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Cottage vacation rentals in Keswick, Georgina

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Top-rated cottage rentals in Keswick, Georgina

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A comfortable wicker chair is positioned on a wooden deck, overlooking a lush green lawn. The view features tall trees and glimpses of Lake Simcoe in the distance, creating a serene outdoor environment.

Cottage in Brechin

4.91 out of 5 average rating, 98 reviews

Cottage on Lake Simcoe Amazing lake Views

Lovely, well maintained three bedroom, two bath cottage on a protected bay of Lake Simcoe. The cottage is located right on Lake Simcoe beside shared community park. cristal shallow water for Swim and kayak. The views are beautiful. With the property facing south enjoy plenty of sunshine from late morning to sunset. Great spot for winter fishing. Fully equipped kitchen Please note the water behind the backyard is shared by few neighbors and it’s not private , and the beach area is not private.

A wooden deck overlooks tranquil waters, featuring two red Adirondack chairs facing the lake. The beautifully colored sky at sunset casts a serene ambiance, surrounded by lush greenery and trees providing a natural frame.

Cottage in Brechin

4.92 out of 5 average rating, 159 reviews

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.

A scenic view of the lake is visible from a wooden deck, featuring large planters with colorful flowers on either side. Several Muskoka chairs are arranged on the grassy area leading to the water, where a dock is visible in the distance.

Cottage in Brechin

4.85 out of 5 average rating, 107 reviews

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.

A spacious outdoor deck is surrounded by lush greenery, providing a serene atmosphere. Comfortable seating arrangements, including a dining set, invite al fresco meals and gatherings. The natural light filters through the trees, enhancing the tranquil outdoor experience.

Cottage in Innisfil

4.95 out of 5 average rating, 102 reviews

Innisfil retreat: Hot Tub, Sauna, Game room

Welcome to our serene Lakeside Retreat in Innisfil, a haven of relaxation and fun. This getaway features a rejuvenating sauna and hot tub, perfect for unwinding after a day of adventure. Entertain with family and friends in our game room, which includes a pool table, air hockey table, and dartboard. The large outdoor deck is ideal for BBQs, complemented by a cozy fire pit for evening relaxation. The house offers five beautifully appointed bedrooms, ensuring comfort for everyone. Water softener.

A wooden dock extends into clear water, featuring vibrant red lounge chairs positioned for relaxation. The shoreline is bordered by smooth stones and gentle waves, with lush greenery in the background enhancing the natural setting.

Cottage in Kawartha Lakes

4.95 out of 5 average rating, 165 reviews

Balsam Brilliance, Modern Lake Home.

Picturesque lakehouse nestled on 370ft of prime sandy waterfront on pristine Balsam lake at the top of the Trent canal. EVERY room has breathtaking views of the water. 4 bedrooms, 2 bathrooms and large, fully stocked open-concept kitchen with upscale appliances – perfect for any large group. Excellent internet Large docks to park your boat or rent from Balsam RPM Only 1.5 hours from Toronto 5 minutes to Coboconk Note that during July and August only Friday to Friday bookings are accepted.

Top guest favorite

Cottage in Georgina

4.99 out of 5 average rating, 157 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 you bicycles.

The exterior of the cottage showcases dark siding complemented by expansive windows. A wooden deck extends from the building, featuring several lounge chairs. Surrounding trees provide a natural backdrop, creating a serene environment under clear blue skies.

Cottage in Kawartha Lakes

4.91 out of 5 average rating, 45 reviews

The Cottage in the Woods

July 2023: New Updates to furniture (inside & out) Welcome to the Cottage in the Woods located on the beautiful Four Mile Lake in Coboconk, Ontario. This beautiful newly renovated lakefront 4 season cottage offers the serenity and charm of the Kawartha Lakes and is less than 10 minutes to the quaint town of Coboconk. The cottage is 3 bedrooms, 1 bathroom. Equipped with two rooms with custom bunk beds larger than a twin that can easily accommodate 1 adult or 2 children. (Sleeps 8-10)

Cottage in Wasaga Beach

4.88 out of 5 average rating, 253 reviews

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

Top guest favorite

Cottage in Kawartha Lakes

4.9 out of 5 average rating, 117 reviews

1950's Romantic & Whimsical cottage on Gull River

My whimsical & quaint cottage is 5klm from town which hosts a Foodland, LCBO, Pub, ice cream window and Home Hardware. Balsam Lake Provincial Park and Indian Point Provincial Park are close as well. I love my cottage because of the gardens, the chandeliers, the purple doors and the glorious clean river! The cottage itself is 900sq.ft. of cuteness & the property is 100 x200sqft. Canoeing, kayaking, bbqing, swimming, snorkeling and river floating are daily activities.

