Vacation rentals in Keswick, Georgina

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Top-rated vacation rentals in Keswick, Georgina

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

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Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 213 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Mar 2 – 9

G$25,009 GYD per night

Guest favorite

Guest suite in Newmarket

4.93 out of 5 average rating, 103 reviews

2 Bed-2Bath-Kitchen | Private | Family-Couple-Work

We have an ideal place for you regardless of work, pleasure, or family time. The recently renovated suite includes: - Separate keyless entry - 2 bedrooms with closets - Living room with 55" TV - Full kitchen with storage & dining - 2 full bathrooms (1 en suite) - 2 on-premises Parking - Laundry - WiFi & more FAST EV Charger-Check for availability ($15/charge) CENTRAL LOCATION! Steps to Upper Canada Mall, Groceries, Restaurants, Trails, Parks, Golf Course, Costco, Walmart, Highway, Go, & more

Sep 21 – 28

G$17,114 GYD per night

Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 190 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Sep 21 – 28

G$29,182 GYD per night

Guest favorite

Apartment in Georgina

5.0 out of 5 average rating, 5 reviews

Quiet Country Escape Close To Beach Parks And Golf

Welcome to our country retreat! Kick back and relax in this quiet very comfortable, secluded guest suite. This unit is in a stand alone uninhabited building with its own private entrance and is not shared making it 100% yours to enjoy. This private retreat is perfect for beach and water enthusiasts, cyclists, golfers, fishing & boating. Located close to all of the shorelines of Cooks Bay all the way to Sibbald Park. The ROC and many beaches and golf courses are a short bike ride or drive away!

Sep 19 – 26

G$24,146 GYD per night

Guest favorite

Guest suite in East Gwillimbury

4.92 out of 5 average rating, 370 reviews

Stylish, Modern 2nd Floor Private Apt. Quiet Area

Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

Sep 12 – 19

G$19,264 GYD per night

Guest favorite

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 7 – 14

G$35,265 GYD per night

Guest favorite

Farm stay in Essa

5.0 out of 5 average rating, 118 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Nov 4 – 11

G$35,605 GYD per night

Guest favorite

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.

Nov 1 – 8

G$131,404 GYD per night

Guest favorite

Guest suite in Georgina

4.98 out of 5 average rating, 177 reviews

"Charming Stay at Cooks Bay" Lake Simcoe Apartment

Bright and cozy basement apartment across the street from Cooks Bay, Lake Simcoe. Melanie and I live upstairs with our dog Jersey and we have fallen in love with the Georgina area. Summer or winter Cooks Bay has a lot to offer guests who like the outdoors. It is a perfect cottage like getaway yet close enough to highway 404 to be downtown Toronto in 50 mins. The best of both worlds! 20km from Upper Canada Mall 5km from highway 404 20km to downtown Sutton 65km to downtown Toronto

Apr 10 – 17

G$15,833 GYD per night

Guest favorite

Guesthouse in Newmarket

4.93 out of 5 average rating, 122 reviews

Stylish 1-Bedroom Home in the heart of Newmarket

This recently renovated unit is located walking distance from Newmarket's GO-Train, public transit, regional hospital, and Historic Main St strip. With its central location you are steps away from nature walks, hiking trails, lovely shops, great restaurants and excellent local craft breweries. Not to mention Upper Canada Mall. Nestled on a quaint street, and sitting on a half acre lot filled with old growth trees this place gives off serious cottage vibes. (But with better Wifi)

Dec 15 – 22

G$24,023 GYD per night

Guest favorite

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 ***

Apr 16 – 23

G$142,250 GYD per night

Guest favorite

Apartment in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

Oct 12 – 19

G$15,809 GYD per night