Holiday rentals in Cook&#x27;s Bay

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 385 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...

4.87 out of 5 average rating, 144 reviews

Cottage in Georgina

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

4.77 out of 5 average rating, 328 reviews

Guest suite in Innisfil

SummerFun1bdrm+ Pass3Beach@Innis Beach+boat access

Covid19 Clean with Sanitation station set up in main entrance - Come stay at this brand new all-season, private & modern guest suite close to all Innisfil has to offer! 1.2 km away from Lake Simcoe, Big Cedar Golf Course & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

4.92 out of 5 average rating, 141 reviews

Flat in Innisfil

Ravine 2 Bedroom separate entrance basement apt

Newly finished modern walkout basement apartment in Innisfil with large windows flooding the space with natural light. Beautiful quiet ravine and private backyard. Short drive to the beach. 2 bedrooms+den, 2 queen size beds, and just about everything you need for a comfortable stay. This property has a fully equipped kitchen, laundry area, and free Wi-Fi/Netflix available on a large size flat screen TV. Two free parking spaces.BBQ $$.( Laundry is included free of charge with 2 night’s stay).

4.97 out of 5 average rating, 197 reviews

Dome in Utopia

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, Ontario. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (seasonal), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

5 out of 5 average rating, 147 reviews

Apartment in Innisfil

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

4.99 out of 5 average rating, 163 reviews

Cottage in Georgina

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.

4.91 out of 5 average rating, 275 reviews

Home in Georgina

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

Escape to this stunning vacation home, Professionally landscaped with an open-concept design, this spacious home easily accommodates large groups. Enjoy S/W views with breathtaking 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. Search "Beach House-S/W Exposure " for more info on both of our properties!...

4.88 out of 5 average rating, 150 reviews

Cabin in Georgina

Romantic Cabin N the Woods just 80km from CN Tower

This Romantic 1 bedroom Rustic Cabin was resurrected from the original homestead to re-invent this Cabin just for Couples! Birthdays, Anniversaries, Honeymoons & Proposals! Sleep under 2 -4’ huge Skylights watching the moon as it crosses directly overhead in the Loft Bedroom! 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 ( Brown Hill Tract)

4.9 out of 5 average rating, 229 reviews

Dome in East Gwillimbury

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

4.83 out of 5 average rating, 225 reviews

Cottage in Innisfil

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

4.89 out of 5 average rating, 220 reviews

Flat in Innisfil

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)

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Other great holiday rentals in Cook's Bay

Cottage in Innisfil

4.83 out of 5 average rating, 107 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

KimberlyRating, 5 stars1 week ago

Our group of seven really enjoyed our stay here. Hosts were super communicative and helpful when we had questions, and even allowed us to check in a couple of hours early upon request. The home itself was clean, in a great location on the water, and had everything we needed for our stay - including the kitchen, which was stocked with all of the cooking tools and utensils we needed for the weekend. Area is super peaceful, and with tons of amenities on the property, we practically lived outside for the weekend. Would recommend a stay here, especially for a larger group. Thank you Weiqi and Shuyan for a great stay!

5 out of 5 average rating, 77 reviews

Flat in Innisfil

Spacious Apartment 5 Minute Walk to Innisfil Beach

LindsayRating, 5 stars1 week ago

This has been hands down the best Airbnb we have ever stayed at. Dawn and Rob have truly thought of everything to make the space feel like home! They were very quick to respond to questions and had great recommendations for the area. The entire place was well stocked with everything you could think of including board games, cookware and much more. We will definitely be back!

5 out of 5 average rating, 5 reviews

Bungalow in Georgina

Dave & Jenny’s Apartment.

JyotikaRating, 5 stars1 week ago

We had a wonderful stay! Everything was clean, well-maintained, and just perfect. We really enjoyed our time here. The hosts were kind, responsive, and made us feel completely at home. The backyard was so cool and beautiful — it really added to the experience. Would definitely love to come back again!

4.97 out of 5 average rating, 98 reviews

Guest suite in Innisfil

Cozy Lakeside Couples Suite Steps From The Beach!

ColemanRating, 5 stars5 months ago

A perfect Air BnB for a getaway weekend!

4.76 out of 5 average rating, 83 reviews

Cottage in Georgina

Spacious Lakeside Cottage for Families & Groups

AadhithyaRating, 5 stars1 month ago

Had a great time and memories at Soheil' s place. he was very responsive and a great host!! one of the ceiling fan in the main bedroom wasn't working and he was quick to help us with alternate. it felt like home, check in and check out process was hassle free. little disappointed that the Jacuzzi wasn't working. overall, it was worth and a perfect weekend get away for our group. gave the proper small town vibe!!!

4.95 out of 5 average rating, 40 reviews

Guest house in Georgina

Bright & Modern Lower Level Apt in Keswick

EmilyRating, 5 stars2 weeks ago

We had a wonderful stay! Extremely clean, comfortable and spacious. Fully equipped kitchen with everything you would need. Very responsive host. Highly recommend!