A wooden dock extends towards the calm water, flanked by two red chairs positioned for lakeside relaxation. The clear water reveals a sandy bottom, while lush greenery surrounds the peaceful scene, enhancing the waterfront's tranquil atmosphere.

Cottage in Kirkfield

4.84 out of 5 average rating, 121 reviews

Beautiful 4 Bedroom Waterfront Cottage

Beautiful waterfront 4 Bedroom cottage for families and group up to 8 adults . Lot size 75 ft x 350 ft deep. The cottage is renovated in 2016 Hardwood floor through out,large modern kitchen, New Large deck with spectacular lake view. kids play ground and two fire Pit, firewood is provided. Free WiFi, BBQ, parking (6 cars) and boat docking (4 boats) . In addition, Free of use for 1 x canoe and 1 x 14 ft aluminum boat with oars 2 x kayaks and 1 x puddle boat.

Cottage in Kawartha Lakes

4.78 out of 5 average rating, 101 reviews

Serenity by the Lake: Lake Waterfront Cottage

Welcome to our delightful 3-bedroom 4 season waterfront cottage located on the beautiful Cameron Lake in Fenelon Falls, where endless aquatic adventures await! Nestled in a serene location, this picturesque retreat offers the perfect blend of comfort and natural beauty. With its prime position by the water's edge, it's an idyllic haven for swimming, boating, and fishing enthusiasts alike. Property is located only 1.5 hrs. from the GTA & directly off of HWY 35

Top guest favorite

A quaint red cottage is highlighted alongside a rustic barn, surrounded by a wooden fence. Lush greenery and wildflowers accompany the structure, creating a natural setting. The areas are bathed in warm sunlight, enhancing the serene and secluded atmosphere of the property.

Cottage in Palgrave

4.99 out of 5 average rating, 209 reviews

Hockley valley, up country guest cottage

please read the entire post our beautiful cottage is located on 27 acres of land. Which is very secluded and quiet. Open concept cottage , with a loft bedroom with a double bed, a double sofa bed and a single folding bed. Wood burning fire place and a Small area with a hot plate , microwave, toaster oven, coffee maker , small fridge , BBQ on the porch. Swimming pond Vegetable garden and honey bees. Beautiful wooded trail No smoking Kids are welcome

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Popular amenities for Keswick, Georgina cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A spacious backyard features a circular stone firepit surrounded by six seating chairs in varying sizes. The two-story cottage is visible in the background, illuminated warmly from within. Lush greenery and trees provide a natural backdrop, enhancing the outdoor gathering space.

Cottage in Innisfil

4.93 out of 5 average rating, 67 reviews

Lake View Haven Cottage W/Hot Tub - Steps to Beach

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.

Cottage in Kawartha Lakes

4.91 out of 5 average rating, 75 reviews

Waterfront Cottage with Stunning Sunsets & Hot Tub

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.

Cottage in Brechin

4.77 out of 5 average rating, 137 reviews

Beautiful Four Bedroom Lagoon City Waterfront Home

A private hot tub is situated on a concrete patio, surrounded by lush green grass and colorful plants. The serene backyard features a view of the canal, with a wooden shed and a stack of firewood visible nearby. Potted plants add a charming touch to the space.

Cottage in Brechin

4.71 out of 5 average rating, 17 reviews

Bright Modern 4-bedroom cottage w/ 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.

Cottage in Innisfil

4.9 out of 5 average rating, 211 reviews

Utopia Villa and Spa

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.

Cottage in Innisfil

4.9 out of 5 average rating, 171 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

Cottage in Coboconk

4.85 out of 5 average rating, 55 reviews

Modern Coboconk Kawarthas Getaway with Hot Tub

A lakeside view of the cottage reveals a spacious deck surrounded by trees. The calm water reflects the greenery and structure, while a sandy area is visible near the shore, providing a serene atmosphere for relaxation.

Cottage in Oro-Medonte

5 out of 5 average rating, 18 reviews

THE LAKE HOUSE WITH PRESTINE PANORAMIC VIEW!

