collingwood

Nightly prices starting at
Collingwood holiday rentals start at $122 NZD per night before taxes and fees

Verified guest reviews
Over 410 verified reviews to help you choose

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

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Collingwood holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Cobble Beach Golf Resort Community
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Craigleith Ski Club
- Mount St. Louis Moonstone
- The Georgian Peaks Club
- TPC Toronto at Osprey Valley
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- Toronto Ski Club
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- Alpine Ski Club
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