Cottage holiday rentals in Keswick

Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

4.89 out of 5 average rating, 205 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

.🧘 Relaxing, Quiet, waterfront property with stunning nature. 🧖‍♀️ Experience a private Spa with year round new sauna & new hot tub and amazing view. Please bring your own bath towels! 🤫 A peaceful oasis for families. Please describe your family before requesting to book. Max 6 guests incl children. Absolutely no events, parties, noise allowed. Not for a group of friends 🏖50’x302’ lot, private dock, gazebo 👩🏻‍💻65” smart 4K UHD TV, fast / reliable internet, LCD fridge, filtered water

4.89 out of 5 average rating, 194 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

4.97 out of 5 average rating, 125 reviews

A spacious living area is highlighted by a large white stone fireplace, surrounded by comfortable seating. Natural light filters through sheer curtains, enhancing the warm atmosphere. A flat-screen television is mounted above the fireplace, and a wooden dining table sits elegantly in the foreground.

Cottage in Tiny

Summer Getaway - 3 min walk to Beach, Clean & Cozy

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

A circular patio area features a fire pit at the center, surrounded by eight colorful Muskoka chairs in red and blue. The setting overlooks a serene lake and wooden dock, with a guitar resting nearby on the lawn, framed by a clear blue sky and scattered clouds.

4.91 out of 5 average rating, 294 reviews

Luxury Waterfront Cottage Hot Tub & Amazing Sunset

Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

4.94 out of 5 average rating, 279 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

4.85 out of 5 average rating, 251 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

4.95 out of 5 average rating, 124 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!

A serene lake view captures twilight colors reflected on the calm surface of the water. Soft pastel hues of pink, purple, and orange fill the sky, while the silhouette of trees frames the horizon, adding to the peaceful ambiance of the lakefront.

4.99 out of 5 average rating, 181 reviews

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for your bicycles.

4.88 out of 5 average rating, 307 reviews

An inviting exterior of a single-story cottage is depicted, featuring a patio area with a table and chairs. A green umbrella provides shade, while landscaped garden beds and a pathway enhance the setting amidst lush greenery and a clear sky.

Cottage in Wasaga Beach

Cozy Riverfront Cottage with Dock

Escape to our cozy waterfront cottage on the Nottawasaga River in Wasaga Beach! This bright, airy retreat comfortably sleeps 4 and features a large private dock and fire pit both overlooking the river plus modern amenities, outdoor dining area and BBQ. Enjoy direct river access from the dock for fishing and boating. Perfectly located just minutes from the main Beach 1 and a short drive to Blue Mountain Ski Resort, Collingwood, Creemore and the Wasaga Casino. Your ideal getaway awaits!

The exterior of the cottage displays a modern architectural design with large floor-to-ceiling windows, allowing for ample natural light. A spacious wooden deck surrounds the front, featuring lush greenery and vibrant flowers, creating an inviting atmosphere for relaxation.

4.87 out of 5 average rating, 356 reviews

Crystal Beach Cottage & Spa

**New Boat Launch 2026 In front Of Property** Serene lakefront cottage with breathtaking views! This cottage fronts on the East side & faces West for a mesmerizing sunrise & sunset. A few steps to the lake for a dip in the lake, sun bathing, paddle boarding (4 paddle boards) or a stroll up Innisfil Beach Park for a walk. An outdoor fire pit, sauna and hot tub awaits you at to relax and loosen up those muscles & release tension. A wonderful experience awaits you!

4.93 out of 5 average rating, 105 reviews

The living area features a plush blue sofa paired with a modern coffee table, creating a comfortable seating arrangement. Large windows offer views of the lake, allowing natural light to fill the space. Simple decor elements enhance the inviting environment.

Cottage in Sebright

Private Lakefront Cottage | Fishing, Canoe & Sauna

Wake up to sparkling Lake Dalrymple views at our private lakefront cottage, just 1.5 hours from Toronto ☀️🌊 Swim, canoe, fish from the dock, BBQ, or relax by the water. After a lake day, enjoy the outdoor barrel sauna 🧖‍♂️ or gather by the lakeside firepit 🔥 for sunsets, s’mores, and stargazing ✨ Inside features AC, a full kitchen, Netflix, games, record player, and stunning lake views. Perfect for couples & families seeking a fun, relaxing summer escape.

4.96 out of 5 average rating, 122 reviews

The exterior of a two-story log cabin is illuminated at night, showcasing its natural wood finish and gabled roof. A welcoming entryway features a wooden staircase leading to the front door. Surrounding green grass provides an open space, enhancing the rustic charm.

Cottage in Gilford

Lake simcoe Waterfront Log Cabin near Toronto

*Great for ice fishing on lake Simcoe* Some of the best ice fishing in Ontario, lots of Jumbo Perch, trout, whitefish etc Relax with the whole family at this peaceful place to stay. This two story, modern cottage built entirely of logs and situated on Lake Simcoe is the perfect getaway. Whether you are in the mood for entertainment, adventure, or simple relaxation, this cabin can provide you a comfortable and picturesque stay throughout your visit.

Popular amenities for cottage rentals in Keswick

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.

4.9 out of 5 average rating, 267 reviews

Utopia villa and spa

4.9 out of 5 average rating, 41 reviews

Lake Simcoe Luxury Farmhouse-Chickens-12ft Hot Tub

A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.

4.87 out of 5 average rating, 159 reviews

Spacious family cottage 45 mins from GTA!

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A large island with bar seating is positioned centrally, complemented by stylish pendant lighting. The space is illuminated by recessed lighting and features a potted plant, contributing to a contemporary atmosphere.