Pet-friendly cottage rentals

A modern wood stove is positioned in the corner, providing warmth with its visible flame. Above hangs a round clock, while a black ladder rack displays a cozy blanket. A woven basket rests nearby, filled with soft pillows, contributing to a relaxing atmosphere.

Cottage in Tiny

4.87 out of 5 average rating, 38 reviews

Year Round Two Bedroom Cottage with Fireplace

A vast, serene body of water stretches out towards the horizon under a clear blue sky. The spacious deck, featuring a decorative wooden railing, offers an ideal view of the lake, enhancing the peaceful setting for relaxation.

Cottage in Brechin

4.88 out of 5 average rating, 96 reviews

3 Bedroom Waterfront Cottage Kawartha Lakes

Cottage in Ramara Ontario

5 out of 5 average rating, 3 reviews

Blue's Wkly Getaway: Unique cottage/casino combo!

Cottage in Brechin

4.94 out of 5 average rating, 31 reviews

Your cozy, by the water escape on Lake Ave awaits!

An aerial view of the cottage and surrounding outdoor space displays a well-maintained yard with a mix of grass and pathways. The deck features outdoor seating, while the surrounding greenery offers a tranquil setting. Nearby structures are visible, providing a glimpse of the quaint hamlet.

Cottage in Caesarea

4.73 out of 5 average rating, 33 reviews

Cozy Cottage @Lake Scugog *Fire Pit & Game room*

A sandy area is featured in the foreground with several natural stones arranged in a circle. Two wooden chairs are placed under a colorful umbrella, facing the quaint cottage, which is visible in the background and surrounded by trees.

Cottage in Tiny

4.67 out of 5 average rating, 36 reviews

Gramma's Cottage : Strtt- 2025-090 Tiny, Ontario

A well-maintained backyard features a large trampoline and a pathway made of stepping stones leading to the cabin entrance. Two wooden chairs are positioned nearby, surrounded by lush green grass and trees that provide a serene atmosphere.

Cottage in Innisfil

4.64 out of 5 average rating, 22 reviews

Cozy 2 bdrm cabin steps from beach

Cottage in Little Britain

4.8 out of 5 average rating, 30 reviews

Cozy Lakeview Cottage | Kawartha Lakes Getaway

Private cottage rentals

A spacious screened-in porch features a long dining table surrounded by six chairs. Large windows offer views of a serene pond and the surrounding landscape. A barbecue grill is positioned nearby, enhancing the outdoor dining experience.

Cottage in Wasaga Beach

4.96 out of 5 average rating, 271 reviews

GATED RESORT COTTAGE

The cottage is reflected in the tranquil waters of Orr Lake, surrounded by vibrant autumn foliage. Soft lights adorn the exterior, illuminating the deck area, while a picnic table and boat are visible in the backyard, creating a serene and inviting environment.

Cottage in Elmvale

4.88 out of 5 average rating, 74 reviews

Lakefront Cedar Haven-Canoe, Kayak, 1 hr from TO

Top guest favorite

A wooden dock extends over the calm water, framed by trees. Two wooden chairs provide seating at the edge, overlooking the lake. In the distance, additional chairs can be seen on the dock, inviting relaxation and connection with nature.

Cottage in Sebright

4.96 out of 5 average rating, 52 reviews

Cozy cottage perfect for families and relaxation

Cottage in Georgina

4.76 out of 5 average rating, 82 reviews

Lakeside Multi Family 4BR Cottage near Toronto

A serene lakeside scene captures a sunset over calm waters. A fire pit, surrounded by stones, features glowing embers. Wooden steps lead down to the water, framed by lush greenery, while the sky displays soft hues of orange and purple.

Cottage in Sebright

4.89 out of 5 average rating, 9 reviews

Sunrise sunset retreat cottage!

A stony beach area is shown beside a clear lake. Several white adirondack chairs are positioned around a fire pit, with a wooden structure in the background. A dock extends into the water, while trees provide shade along the shoreline.

Cottage in Orillia

4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

A serene fire pit area surrounded by wooden seating faces the calm lake, highlighted by the evening sunset. A small stone circle encloses the flickering flames, while the tranquil water reflects the soft colors of dusk. A dock and lounging area are visible in the background.

Cottage in Washago

4.83 out of 5 average rating, 77 reviews

The Crown LakeFront

Cottage in Orillia

4.88 out of 5 average rating, 57 reviews

Serenity on the Lake

Quick stats about cottage rentals in Keswick, Georgina

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
620 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore