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Holiday rentals with a kayak in Durham Region

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Top-rated rentals with kayak in Durham Region

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite
Cottage in Brechin
4.92 out of 5 average rating, 174 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect spot for bringing together family and friends. Here, laughter fills the home, and nature's beauty is right outside your door. Dive into clear waters for some fun kayaking and boating, and wake up to beautiful sunrises from our private dock. Take a walk on scenic paths, enjoy outdoor BBQs, and paddle around in our kayaks. Book your special getaway today and start making heartwarming memories that last.

Guest favourite
A spacious backyard features a fire pit surrounded by four adirondack chairs. The cottage showcases large windows and a deck with outdoor dining furniture and an umbrella. Two kayaks are stored nearby, adding to the lakefront atmosphere.
Home in Little Britain
4.96 out of 5 average rating, 105 reviews

Cozy Lakeside Cottage on Lake Scugog

WELCOME TO OUR COZY COTTAGE! This rustic, private, lakefront cottage (north shore of Lake Scugog) 2 bedrooms (1 queen, 1 full/double sized bed), large bright sunroom with sleeper sectional. Large newly renovated deck. You are sure to enjoy the lake view, large private dock, water facing deck with bbq, huge yard for games, bon fires and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for couples or friends to escape the hustle and bustle, relax and unwind.

Guest favourite
A fire pit with flames is situated near the water's edge, surrounded by smooth stones. An Adirondack chair is positioned to face the lake, offering a view of the serene water and a colorful sunset in the background.
Guest suite in Port Perry
4.88 out of 5 average rating, 240 reviews

Sunset Haven

Cozy suite, this location provides the very best of the outdoors for cottaging enthusiasts 45 minutes from the GTA. Found on the outskirts of Port Perry near the Blue Heron Casino and on the shores of Lake Scugog, you will find great fishing, swimming, and boating at your doorstep. Also great lounging on the deck/dock! The casino is 5 min drive and the town of Port Perry with its good restaurants and shopping is 10 min car ride or take your boat! Unfortunately, no pets are allowed by guests.

Guest favourite
A spacious living area features a high vaulted ceiling and large windows that provide sweeping views of the lake. A stone fireplace and a modern TV complement the cozy seating arrangement, which is paired with a stylish dining area, ensuring a comfortable gathering space.
Cottage in Georgina
4.95 out of 5 average rating, 121 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Guest favourite
A backyard view features a grassy area with stone pathway leading to a dark exterior cottage. Outdoor furniture, including a dining table and chairs, is situated nearby. Large windows offer glimpses of the serene environment, with a barbecue grill positioned to the side.
Bungalow in Georgina
4.82 out of 5 average rating, 103 reviews

Lake Simcoe Retreat

Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

Guest favourite
A lakefront cottage is set on a grassy area beside the water, featuring a wooden dock extending toward the lake. The exterior shows a welcoming porch and surrounding trees provide shade. Stone borders accentuate the shoreline, creating a natural beach-like atmosphere.
Cabin in Nestleton Station
4.92 out of 5 average rating, 167 reviews

Cozy, Quirky and Modern Lakefront Cottage

Welcome to the Scugog Sugar Shack! Just 70 mins away from Toronto, escape to enjoy picturesque sunsets at this cozy lakefront cottage nestled under the largest collection of mature sugar maples on Scugog Point. This 2 bedroom open concept 1940s cottage has been updated with all the creature comforts while staying true to its quirky roots. With private access to Lake Scugog, known for fishing, kayaking, paddle boarding and swimming, bask in the sun all day & sit by a fire under the stars.

Top guest favourite
Flat in Port Perry
4.97 out of 5 average rating, 122 reviews

Romantic & Cozy Countryside luxury loft with views

Romance in the Country. Getaway from the hustle with your sweetheart, to play, rest/work stay-cation. Newly built, full kitchen, bath/laundry/EV charger. Great trails, theatre, shopping in quaint downtown Port Perry, boating, golfing, equestrian farm, museums, & amazing 5 star restaurnts in Port Perry. Enjoy the pond on the property & lots of places to enjoy peace & quiet together! Ask about our Chef and Pontoon experiences. 1 hr from TO, 8 min to Port Perry. We have 2 rms queen loft/king.

