Holiday rentals with a kayak in Collingwood

4.89 out of 5 average rating, 132 reviews

A cozy living area features warm wooden paneling and a rustic brick wall. A dark purple couch and a wooden coffee table create a welcoming setting. A wood stove is positioned near the entrance, adding a touch of warmth to the space.

Home in Wasaga Beach

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

4.99 out of 5 average rating, 175 reviews

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

Condo in Innisfil

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!

5 out of 5 average rating, 72 reviews

A charming A-frame cabin stands amidst tall grass, with the sun setting in the background. The metal roof glistens softly under the warm light, while large windows reflect the serene surroundings. Wildflowers can be seen in the foreground, adding natural beauty to the scene.

Guesthouse in Meaford

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.

4.85 out of 5 average rating, 188 reviews

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.

Condo in Innisfil

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.

4.84 out of 5 average rating, 167 reviews

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

Cottage in Waubaushene

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.

4.96 out of 5 average rating, 135 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

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.

4.93 out of 5 average rating, 193 reviews

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

Condo in Innisfil

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

4.91 out of 5 average rating, 111 reviews

Red Adirondack chairs are positioned on the dock, overlooking a sandy beach area and a lake. The cottage is visible in the background, surrounded by trees, with colorful kayaks resting on the shoreline. A welcoming atmosphere is created by the spacious outdoor setting.

Cottage in Flesherton

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.

4.99 out of 5 average rating, 135 reviews

A charming wooden cabin stands surrounded by lush green farm fields. Two light-colored chairs are positioned on the porch, providing a welcoming touch. The cabin features large windows and a unique circular entry, complemented by the vibrant greenery of trees and crops nearby.

Tiny home in Kimberley

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

The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.

4.96 out of 5 average rating, 110 reviews

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.

4.84 out of 5 average rating, 243 reviews

Cottage in Innisfil

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

4.84 out of 5 average rating, 267 reviews

A charming cottage exterior is framed by greenery, featuring a balcony with string lights and a Canadian flag. Two pink chairs are positioned on the sandy area in front, and steps lead up to a welcoming entrance with large glass doors.

Cottage in Lafontaine

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.

Popular amenities for Collingwood kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.89 out of 5 average rating, 38 reviews

An aerial view showcases a serene waterfront lined with natural boulders. Lush green trees provide a backdrop, while several homes are visible along the shore, enhancing the peaceful setting. The clear blue water reflects the sky, inviting a sense of tranquility.

Home in Annan

The Sixth Great Lake Luxury

5 out of 5 average rating, 17 reviews

Home in Victoria Harbour

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

5 out of 5 average rating, 11 reviews

A welcoming living area is highlighted by comfortable seating arrangements, including a sofa and two armchairs. A round coffee table sits in the center, surrounded by a soft area rug. A mounted television is above a modern fireplace, with natural light filtering through the windows.

Home in Barrie

Luxurious and Beautiful, Barrie

4.98 out of 5 average rating, 97 reviews

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

Birdsong, the perfect Blue Mountains getaway

5 out of 5 average rating, 19 reviews

A charming cabin exterior is framed by lush greenery, with a welcoming front porch. Five red adirondack chairs are positioned on the manicured lawn, inviting relaxation. The home's distinctive gabled roof and decorative trim add character, complemented by seasonal foliage in the background.

Home in Meaford

The Cedar House

5 out of 5 average rating, 12 reviews

A beachside seating area is positioned on soft sand, featuring a table surrounded by four black metal chairs. The calm sea stretches out in the background, with gentle waves lapping at the shore under a clear blue sky.

Home in Wasaga Beach

Sunsets on the beach

4.87 out of 5 average rating, 90 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

4.63 out of 5 average rating, 8 reviews

An open-concept living area features a stone accent wall and large windows that provide views of Georgian Bay. Comfortable seating arrangements include dark leather sofas and a wooden coffee table. Natural light floods the space, enhancing the warm atmosphere.

Home in Thornbury

Serene Waterfront Escape On Private Lane

Cottages with a kayak

4.98 out of 5 average rating, 54 reviews

A rustic, chalet-style exterior is framed by snow-covered evergreen trees. Warm light spills from the large windows, highlighting the wooden beams and stone accents of the entrance. A pathway lined with snow leads to the front door, flanked by sculptures of animals.

Cottage in Meaford

Serenity Cottage, Jetski, Hot Tub, Ice rink

4.82 out of 5 average rating, 119 reviews

A lakeside cottage is displayed from the dock, featuring a modern design with large windows and a spacious deck. The outdoor area includes a Jacuzzi surrounded by a stone border. Lush greenery frames the scene, enhancing the serene lakeside setting.

