Cottage vacation 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.

4.88 out of 5 average rating, 194 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

The cottage exterior is illuminated under the evening sky, with a new hot tub positioned on a stone patio. A staircase leads to the entrance, and warm light can be seen through the windows, suggesting a cozy atmosphere inside.

4.84 out of 5 average rating, 380 reviews

Cabin retreat with hot tub & trails near the beach

Beautiful, modern, pet-friendly cottage nestled in the trees. Located on a large, private lot secluded at the end of a small gravel road. The huge yard backs onto a forest with an extensive trail network meandering a peaceful river steps from your backdoor. Mapleview beach is a short walk down the road along with many other scenic beaches in the area. The cottage is warm, cozy and fully equipped. Offering high-speed internet and smart TVs, brand new hot tub, BBQ, outdoor firepit, and boardgames.

4.88 out of 5 average rating, 170 reviews

Cottage in Keswick

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.

4.95 out of 5 average rating, 121 reviews

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

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!

4.94 out of 5 average rating, 136 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

4.99 out of 5 average rating, 170 reviews

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.

Cottage in Keswick

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 you bicycles.

4.9 out of 5 average rating, 241 reviews

Utopia villa and spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

The exterior of a two-story cottage is shown, featuring a large front porch and a combination of light gray siding with darker trim. A spacious driveway leads to a double garage, and the fenced backyard is visible behind the house. Green grass and trees enhance the setting.

4.83 out of 5 average rating, 315 reviews

6 Bedroom Cottage near Lake & Innisfil Beach Park.

Gorgeous 6 Bedroom Executive Cottage - "Special weekly, monthly, and Winter Discount 20-35%" Short walk to Lake Simcoe, Innisfil Beach Park, Public Beach, Fishing Dock & Boat Launch, winter & summer activity, Ice Fishing. Close to Friday Harbor all Season Resort, many Golf Courses, Sunset Speedway, Innisfil Arena & OLG Slots, short walk to Grocery, LCBO, Pizza Pizza, Tim Horton, Subway Sandwich & Restaurants. Ample Parking. Guest must be 25 years or older in order to book this properly.

4.92 out of 5 average rating, 107 reviews

Couples retreat w/hot tub: Romantic Getaway

Escape to tranquility in this spacious, serene home, now offered at an affordable rate for couples seeking a private retreat. Enjoy exclusive access to the entire property. Nestled along a canal leading to Lake Simcoe, this stunning home features a fully-equipped kitchen, outdoor BBQ, and a cozy firepit. Unwind in your private hot tub overlooking the water, or relax in the comfortable living and dining area. With fast Wi-Fi and beautiful surroundings, it's the perfect romantic getaway.

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.

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.

4.88 out of 5 average rating, 296 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 Retreat with Dock / Ski

→Bright, 2 bedroom cottage with 1 queen, 1 twin bunk bed →Comfortably sleeps up to four →Fantastic views up and down the Nottawasaga River →Air conditioning, Firepit →9 Minutes to the NEW Wasaga Beach Casino →Great fishing (Steelhead, trout, pike, salmon, bass, pickerel), boating, canoeing, kayaking →Central to skiing - Blue Mountain, Mount St Louis Moonstone, Horseshoe →Large Dock on the Nottawasaga river →On-premise parking for up to 3 vehicles →High-Speed unlimited internet

4.96 out of 5 average rating, 109 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 Keswick cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A wooden dock extends into calm, clear water, featuring four colorful chairs in red and yellow. The boat is partially visible at the edge, and a tree-lined shore is seen in the distance under a bright blue sky filled with fluffy clouds.

4.81 out of 5 average rating, 16 reviews

charming Lakefront Cottage with Hot Tub

4.93 out of 5 average rating, 15 reviews

The cottage exterior is shown, featuring dark blue siding and well-maintained flower boxes beneath the windows. A stone pathway leads to wooden steps, and a grassy area surrounds the house, complemented by hedges providing privacy. The sky is clear, suggesting a bright day.

Cottage in Beaverton

Cozy 4-Bedroom Waterfront Cottage in Beaverton

4.9 out of 5 average rating, 96 reviews

A spacious cottage is surrounded by neatly manicured lawns and lush greenery. The exterior features a large deck with railings, offering views of the landscape. Tall trees and shrubs contribute to a serene outdoor environment.

Cottage in Midhurst

Circle Pine Getaway Private Modern Cottage Living

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, 87 reviews

Waterfront Cottage with Stunning Sunsets & Hot Tub

Four white Adirondack chairs are positioned on a pebble beach, facing a calm lake. A wooden dock extends into the water under a bright blue sky, while the sun reflects off the surface, creating a serene atmosphere.