Guest favourite
An aerial view of the cottage situated near the Upper Buckhorn Lake is presented. The property is surrounded by lush trees, with a private dock extending into the water. Nearby, a well-maintained lawn features a circular firepit area and neatly arranged trees.
Cottage in Curve Lake
4.84 out of 5 average rating, 149 reviews

Luxury Log Cottage With Hot Tub And Sauna($)

Luxury Year around log Cottage, located up on the beautiful Upper Buckhorn Lake. This one of a kind property is only 1.5 hrs. from GTA. Enjoy paddle board, canoeing, waterfront, hot tub, firepit, BBQ, fishing, cozy fire place, free WIFI, AC, Fully equipped high end kitchen, private dock, quiet treed neighborhood, all the amenities for an outstanding getaway! 10 minutes drive to Buckhorn Centre. Near to Golf Courses, shopping and dining and hiking. Wood stove Sauna available upon request($).

Top guest favourite
Home in Nestleton Station
4.99 out of 5 average rating, 147 reviews

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

Superhost
A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.
Cottage in Bowmanville
4.89 out of 5 average rating, 177 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

Top guest favourite
The living room features wooden walls and beams with ample natural light from a large window. A grand piano is positioned next to a cozy armchair, complemented by a clock above a stone fireplace. A colorful rug adds a touch of warmth to the space.
Cottage in Brechin
4.92 out of 5 average rating, 117 reviews

Cottage on Lake Simcoe Amazing lake Views

Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

Top guest favourite
The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.
Guest house in Port Perry
5 out of 5 average rating, 136 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

Popular amenities for kayak rentals in Durham Region

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favourite
The exterior of a lakeside cottage is shown, featuring a large wooden deck and a covered seating area. Surrounding foliage includes tall trees reflected in the water, which mirrors the clear blue sky. Direct access to the shoreline enhances its tranquil setting.
Home in Peterborough
4.93 out of 5 average rating, 46 reviews

Kawartha Lakes , Chemong lake front property

Guest favourite
A fire pit area is surrounded by multiple Muskoka chairs, with a vibrant fire burning in the center. The expansive lawn is meticulously landscaped, framed by lush greenery and a view of the lake house's covered porch, illuminated by soft evening light.
Home in Georgina
4.95 out of 5 average rating, 20 reviews

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

Guest favourite
A tranquil lake view is presented, featuring a boat docked beside a spacious wooden dock. The water reflects the clouds and sunset hues, creating a serene atmosphere. Two kayaks rest on the side, awaiting adventure, while the gentle ripples hint at the lake’s calmness.
Home in Little Britain
4.92 out of 5 average rating, 26 reviews

Luxurious waterfront paradise on lake Scugog

Top guest favourite
A serene exterior view of a modern home features a spacious deck with red umbrellas, inviting outdoor seating. Lush green grass surrounds the property, while trees provide a natural backdrop. The architecture showcases angular roofs and multiple windows, creating a welcoming atmosphere.
Home in Uxbridge
5 out of 5 average rating, 37 reviews

Udora house on the river!

Superhost
A modern two-story cottage is showcased with a combination of stone and wood siding. Large windows allow natural light to fill the space. A clean, paved walkway leads to the entrance, surrounded by newly landscaped greenery, including shrubs and small trees.
Home in Kawartha Lakes
4.75 out of 5 average rating, 8 reviews

Cottage #5 on Sturgeon Lake, Hot Tub, Water Toys

Guest favourite
A spacious living area features a large dining table surrounded by wooden chairs. A cozy sectional sofa is positioned in front of a 120-inch 4K projector, displaying a streaming service menu. Natural light pours in through multiple large windows, creating a bright atmosphere.
Home in Bowmanville
4.89 out of 5 average rating, 87 reviews

Axe-Throwing, Private Beach, Hot Tub & Home Cinema

Superhost
An outdoor seating area features five wooden Adirondack chairs arranged around a stone firepit. A stone patio extends out to a grassy area, with a lake view in the background and a dock visible on the right, along with two kayaks.
Home in Buckhorn Lake
4.73 out of 5 average rating, 63 reviews

Kawartha Waterfront Cottage - Low Pricing

Guest favourite
Home in Ennismore
4.9 out of 5 average rating, 10 reviews

Waterfront Escape | Hot Tub, Sauna, Pet Friendly

Cottage rentals with a kayak

Top guest favourite
A serene outdoor space is featured, illuminated by soft lights under a night sky. A patio area hosts a seating arrangement, surrounded by lush greenery and a fire pit. The water is visible in the background, enhancing the tranquil setting.
Cottage in Beaverton
5 out of 5 average rating, 41 reviews

