Vacation rentals with a kayak in Durham Region

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Top-rated kayak rentals in Durham Region

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Guest favorite

A wooden deck overlooks tranquil waters, featuring two red Adirondack chairs facing the lake. The beautifully colored sky at sunset casts a serene ambiance, surrounded by lush greenery and trees providing a natural frame.

Cottage in Brechin

4.92 out of 5 average rating, 170 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 favorite

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

4.93 out of 5 average rating, 14 reviews

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

Royal Beach Lakehouse & Spa is your perfect experience of lakeside luxury! Sink your toes into the sand as you relax with your loved ones, our luxury retreat boasts panoramic views of Lake Simcoe! Wake up feeling refreshed after enjoying your private infrared sauna and fun water toys and activities. End your days with a spectacular sunset from your lakeside hot tub & firepit! Our chef's dream kitchen also awaits! This fully equipped lake house is sure to become your next vacation destination!

Top guest favorite

The exterior of the waterfront home is shown, featuring large windows and a spacious upper deck with multiple lounge chairs. A stone pathway leads to the entrance, surrounded by well-maintained green grass and trees, providing a serene backdrop as evening light begins to illuminate the structure.

Cottage in Trent Lakes

4.98 out of 5 average rating, 105 reviews

Lux - 5 Bdrm - Waterfront, Hot Tub, Game Room+Plus

Direct waterfront cottage is perfect for multi family getaway. Situated directly on 160 ft of waterfront on Buckhorn Lake with endless fun. Boasting a hot tub, 30 foot upper deck with glass rail that lights up BLUE at night, beach volleyball, beach area for little ones, master bdrm walkout to deck & breathtaking water views from EVERY bedroom! For the kids and adults alike there is a ping pong table, foosball, pool table, poker table, pac-man arcade, 4 kayaks, 2 SUP, and paddleboat to enjoy!

Guest favorite

A wooden deck features a rectangular glass-top table surrounded by four folding chairs. Lush greenery provides privacy, with a serene lake view and sunset reflected in the water. The space invites relaxation and outdoor enjoyment.

Guest suite in Port Perry

4.88 out of 5 average rating, 231 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 favorite

The image showcases a scenic waterfront view featuring a private dock extending toward a charming cottage. Vibrant red chairs are positioned on the lawn, surrounded by lush greenery. The calm water reflects the blue sky, creating a serene atmosphere for relaxation.

Cottage in Georgina

4.96 out of 5 average rating, 116 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!

Superhost

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

4.91 out of 5 average rating, 157 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 favorite

A modern kitchen is showcased with sleek white cabinetry and contrasting dark hexagonal tiles. A large refrigerator and kitchen counter space are visible, along with a coffee maker and wall clock. Natural light enters through a window, illuminating the contemporary design.

Apartment in Port Perry

4.96 out of 5 average rating, 112 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.

Superhost

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, 147 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 favorite

Home in Nestleton Station

4.99 out of 5 average rating, 136 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

4.9 out of 5 average rating, 172 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!

Guest favorite

A wooden dock extends into a calm lake, reflecting fluffy white clouds and blue skies. Lush greenery is visible along the shoreline, creating a serene natural backdrop.

Cottage in Kawartha Lakes

4.93 out of 5 average rating, 135 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, updated bathroom, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

Top guest favorite

A serene view is presented through large glass windows, showcasing a snowy landscape at dusk. The soft colors of the sunset reflect over the lake, with trees lining the horizon. A cozy chair is positioned on the porch, inviting relaxation amidst the tranquil setting.

Cottage in Brechin

4.92 out of 5 average rating, 108 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.