Vacation rentals in Keswick, Georgina

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Top-rated vacation rentals in Keswick, Georgina

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Guest favorite

Guest suite in Innisfil

4.87 out of 5 average rating, 126 reviews

Open tiny king suite with semi-private waterfront

Your family will enjoy to stay in this centrally-located PET FRIENDLY SMOKE FREE place. Open concept tiny king suite semi-private waterfront. King suite is attached to family home-shared walls & locked doors. (Suite-kitchenette & laundry) Play board games inside on rainy days. Walk outside around the house to enjoy waterfront morning sunrise over lake. Pullout loveseat. All Beds in same room. Order food. Walk to beach, shopping & fast food. Drive to larger shopping centers, restaurants &more.

Guest favorite

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 294 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...

Guest favorite

Guest suite in Holland Landing

4.92 out of 5 average rating, 418 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.

Guest favorite

Cottage in Georgina

4.9 out of 5 average rating, 262 reviews

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

Escape to this stunning cottage retreat, just 7 minutes from the 404 and 45 minutes from Toronto. Professionally landscaped with an open-concept design, this spacious home easily accommodates large groups. Enjoy southwest-facing views with breathtaking sunrises and sunsets, and swim safely in the sandy-bottomed lake, 3-6 feet deep within 150 meters of shore. Nestled in a quiet neighborhood yet close to supermarkets, restaurants, and LCBO, this retreat has everything for an unforgettable stay.

Guest favorite

Cottage in Georgina

4.99 out of 5 average rating, 150 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 favorite

Farm stay in Essa

4.99 out of 5 average rating, 164 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!

Guest favorite

Cabin in Georgina

4.91 out of 5 average rating, 127 reviews

Romantic Cabin N the Woods just 80km from CN Tower

This Romantic 1bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom!We 've even had 3 marriage proposals here (She said YES!! ) or simply enjoy a time away to re-connect with your loved one! Sit under stars Year Round in the modern new Hot tub after your run or walk on 200 acres of hilly trails 5kms from the cabin.

Guest favorite

Guest suite in Schomberg

4.92 out of 5 average rating, 451 reviews

Romantic Country Suite for Couples with King Bed

Our Country Suite is all about Rustic Elegance. Come to our farm for a night, a weekend, or longer. Perfect place for a quiet, peaceful & relaxing weekend escape or a romantic getaway. You’ll love our rural location, full kitchen, wifi internet, 55" 4K Smart TV, three piece bathroom, laundry, propane BBQ, Patio access to propane fire pit. Enjoy walking trails in our bush, biking, close to nature and much more. Located about 50 min. from Toronto.

Guest favorite

Dome in East Gwillimbury

4.91 out of 5 average rating, 176 reviews

Deerleap Glamping Dome

Looking for a peaceful escape from the city? Our glamping dome offers just that, situated on 10 acres of picturesque land with trail, streams, and a stunning pond view. Perfect for a romantic retreat or a weekend getaway with the family, our dome is equipped with everything you need, from upscale sanitary to fast Wifi. Relax and enjoy the starry sky from the comfort of your bed, gather around the bonfire for s'mores , or explore nearby Lake Simcoe.

Guest favorite

Home in Innisfil

4.91 out of 5 average rating, 156 reviews

King Bed*Pool*Fireplace*BBQ*Smart TV

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen

Guest favorite

Rental unit in Gilford

4.89 out of 5 average rating, 204 reviews

Lakeside Simcoe Fisher's apartment

Enjoy the cozy attached private Fisher's apartment in the small town of Gilford. The town is surrounded by Lake Simcoe and we are right across the street from the lake. You can fish at any season and sail your boat during the summer! We are also minutes away from the Cooks Bay Marina where you can rent boats and canoes. It's a great place to enjoy it with friends and family! ( Not a lakefront home)

Guest favorite

Cabin in Innisfil

4.93 out of 5 average rating, 102 reviews

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks & grocery store Honey, our golden doodle will greet you!