Private Waterfront Cottage at Lake Simcoe

Guest favourite
Cottage in Caesarea
5 out of 5 average rating, 27 reviews

Entire Lakefront Cottage Over Xmas or NYE

Top guest favourite
The spacious kitchen features modern cabinetry and a large island with seating for four. Stainless steel appliances are neatly integrated, with soft under-cabinet lighting illuminating the countertops. A subtle color palette enhances the clean and open design, making the area inviting for meal preparation.
Cottage in Lakefield
4.99 out of 5 average rating, 76 reviews

Luxury Waterfront Cottage (5,000 sqft w/ Hot Tub)

Superhost
An outdoor dining area is set on a wooden deck overlooking the lake. A rectangular table is surrounded by four chairs, with an umbrella providing shade. A gas BBQ is positioned under a pergola, offering convenience for outdoor meals. The calm water reflects the clear blue sky.
Cottage in Scugog
4.71 out of 5 average rating, 7 reviews

Waterfront Cottage - Fire Pit, Dock, 1Hr Toronto

Guest favourite
Cottage in Little Britain
4.9 out of 5 average rating, 40 reviews

Cozy All-Season Lakeside Cottage with Sauna

Superhost
The cottage features a rustic exterior with a stone chimney and large windows, inviting natural light. Below, red Adirondack chairs are arranged around a fire pit, creating a cozy outdoor gathering space. Lush greenery surrounds the seating area, enhancing the lakeside setting.
Cottage in Kawartha Lakes
5 out of 5 average rating, 4 reviews

*The Loon Street Lodge ! * A Lakefront Cottage !

Guest favourite
Two wooden Adirondack chairs are positioned on a sandy area facing a tranquil lake. A fire pit surrounded by smooth stones is nearby, creating a peaceful setting. The calm water reflects the surrounding trees and distant cottages, contributing to a serene outdoor atmosphere.
Cottage in Kawartha Lakes
4.94 out of 5 average rating, 32 reviews

Dreamy 2BR Cottage on point, surrounded by water

Guest favourite
A spacious outdoor area features multiple seating arrangements illuminated by soft lighting. A cozy firepit is surrounded by inviting seating, creating a perfect space for gatherings. The multi-tiered deck opens up to the cottage, with a clear view of the landscaped surroundings.
Cottage in Kawartha Lakes
4.85 out of 5 average rating, 48 reviews

4BR Waterfront Retreat w/Barrel Sauna & Firepit

Cabin rentals with a kayak

The exterior of a cottage is visible, featuring a wooden deck with stairs leading to the entrance. Lush greenery lines the walkway and yard, while telephone poles and wires extend across the background. The road alongside the property is partially observed.
Cabin in Beaverton
4.88 out of 5 average rating, 57 reviews

Thorah Centennial park Lake Simcoe Beaverton Ont

A green bicycle sculpture with colorful flower spokes and a 'welcome' sign is positioned in the foreground. In the background, a two-story cottage with cream-colored siding and red roof accents is visible. The surrounding area includes landscaped grass and a paved driveway.
Cabin in Kawartha Lakes
4.5 out of 5 average rating, 12 reviews

R & R Hideaway

A wooden dock adorned with red Adirondack chairs and a parasol offers a tranquil outdoor space overlooking still water, reflecting lush greenery and the cottage in the background. Tall grasses frame the area, providing a natural border along the peaceful lakeside.
Cabin in Uxbridge

Margaret's Luxury Lake Cottage

Superhost
A rustic cottage features a large screened-in porch, providing a comfortable space to enjoy the outdoors. The exterior showcases a sloped roof, wood paneling, and a grassy area with several Adirondack chairs arranged around a picnic table, perfect for relaxation.
Cabin in Kawartha Lakes
4.71 out of 5 average rating, 181 reviews

Cute Rustic Balsam Lakefront Cottage 4 Season

A charming cottage is nestled among trees, featuring a spacious deck with outdoor seating and shaded areas. Two paddle boards are secured against the cottage, highlighting easy access to water activities. Lush green grass surrounds the structure, adding to the inviting outdoor space.
Cabin in Kawartha Lakes
4.67 out of 5 average rating, 6 reviews

The Cedar Cottage

Guest favourite
A warm wooden cabin is illuminated by soft outdoor lighting, surrounded by tall trees. A small porch with steps leads to the entrance, while a gravel area in front adds to the rustic charm. The setting evokes a serene atmosphere in a natural landscape.
Cabin in Beaverton
4.95 out of 5 average rating, 40 reviews

Riverside Cabin Getaway

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