Cottage in Gilford

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

4.98 out of 5 average rating, 86 reviews

A serene river reflects the vibrant colors of a sunset sky, with soft pink and orange hues blending with wispy clouds. Lush trees and calm waters create a peaceful ambiance, inviting relaxation and connection with nature.

Cottage in Wasaga Beach

Wasaga on the Water with Loads of Amenities

5 out of 5 average rating, 21 reviews

A comfortable living area features a large sectional sofa alongside a cozy armchair. Sunlight pours through multiple windows that provide views of the lake. A wood-burning stove and a coffee table sit centrally, with wooden walls enhancing the rustic ambiance.

Cottage in Flesherton

Lake Eugenia Renovated Waterfront Cottage

4.95 out of 5 average rating, 59 reviews

A serene view of Georgian Bay is framed by the branches of a tree. A wooden dock extends into the calm water, with a gentle shimmer reflecting sunlight. A grassy area, bordered by a stone wall and a nearby building, complements the tranquil outdoor setting.

Cottage in Meaford

Charming 3bdrm cottage on Georgian Bay!

4.98 out of 5 average rating, 59 reviews

A charming cottage-style home showcases a combination of brick and wood features with a steeply pitched roof. The bright red front door is framed by lush greenery and well-maintained flower beds, enhancing the inviting entryway. A manicured lawn surrounds the home, creating a serene atmosphere.

Cottage in Innisfil

The Gingerbread House | Near Lake + Wedding Venues

4.99 out of 5 average rating, 141 reviews

An aerial view of a cottage located on a waterfront lot is showcased, framed by lush greenery. A large deck and seating areas are visible, along with a hot tub and sauna. Several boats are docked at the waterfront, indicating access to water activities.

Cottage in Alcona

Charming waterfront cottage on Lake Simcoe

4.85 out of 5 average rating, 171 reviews

A welcoming entrance features a wooden gate with the name 'Eagle Point' prominently displayed. A tree-lined gravel driveway leads to a charming cottage with wood siding and a green roof nestled among the trees.

Cottage in Waubaushene

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

Cabin rentals with a kayak

A wooden interior features two single beds in a bunk bed arrangement. Each bed is dressed with a blue and white patterned quilt. A bedside table with a lamp and a small decorative shelf are positioned against the wall, adding functional space.

4.36 out of 5 average rating, 11 reviews

Hawthorn Cottages - Bunkie #8

4.88 out of 5 average rating, 40 reviews

A wooden dock extends into calm waters, featuring two red chairs positioned for relaxation. The surrounding landscape includes lush greenery and several cottages nestled in the background, providing a serene waterfront setting.

Cabin in Elmvale

The Blue Cottage

4.82 out of 5 average rating, 247 reviews

A log cabin exterior is set among lush greenery, featuring a spacious patio area furnished with several chairs and a dining table. Soft natural light illuminates the building, highlighting its natural wood texture and proximity to landscaped flower beds.

Cabin in Kimberley

Deer Park, Cozy Cabin with Hot Tub, Amazing View

A cabin is seen nestled among greenery, featuring a porch with a red roof. A table with benches is positioned nearby on a grassy area. A decorative crane statue stands in front of the cabin, adding character to the outdoor space.

4.93 out of 5 average rating, 14 reviews

Hawthorn Cottages - Bunkie #1

Two cozy cabins are seen at twilight, surrounded by trees. Warm lights illuminate the porches, creating a welcoming atmosphere. A shared outdoor seating area with chairs sits between the cabins, along with a stone ring, suggesting a space for gatherings.

Cabin in Tiny

Two Georgian Bay beach houses

4.97 out of 5 average rating, 37 reviews

A cozy cabin exterior is seen, framed by towering trees and soft earth tones. Two black chairs are positioned in front, and a friendly dog sits contently on the path. Sunlight filters through the trees, creating a serene atmosphere.

Cabin in Southgate

Two - YES 2 cozy cabins !

4.9 out of 5 average rating, 31 reviews

A hot tub is positioned on a deck, surrounded by lush greenery. In the background, a serene view of the water is visible, with a fire pit area furnished with red chairs, enhancing the outdoor experience.

Cabin in Meaford

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

A cabin is set amidst a lush green landscape, featuring a wooden deck with a railing. A picnic table and several lawn chairs are visible in the spacious yard, surrounded by leafy plants and boulders, creating a natural and inviting outdoor environment.