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, 201 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, 186 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.

4.85 out of 5 average rating, 124 reviews

A serene lake view is captured at sunset, with vibrant colors reflecting off the calm water. A firepit sits in the foreground, surrounded by stone edging. In the background, a dock and deck extend into the lake, framed by trees on the shoreline.

Cottage in Brechin

Lakefront Cottage with Gorgeous Sunset Views

Cozy cottage with gorgeous views right on the lake. Perfect lake for water play, great fishing right off the dock, plenty of nature trails and boat launch nearby. Enjoy your evenings as you take in the sunset around 1 of 2 firepits, whether you choose to have a fire right at the water's edge or up top. There is also a boathouse you can relax on top of under the shade of the trees. Enjoy eating outside on the oversized deck as you take in the views of the lake. Lots of outdoor space to play.

4.9 out of 5 average rating, 259 reviews

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.

Cottage in Alcona

Utopia villa and spa

Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

4.94 out of 5 average rating, 275 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!

4.95 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!

4.98 out of 5 average rating, 124 reviews

Cottage in Kirkfield

Brookside on Balsam. Rest.Relax.Restore.

Clean, modern, open concept, vaulted ceilings, chef's kitchen views. 2 bedrooms with additional sleeping space on lower level. 2 separate bathrooms include soaker style tub and walk in tiled shower. Nature abounds! A charming brook, lakeside views, swimming, BBQ, outdoor dining, firepit** fire ban for April** year-round hot tub. Bicycles, kayaks and snow shoes are yours depending on the season. Short walk to Balsam Lake Provincial Park. Minutes to village shopping. Consistent Super Host!

4.88 out of 5 average rating, 304 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!

4.99 out of 5 average rating, 179 reviews

The living area features large windows that offer views of the expansive lawn. A wooden coffee table is centered between a floral-patterned couch and a comfortable armchair. Light wood flooring complements the cozy atmosphere of the room.

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.

4.91 out of 5 average rating, 290 reviews

Cottage in Keswick

Sunset Luxury Lakehouse | Private Beach & Hot Tub

Luxury Lakefront Estate | Private Beach | Stunning Sunsets Experience the perfect group getaway in this 3,500 sqft, 6BR/4BA retreat. Featuring: 🌊 PRIVATE SANDY BEACH: Shallow entry, kayaks, SUP & Lily Pad included. ✨ RELAXATION: Lakeside Hot Tub, 3 Fireplace lounges & Sunset Gazebo. 🍽️ GOURMET LIVING: Lakeview kitchen + 14-seat grand dining table. 🎮 FUN: Dedicated game room, firepit & kids' sand play area. Only 50 mins from Toronto. Perfect for families and large reunions!

4.97 out of 5 average rating, 119 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.

4.85 out of 5 average rating, 248 reviews

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

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

Popular amenities for cottage rentals in Keswick

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.94 out of 5 average rating, 16 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

Cottage in East Gwillimbury

The image captures a serene sunset over the water, with vibrant orange and yellow hues reflecting on the surface. A dock extends into the water, accompanied by gentle silhouettes of trees along the bank. The scene conveys a sense of tranquility at day's end.

5 out of 5 average rating, 8 reviews

Watrfrt Cottage | Sunset Views & 45 Min to Toronto

The exterior of a modern cottage is framed by autumn-colored trees, showcasing a combination of natural stone and wood finishes. Well-maintained landscaping with low hedges leads to a welcoming entrance. A backyard fire pit with seating is positioned on the right, surrounded by fallen leaves.

4.97 out of 5 average rating, 65 reviews

Beautiful Luxury Cottage in Kawartha Lake…

4.91 out of 5 average rating, 32 reviews

Cottage in Georgina

Affordable Cottage Getaway, W/ Year-Round Hot Tub

4.9 out of 5 average rating, 69 reviews

A living room boasts a large stone fireplace and a flat-screen television displaying a warm fire. The high ceiling features large windows offering lake views. A cozy armchair is positioned nearby, and a decorated Christmas tree adds a festive touch to the space.

Cottage in Hawkestone

All Season Cottage Water Front On Lake Simcoe

4.97 out of 5 average rating, 91 reviews

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

An aerial view captures the serene setting of the property, surrounded by vibrant greenery. Tall trees create a natural canopy over the spacious lawn, enhancing the sense of privacy and tranquility. A gravel driveway leads up to the home, merging seamlessly with the lush landscape.

4.9 out of 5 average rating, 149 reviews

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

4.93 out of 5 average rating, 72 reviews

The image captures a wooden dock extending into a serene lake, surrounded by lush greenery. Two white structures are visible in the background, along with a dome tent. Red Adirondack chairs are arranged on the grassy shore, creating a welcoming outdoor space.

Cottage in Port Perry

5-Acre Waterfront Cottage w/sauna & Hot Tub

Pet-friendly cottage rentals

A serene view overlooking Cameron Lake is captured, showcasing calm waters under a vast sky with fluffy white clouds. A wooden dock extends into the lake, with a bright orange life ring positioned at the end, providing a touch of color against the tranquil landscape.

4.79 out of 5 average rating, 117 reviews

Serenity by the Lake: Lake Waterfront Cottage

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, 64 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

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.

4.82 out of 5 average rating, 76 reviews

Peaceful Cottage • Close to Lake Simcoe + Fire Pit

The exterior of a quaint cottage features a welcoming porch area with a set of chairs and a table. Flower pots enhance the environment, while the charming purple door adds a whimsical touch. The surrounding natural landscape includes grassy areas and scattered stones.

4.9 out of 5 average rating, 127 reviews

1950's Romantic & Whimsical cottage on Gull River

5 out of 5 average rating, 13 reviews

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.

Cottage in Orillia

Sandy Cove Lake Simcoe

5 out of 5 average rating, 32 reviews

Cottage in Caesarea

Lakefront Cottage + Boathouse & Sunsets

4.7 out of 5 average rating, 27 reviews

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.

Cottage in Alcona

Cozy 2 bdrm cabin steps from beach

Private cottage rentals

4.92 out of 5 average rating, 63 reviews

Cottage in Tiny

A modern retreat on Georgian Bay STRTT-2026-089

4.74 out of 5 average rating, 78 reviews

The setting sun casts a warm glow over the calm waters of Canal Lake, with reflected hues of orange and gold creating a tranquil view. Silhouetted trees line the horizon, enhancing the serene atmosphere of the waterfront.

Cottage in Kirkfield

Waterfront Cottage on Canal Lake (Kawartha's)

4.95 out of 5 average rating, 21 reviews

Cottage in Kirkfield

West Corner Lakefront Cottage

4.93 out of 5 average rating, 97 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

Lakefront Sauna Winter Escape

4.94 out of 5 average rating, 80 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 living area features a spacious sectional sofa accented with decorative cushions. A large television is mounted on the wall, while a glass coffee table sits on a textured rug. Natural light filters in through the window, offering a bright and inviting atmosphere.

4.92 out of 5 average rating, 79 reviews

Stunning Sunset Lakehouse | Dual WiFi/BBQ/Family

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, 53 reviews

Spacious Lake Simcoe Retreat