4.9 out of 5 average rating, 154 reviews

Hot tub, Sauna, fire pit, EV charger plug, generac

The exterior of the Lake House is surrounded by lush trees, with a wide wooden dock extending into the calm waters. A patio area features multiple red Muskoka chairs, inviting relaxation by the water's edge. Soft evening light hints at the cozy ambiance of the home.

4.85 out of 5 average rating, 137 reviews

FRIEND LAKE HOUSE

5 out of 5 average rating, 46 reviews

A charming cottage is showcased with a stone facade, set against a backdrop of lush trees. A welcoming front entrance is framed by steps leading up to a porch, while a well-maintained lawn and walking paths enhance the inviting outdoor space.

Cottage in Elmvale

Lakefront Family-Friendly Cottage on Trails

A private hot tub features bubbling, clear water, surrounded by winter scenery. Snow-covered trees stand in the background, while soft blue lights illuminate the edges of the hot tub. A tranquil atmosphere is created with a seamless connection to nature.

4.92 out of 5 average rating, 123 reviews

Couples retreat w/hot tub: Romantic Getaway

4.9 out of 5 average rating, 176 reviews

Cottage in Elmvale

Orr Lake Oasis

Pet-friendly cottage rentals

Cottage in Kawartha Lakes

The inviting living area features warm wooden paneling and a stone fireplace as a central element. Comfortable sofas are arranged around a coffee table, with a decorative rug enhancing the space. Natural light is let in through nearby windows, creating a cozy atmosphere.

4.9 out of 5 average rating, 97 reviews

Waterfront Cottage with Stunning Sunsets & Hot Tub

4.87 out of 5 average rating, 115 reviews

A stone fire pit is surrounded by blue and gray chairs on a grassy area. A gazebo is located nearby on a wooden deck, with logs neatly stacked beside it. The waterfront offers expansive views of the lake, framed by trees.

Cottage in Brechin

3 Bedroom Waterfront Cottage Kawartha Lakes

4.86 out of 5 average rating, 65 reviews

A dining area features a long wooden table surrounded by six chairs, with vibrant red cushions. A vase is placed at the center of the table, and sunlight streams through a large window, illuminating the room and offering a view of the greenery outside.

Cottage in Oro Station

Farmhouse next to Bike, Hike, Ski Forest Trails

A blue canoe is positioned on the green lawn, leading towards a cottage. The cottage features a wooden exterior and a covered patio with large glass doors, providing views of the surrounding nature.

4.89 out of 5 average rating, 75 reviews

Bluebird Cottage - Lakefront - Casino

4.94 out of 5 average rating, 81 reviews

A sandy dune is shown, with tufts of grass growing from its surface. The dune rises against a backdrop of scattered clouds and a clear blue sky, representing the natural landscape near the beach.

Cottage in Tiny

The Beach House

The exterior of the cottage is depicted, featuring a covered patio area with seating and a flower bed filled with vibrant blooms. Soft lighting enhances the home's facade, while a well-maintained lawn surrounds the structure, providing a welcoming environment.

4.83 out of 5 average rating, 81 reviews

Peaceful Cottage • Close to Lake Simcoe + Fire Pit

A balcony seating area features a round table with six chairs and an additional hanging chair. The view overlooks a marina lined with boats, showcasing modern waterfront buildings against a clear blue sky.

4.87 out of 5 average rating, 60 reviews

Lake Escape Cottage

An aerial view showcases the clear blue waters of the lake, bordered by a gentle sandy beach and lush green trees. Small boats can be seen on the water, enhancing the tranquil setting of the cottage area and surrounding nature.

5 out of 5 average rating, 13 reviews

Sandy Cove Lake Simcoe

Private cottage rentals

4.98 out of 5 average rating, 55 reviews

A charming wooden house with a sloped roof is surrounded by lush green grass. The front porch features two white chairs, and a Canadian flag proudly flutters on a pole nearby. Flower beds filled with peonies and other plants add vibrant color to the scene.

Cottage in Hawkestone

Country Cottage in Lake Country

Cottage in Kawartha Lakes

A spacious lakeside property is framed by tall trees, providing shade over the well-maintained green lawn. A dock extends into the calm waters of Balsam Lake, with colorful Adirondack chairs positioned nearby. Kayaks are positioned along the shoreline, ready for water activities.

5 out of 5 average rating, 18 reviews

4 Season Waterfront Family Chalet on Balsam Lake

4.9 out of 5 average rating, 10 reviews

Private HotTub Cottage • 3BR • FirePit • BBQ

A cozy living room features a stone fireplace surrounded by a wooden mantel. A flat-screen television is mounted above the fireplace. A neutral-colored sofa sits beside a rustic coffee table. A small desk and chair are positioned against a blue accent wall.

4.81 out of 5 average rating, 54 reviews

Spacious Lake Simcoe Retreat

4.9 out of 5 average rating, 73 reviews

A modern kitchen features a large central island topped with a bowl of fruits. Blue cabinetry complements the white countertops, while pendant lights hang above. Natural light flows through windows, illuminating the space and highlighting the stainless steel appliances and charming brick wall in the background.

Cottage in Kettleby

5-BR Home Near Toronto - Large Backyard & Fire Pit

4.88 out of 5 average rating, 17 reviews

A wooden dock extends into the clear waters of Lake Simcoe, with several boats anchored nearby. The vibrant blue sky is dotted with fluffy white clouds, reflecting a serene atmosphere perfect for waterside activities.

Cottage in Brechin

Lake Bliss - waterfront cottage

4.92 out of 5 average rating, 52 reviews

The outdoor deck offers a spacious area with wooden flooring, featuring a barbecue grill and a shaded seating area under a canopy. A private pool reflects the clear blue sky, surrounded by lush greenery, providing a serene view of the backyard and nearby trees.

Cottage in Lagoon City

Amazing Pool at 4BR/3WR Cottage + Close By Beaches