Holiday rentals with a kayak in Durham Region

4.92 out of 5 average rating, 167 reviews

Cottage in Brechin

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.

4.89 out of 5 average rating, 117 reviews

Cottage in Ennismore

Luxury Modern Cottage Best Sunrises with Hot Tub

*4 SEASONS COTTAGE*Newly built custom luxury cottage, with brand new beds, mattress, furniture and furnishings. Cottage right on the lake , great fishing right off the dock, amazing boating, east exposure provides the best sunrises right from master bedroom, bon fires lake side, all bedding, linen and towels provided, all life jackets provided, tankless BBQ, ice fishing is available in winter, large hottub, pool table, ping pong, enjoy the canoe, kayaks and SUP. Quarry Golf Club is 5 mins away.

4.98 out of 5 average rating, 101 reviews

Cottage in Trent Lakes

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!

4.82 out of 5 average rating, 173 reviews

Cottage in Bowmanville

Waterfront Beach House Oasis - All Season Hot Tub!

Welcome to our serene waterfront sanctuary! This stunning 4-bed, 3-bath retreat is the perfect escape just outside the city. Enjoy unobstructed lake views, sunsets, kayaks, fire pit, BBQ, and a year-round hot tub. Relax indoors with a movie or on the private pebble beach. Explore nearby Darlington conservation areas for hiking and wildlife. Our home offers everything you need for the ultimate urban getaway. Whether you seek relaxation, adventure, or natural beauty, your perfect retreat awaits!

Guest suite in Port Perry

4.88 out of 5 average rating, 219 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.

4.95 out of 5 average rating, 110 reviews

Cottage in Georgina

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!

Cabin in Nestleton Station

4.92 out of 5 average rating, 147 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.

4.97 out of 5 average rating, 107 reviews

Apartment in Port Perry

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, equip’d kitchen, bath/laundry/EV charger. Pro- designed for peaceful time away. 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! 1 hr from TO, 8 min to Port Perry. We have 2 rms king/queen bedrms.

4.83 out of 5 average rating, 145 reviews

Cottage in Curve Lake

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($).

Home in Nestleton Station

4.99 out of 5 average rating, 130 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.

4.89 out of 5 average rating, 166 reviews

Cottage in Bowmanville

“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!