Vacation rentals with a kayak in Greater Toronto and Hamilton Area

Rustic Ridge

Rustic Ridge Tiny Cabin - Cozy Escape on Private Pond **Cabin will have to be winterized when temperature drops meaning no running water and outdoor shower, jugs of water will be supplied to rinse after sauna, bottled water in dispenser also provided.*** Welcome to Rustic Ridge Tiny Cabin, a unique shipping container retreat on the back of our property. Nestled by a private pond with a fountain, this serene cabin is the perfect escape for nature lovers and those looking to unwind in comfort.

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!

Lake Ontario Home+Hot Tub, sleeps 10 | Tucked Away

Retreat to a secluded corner of Lake Ontario at this family-sized lakefront home! Nestled between the lake and a state park Tucked Away is just that - a cozy, peaceful, lakeside hideaway. Here you can enjoy waking up to the crashing waves, the stunning sunsets behind the Toronto skyline from the hot tub and bringing your dogs down to the beach for a swim. From families to couples, this house caters to everyone with its close proximity to hiking trails, wineries, family excursions, and more!

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

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.

Lakefront Home for 4 | 2 BR, Hot Tub, Fire Pit

Welcome to your private Kawartha Lakehouse retreat! This spacious home is the perfect luxury escape for couples, small families, or friends who want extra room to spread out and relax. Enjoy the comfort of a full-size lakehouse with only 2 bedrooms, giving you both privacy and space in a tranquil lakeside setting. Whether you’re planning a romantic getaway, a family trip with kids, or a work-from-the-lake escape, our home offers a cozy setup with the space and privacy of a full lakehouse.

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JUNE 30 (today) JULY 8-18 JULY 21-31 AUGUST 5-7 (2 nights/3 days) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Boho Vintage Box Car Utopia

Escape to a one-of-a-kind retreat in a beautifully renovated 2-bedroom vintage boxcar with a private hot tub. High speed internet available for entertainment or a work vacation. Located on Rustic Roots Farm & Eco-Retreat just 1 hr north of Toronto. Explore 64 acres of trails, relax by the spring-fed pond, enjoy bonfires, or fish along the winding Nottawasaga River. With organic gardens, wildlife, and birdwatching all around, it’s the perfect place to slow down and reconnect.

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.

Lakefront Cottage | Sandy Shore, Hot Tub & Dock

Luxury lakefront cottage on beautiful Lake Simcoe with a rare shallow sandy-bottom waterfront, perfect for swimming and families. Relax in the hot tub and enjoy spectacular sunset views from the private dock. Ideal for family vacations and group getaways near Toronto, minutes from Hwy 404. Enjoy kayaking, paddleboarding, fishing, BBQ, a fire pit, 6 bedrooms, 4 bathrooms, a chef's kitchen, and bright open-concept living. Peaceful, private, and close to town.

Amazing Lake-Front Retreat w/ Hot Tub + WOW Views!

HIGHLIGHTS: - Priceless lake views that changes every day - Amazing wineries, Niagara attractions nearby - Hot tub - Lake access - Kayaks to explore the lake - Deck with BBQ - Putting green - Luxury boat rental to cruise the lake - Smart TVs (Netflix included) - Ping pong, air hockey - Clean linens, towels + surfaces disinfected to ensure guests have a clean and comfortable stay ** Please review the "Other details to note" section prior to booking **