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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, 118 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.

Oct 10 – 17

G$42,671 GYD per night

Cottage in Wasaga Beach

4.93 out of 5 average rating, 190 reviews

Charming riverside cottage, walk to beach

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!

Nov 24 – Dec 1

G$73,960 GYD per night

Cottage in Georgina

4.98 out of 5 average rating, 132 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.

Oct 23 – 30

G$35,310 GYD per night

Cottage in Innisfil

4.9 out of 5 average rating, 290 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!

May 16 – 23

G$57,399 GYD per night

Cottage in Wasaga Beach

4.89 out of 5 average rating, 205 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

Aug 7 – 14

G$76,715 GYD per night

Cottage in Innisfil

4.99 out of 5 average rating, 121 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

Feb 19 – 26

G$140,244 GYD per night

Cottage in Innisfil

4.94 out of 5 average rating, 151 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.

Nov 24 – Dec 1

G$71,235 GYD per night

Cottage in Innisfil

4.83 out of 5 average rating, 241 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.

Sep 19 – 26

G$35,804 GYD per night

Cottage in Georgina

4.97 out of 5 average rating, 125 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.

Jan 16 – 23

G$148,989 GYD per night

Cottage in Innisfil

4.91 out of 5 average rating, 128 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.

Nov 30 – Dec 7

G$78,622 GYD per night

Cottage in Richmond Hill

4.95 out of 5 average rating, 128 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

Oct 12 – 19

G$56,372 GYD per night

Cottage in Georgina

4.9 out of 5 average rating, 239 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 ***

Sep 24 – Oct 1

G$149,677 GYD per night

Vacation rentals for every style

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Unique stays

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Popular amenities for Keswick, Georgina cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Kawartha Lakes

4.88 out of 5 average rating, 180 reviews

Waterfront ★ Hot Tub ★ Sauna ★ BBQ ★ Kayaks ★ Wifi

Apr 18 – 25

G$67,994 GYD per night

Cottage in Innisfil

4.86 out of 5 average rating, 83 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

May 9 – 16

G$68,034 GYD per night

Cottage in Georgina

4.76 out of 5 average rating, 54 reviews

Lakeside Charm: Renovated 4BR Cottage near Toronto

Jan 11 – 18

G$44,663 GYD per night

Cottage in Innisfil

4.86 out of 5 average rating, 74 reviews

Hot Tub / BANYA / Sauna - True Cottage experience

Jan 23 – 30

G$34,821 GYD per night

Cottage in Kawartha Lakes

4.83 out of 5 average rating, 29 reviews

2BR/1BA Oasis | Stylish Retreat w/Modern Amenities

Jun 4 – 11

G$36,008 GYD per night

Cottage in Innisfil

4.93 out of 5 average rating, 41 reviews

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

Sep 9 – 16

G$93,286 GYD per night

Cottage in Kirkfield

5.0 out of 5 average rating, 75 reviews

Brookside on Balsam. Rest.Relax.Restore.

Oct 16 – 23

G$51,824 GYD per night

Cottage in Kawartha Lakes

4.95 out of 5 average rating, 21 reviews

Gallery on the Lake

Sep 2 – 9

G$111,023 GYD per night

Pet-friendly cottage rentals

Cottage in Kirkfield

4.93 out of 5 average rating, 148 reviews

Balsam Lake fully renovated 4BR 2BA modern cottage

Oct 28 – Nov 4

G$87,945 GYD per night

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

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

Jun 10 – 17

G$63,021 GYD per night

Cottage in Kawartha Lakes

4.97 out of 5 average rating, 155 reviews

Balsam Brilliance, Modern Lake Home.

Mar 17 – 24

G$48,632 GYD per night

Cottage in Kawartha Lakes

4.9 out of 5 average rating, 107 reviews

1950's Romantic & Whimsical cottage on Gull River

Oct 19 – 26

G$59,294 GYD per night

Cottage in Kirkfield

4.83 out of 5 average rating, 112 reviews

Beautiful 4 Bedroom Waterfront Cottage

Oct 29 – Nov 5

G$61,890 GYD per night

Cottage in Georgina

4.96 out of 5 average rating, 57 reviews

Resort-Style Luxury Waterfront Cottage

Mar 25 – Apr 1

G$119,584 GYD per night

Cottage in Georgina

4.8 out of 5 average rating, 10 reviews

Private Luxurious Lake Simcoe Cottage

May 10 – 17

G$118,381 GYD per night

Cottage in Caesarea

4.94 out of 5 average rating, 17 reviews

Lakeside Cottage Getaway South Shore Lake Scugog

May 17 – 24

G$32,319 GYD per night

Private cottage rentals

Cottage in Wasaga Beach

4.96 out of 5 average rating, 135 reviews

Sanablue by the Bay -Stylishly Untrendy since 1958

Jul 24 – 31

G$28,901 GYD per night

Cottage in Palgrave

4.99 out of 5 average rating, 200 reviews

Hockley valley, up country guest cottage

Dec 30 – Jan 6

G$37,934 GYD per night

Cottage in Brechin

4.96 out of 5 average rating, 134 reviews

Spacious waterfront cottage w/ spectacular sunsets

Sep 23 – 30

G$63,235 GYD per night

Cottage in Keswick

4.91 out of 5 average rating, 32 reviews

Private lakefront cottage of Lake Simcoe

Jul 14 – 21

G$55,548 GYD per night

Cottage in Georgina

4.88 out of 5 average rating, 25 reviews

Cheerful 2-bdrm cottage 2 minute walk to the lake

Jan 26 – Feb 2

G$37,300 GYD per night

Cottage in Georgina

4.81 out of 5 average rating, 68 reviews

Cheerful and by the Water 4 Bedroom Cottage

Sep 4 – 11

G$56,994 GYD per night

Cottage in Mulmur

5.0 out of 5 average rating, 43 reviews

The Squire's Cottage

May 22 – 29

G$17,263 GYD per night

Cottage in Orillia

5.0 out of 5 average rating, 12 reviews

Luxury lakefront cottage escape

Apr 10 – 17

G$63,697 GYD per night

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
G$4,178 GYD before taxes and fees

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