4.85 out of 5 average rating, 26 reviews

Family cottage just steps away from Lake Simcoe

4.96 out of 5 average rating, 53 reviews

An aerial view showcases a serene property nestled among lush greenery, featuring a spacious lawn dotted with trees and a small dock by the water. A charming glass cabin is visible near the water's edge, alongside a gathering area with outdoor seating.

Cottage in Beaverton

Your River-Side Getaway

4.84 out of 5 average rating, 19 reviews

Cottage in Georgina

Luxury Farmhouse retreat,12ft Hot Tub- Lake Simcoe

4.91 out of 5 average rating, 132 reviews

Innisfil retreat:Hot Tub, Sauna, fire pit

Pet-friendly cottage rentals

4.86 out of 5 average rating, 64 reviews

An open-concept living area features a spacious sectional sofa and a wooden dining table surrounded by white chairs. Bright lighting illuminates the room, highlighting the modern kitchen with sleek cabinetry and stainless appliances. Large windows allow natural light to enhance the inviting atmosphere.

Cottage in Sutton

Cozy 4 Bdr Cottage Near Lake Simcoe & Beaches

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.

4.87 out of 5 average rating, 112 reviews

3 Bedroom Waterfront Cottage Kawartha Lakes

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.

4.79 out of 5 average rating, 66 reviews

Peaceful Cottage • Walk to Lake Simcoe + Fire Pit

4.69 out of 5 average rating, 48 reviews

A tranquil view of Lake Simcoe at sunset is captured, showcasing shimmering golden reflections on the water. The horizon stretches into the distance, framed by lush greenery and smooth stones along the shoreline.

Cottage in Keswick

Cottage at Lake Simcoe

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

A cabin is presented with a gray exterior and steps leading to the front door. In the foreground, there is a colorful decorative bird statue on a tree stump, with a trampoline visible to the side. Surrounding greenery contributes to a natural atmosphere.

4.7 out of 5 average rating, 27 reviews

Cozy 2 bdrm cabin steps from beach

5 out of 5 average rating, 58 reviews

The open concept living area features a warm wood ceiling and a mix of comfortable seating, including leather sofas and a plush red chair. A handcrafted wooden coffee table sits centrally, while the staircase leads to additional bright spaces. Large windows provide natural light.

Cottage in Gilford

Welcome to "R" Cottage

A stone fire pit area is surrounded by multiple dark blue chairs, positioned for comfort and conversation. Mature trees provide shade, with a serene view of the water in the background, reflecting the sky's colors. The scene invites relaxation and outdoor gatherings.

5 out of 5 average rating, 14 reviews

Lake Simcoe Beachfront Cottage

Private cottage rentals

4.98 out of 5 average rating, 42 reviews

A modern living area is equipped with a gas fireplace and a mounted flat-screen TV. Comfortable seating arrangements include two armchairs and a sofa. Natural light filters through multiple windows, illuminating a wooden coffee table placed on a patterned area rug.

Cottage in Wasaga Beach

4 Season Fun! /Winter Fest/Getaway

A spacious wooden dock extends over the water, featuring a shaded gazebo and seating area. Surrounding trees provide a lush backdrop, while various watercraft and a swing chair are visible, enhancing the outdoor space for relaxation and recreation.

4.76 out of 5 average rating, 144 reviews

Beautiful Four Bedroom Lagoon City Waterfront Home

4.85 out of 5 average rating, 62 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 rustic bar area features wooden shelves displaying vintage memorabilia. High-backed stools surround a counter, complemented by a circular glass table. Natural light enters through large windows, illuminating the space, while decorative signs adorn the walls, adding character to the inviting atmosphere.

4.95 out of 5 average rating, 21 reviews

Lakeside Fall retreat at the Venice of Ontario

4.96 out of 5 average rating, 57 reviews

A gravel driveway leads to a welcoming cottage surrounded by greenery. A wooden fence, marked with the number 311, encloses the front yard. The home features a modest exterior with large windows, shaded by tall trees. Parking space is visible nearby.

Cottage in Wasaga Beach

Wasaga Beach Retreat on the Water

The living area is highlighted by large triangular windows allowing natural light to fill the space. A grand piano sits beside a plush sofa, complementing the wooden flooring. A coffee table is positioned in front of the sofa, with greenery adding a touch of nature.

4.67 out of 5 average rating, 63 reviews

Friday Harbour Ice Fishing Getaway

The exterior of a spacious two-story home is presented, featuring a combination of stone and siding. Large windows reflect natural light, and an outdoor seating area under an umbrella invites relaxation. A well-maintained lawn with shrubs and seasonal foliage enhances the curb appeal.

4.92 out of 5 average rating, 38 reviews

All Season Cozy Cottage Lake Simcoe Orillia

A two-story cottage features a light gray exterior with a white railing surrounding a spacious balcony. A large, round umbrella provides shade over outdoor seating, while vibrant greenery and floral details adorn the front yard. A dark garage door is visible beneath the balcony.