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Cottage vacation rentals in Keswick, Georgina

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Top-rated cottage rentals in Keswick, Georgina

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Cottage in Brechin

4.96 out of 5 average rating, 121 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.

Guest favourite

Cottage in Georgina

4.99 out of 5 average rating, 139 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.

Guest favourite

Cottage in Innisfil

4.9 out of 5 average rating, 294 reviews

Crystal Beach Cottage & Spa

Tranquil & 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 or a stroll up Innisfil Beach Park for exercise. A custom outdoor steel fire place and an all season hot tub awaits you at any moment to loosen up those muscles & release tension or kick back in the sauna to sooth the mind, body & soul. A wonderful experience awaits you!

Guest favourite

Cottage in Wasaga Beach

4.89 out of 5 average rating, 210 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

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

Guest favourite

Cottage in Innisfil

4.98 out of 5 average rating, 124 reviews

Charming waterfront cottage on Lake Simcoe

Charming four-bedroom cottage plus Boat house conveniently located 1 hour from GTA on a private waterfront lot surrounded by mature trees with sandy bottom and clear water. The proximity of the cottage to the water is sure to please either the sun or shade lovers with multiple large decks and dock for sitting, dining and lounging. We offer hot tub, Sauna, BBQ. trampoline, bball net, paddle boat, floating mat, kayaks, canoe, paddle board, pool table, foosball. fishing gear, life jackets

Cottage in Innisfil

4.84 out of 5 average rating, 250 reviews

Cozy cottage nestled in the forest, near the beach

Beautiful, modern, cottage-like home nestled in the trees. Located on a large and extremely private property at the end of a small gravel road with no neighbours on one side. Huge yard backs onto a forest with trails leaving your doorstep. Mapleview beach is only a short walk to the bottom of the road and there are so many other scenic beaches in the Sandy Cove area. The home is fully equipped, clean and cozy, with high speed internet and smart TVs, comfy bedding and pillowtop mattress.

Guest favourite

Cottage in Innisfil

4.94 out of 5 average rating, 156 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.

Guest favourite

Cottage in Georgina

4.97 out of 5 average rating, 129 reviews

Pearl by Lake Simcoe - with sauna and steam room

Spacious and bright newly renovated house with access to the lake. This 2700 sqf house has a very functional and beautifully decorated living/dining area, 2 state of the art kitchens, 6 cosy bedrooms and 3 full washrooms. Huge 400 sqf deck with BBQ and heater comfortably fits a large company outside. Enjoy indoor sauna and steam room for deep relaxation. Free Wifi. Large entertainment room with Smart TV, XBox, Kinect and a foosball table provide plenty of activities inside the house.

Guest favourite

Cottage in Innisfil

4.89 out of 5 average rating, 132 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 🤫 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, all high tech.

Guest favourite

Cottage in Richmond Hill

4.95 out of 5 average rating, 129 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Guest favourite

Cottage in Georgina

4.9 out of 5 average rating, 243 reviews

Beach House-S/W Exposure! Hot Tub Sandy Water!

Location, Location, Location! S/W Exposure! firepit, hot tub, west-facing sunset views, fishing, swimming, boating, and nearby amenities. In winter, it transforms into a winter wonderland, perfect for ice fishing and snowmobiling. New renovated 4-seasons retreat. Less than an hour from the GTA. This lakeside haven on Prestigious Cooks Bay provides the ideal getaway. Enjoy a rejuvenating experience with a *** Don't miss out on this incredible opportunity ***

Guest favourite

Cottage in Palgrave

4.99 out of 5 average rating, 200 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

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Keswick, Georgina cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Wasaga Beach

4.93 out of 5 average rating, 192 reviews

Charming riverside cottage, walk to beach

Cottage in Georgina

4.75 out of 5 average rating, 57 reviews

Lakeside Multi Family 4BR Cottage near Toronto

Cottage in Innisfil

4.87 out of 5 average rating, 77 reviews

Hot Tub / BANYA / Sauna - True Cottage experience

Cottage in Innisfil

4.86 out of 5 average rating, 83 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Guest favourite

Cottage in Kirkfield

5.0 out of 5 average rating, 77 reviews

Brookside on Balsam. Rest.Relax.Restore.

Cottage in Orillia

4.9 out of 5 average rating, 21 reviews

Family cottage just steps away from Lake Simcoe

Cottage in Innisfil

4.88 out of 5 average rating, 42 reviews

Oasis with HotTub steps from Friday Harbour Resort

Guest favourite

Cottage in Innisfil

4.93 out of 5 average rating, 46 reviews

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

Pet-friendly cottage rentals

Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 110 reviews

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

Guest favourite

Cottage in Georgina

4.97 out of 5 average rating, 60 reviews

Resort-Style Luxury Waterfront Cottage

Cottage in Innisfil

4.76 out of 5 average rating, 17 reviews

Amazing Cottage Close to beautiful lake Simcoe

Cottage in Georgina

4.8 out of 5 average rating, 15 reviews

Georgina Waterfront Cottage w/ game room

Cottage in Innisfil

4.92 out of 5 average rating, 38 reviews

Lake Side Manor With Games Room

Cottage in Innisfil

4.85 out of 5 average rating, 62 reviews

Hinnisfil Lakehouse - Cheerful 3 bedroom cottage

Guest favourite

Cottage in Innisfil

4.99 out of 5 average rating, 95 reviews

❤️ Charming Cottage/Lake View/10PPL/5BDR/3BATH

Guest favourite

Cottage in Brechin

4.89 out of 5 average rating, 76 reviews

Cottage on Lake Simcoe Amazing lake Views

Private cottage rentals

Guest favourite

Cottage in Brechin

4.96 out of 5 average rating, 134 reviews

Spacious waterfront cottage w/ spectacular sunsets

Guest favourite

Cottage in Wasaga Beach

4.96 out of 5 average rating, 136 reviews

Sanablue by the Bay -Stylishly Untrendy since 1958

Guest favourite

Cottage in Keswick

4.91 out of 5 average rating, 32 reviews

Private lakefront cottage of Lake Simcoe

Guest favourite

Cottage in Georgina

4.88 out of 5 average rating, 25 reviews

Cheerful 2-bdrm cottage 2 minute walk to the lake

Cottage in Georgina

4.81 out of 5 average rating, 68 reviews

Cheerful and by the Water 4 Bedroom Cottage

Guest favourite

Cottage in Georgina

4.81 out of 5 average rating, 53 reviews

Lakefront and Riverview Cottage

Cottage in Georgina

4.82 out of 5 average rating, 17 reviews

Cozy Lakefront Cottage

Guest favourite

Cottage in Tiny

4.98 out of 5 average rating, 43 reviews

Edmore Cottage at Tiny Beaches

Quick stats about cottage rentals in Keswick, Georgina

Total rentals
10 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
530 reviews
Nightly prices starting at
$27 CAD before taxes and fees

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