Cottage vacation rentals in Keswick, Georgina

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Popular amenities for Keswick, Georgina cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Tiny
4.95 out of 5 average rating, 227 reviews

Private 40 Acre Cottage with Hot Tub

KassandraRating, 5 stars2 months ago
We had an amazing winter stay at this cabin! While the driveway was a bit tricky due to the winter conditions, the host was extremely responsive and gave us helpful instructions to navigate it. The cabin itself was cozy and well-equipped, making it a great place to unwind after a day of skiing. We especially loved the hot tub, it was the perfect way to relax after hitting the slopes! The space is peaceful and private, and we enjoyed exploring the walking trails and the pond. The cabin was well-stocked with everything we needed, including coffee, spices, and even a Roku TV for when we wanted to unwind indoors. Overall, it was a fantastic getaway, and would visit again!
Guest favorite
A spacious backyard features a circular stone firepit surrounded by six seating chairs in varying sizes. The two-story cottage is visible in the background, illuminated warmly from within. Lush greenery and trees provide a natural backdrop, enhancing the outdoor gathering space.
Cottage in Innisfil
4.93 out of 5 average rating, 67 reviews

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

AdritaRating, 5 stars2 months ago
Very big and beautiful place! We really enjoyed our stay here, there was more than enough room for the 9 of us. Really enjoyed the hot tub as well!
Superhost
The inviting living area features warm wooden paneling and a stone fireplace as a central element. Comfortable sofas are arranged around a coffee table, with a decorative rug enhancing the space. Natural light is let in through nearby windows, creating a cozy atmosphere.
Cottage in Kawartha Lakes
4.91 out of 5 average rating, 75 reviews

Waterfront Cottage with Stunning Sunsets & Hot Tub

LuciaRating, 5 stars1 month ago
We really enjoyed our stay. The place was cozy and the kitchen was well equipped. Mattresses are very firm That may be a personal preference. If you are looking for a relaxing week or weekend this is the place. You can make a fire outside directly in front of the water. Beautiful sunset. Beaverton is 20 mins away if you want to go into town. I do recommend a stay here. You will feel refreshed.
Superhost
A spacious wooden dock extends over the water, featuring a shaded gazebo and seating area. Surrounding trees provide a lush backdrop, while various watercraft and a swing chair are visible, enhancing the outdoor space for relaxation and recreation.
Cottage in Brechin
4.77 out of 5 average rating, 137 reviews

Beautiful Four Bedroom Lagoon City Waterfront Home

EilidhRating, 5 stars7 months ago
Daniel gave a thorough intro message of specifics the day of on top of what was already so clearly laid out. The property was beautiful with access to so many activity options. House is clean and spacious. We spent a lot of time on the dock which had a great selection of furniture and sun/shade options. The beach is a close walk. We thoroughly enjoyed our weekend and will likely be back to enjoy the space again!
Superhost
A private hot tub is situated on a concrete patio, surrounded by lush green grass and colorful plants. The serene backyard features a view of the canal, with a wooden shed and a stack of firewood visible nearby. Potted plants add a charming touch to the space.
Cottage in Brechin
4.71 out of 5 average rating, 17 reviews

Bright Modern 4-bedroom cottage w/ hot tub

CarolineRating, 5 stars2 months ago
We had a wonderful time at Irina’s place! We went during a winter snowstorm and it was beautiful and cozy, and the hot tub was very refreshing. Irina ensured that the driveway was cleared before we checked in and early on our check-out day which allowed us to enter and leave with ease (which we were worried about, considering the amount of snow!). The house was the perfect amount of space for our three families which included adults, children, babies and dogs. Thank you for a lovely stay!
Guest favorite
A large inflatable duck with headphones floats in a swimming pool, surrounded by evening lighting. A covered seating area features string lights, enhancing the tranquil and fun atmosphere. The backdrop includes a well-lit house surrounded by greenery, creating a relaxing outdoor space.
Cottage in Innisfil
4.9 out of 5 average rating, 210 reviews

Utopia Villa and Spa

MahsaRating, 5 stars2 weeks ago
We had a wonderful stay at this amazing cottag. very clean and spotless. The place was well-equipped with lots of entertainment options and fun activities for everyone. One of the highlights for us was definitely the hot tub — it was such a relaxing experience, especially in the peaceful and beautiful environment. We’re already planning to come back, and next time we’ll definitely stay for more than two days to fully enjoy everything the cottage has to offer. I highly recommend this place to anyone looking for a cozy and quiet getaway. It’s the perfect spot to unwind and recharge. Thank you for such a memorable experience Shahrzad.
Superhost
Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.
Cottage in Innisfil
4.9 out of 5 average rating, 169 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

KaraRating, 5 stars1 month ago
We stayed an extended long weekend in winter in March (winter). It was a fabulous getaway. The place was clean, bright, open, and airy. We enjoyed the hot tub, sauna, and lake view. Kris was easy to communicate with and happy to help while we were there. Highly recommend.
Superhost
Cottage in Coboconk
4.85 out of 5 average rating, 55 reviews

Modern Coboconk Kawarthas Getaway with Hot Tub

SandieRating, 5 stars7 months ago
We had a great family weekend at Tedmond's cottage! We loved the property and the deck, although outside lighting maybe could have been a but brighter. Overall though, we enjoyed it! Thanks for having us!

Pet-friendly cottage rentals

Guest favorite
A spacious deck is visible, featuring a dining table and chairs, perfect for outdoor gatherings. The log cabin stands amidst trees, with a gravel path leading to it. Natural greenery surrounds the area, creating a tranquil setting.
Cottage in Tiny
4.97 out of 5 average rating, 36 reviews

2 Bedroom Plus Bunkie Woodland Beach Cottage

JenRating, 5 stars6 months ago
Our family had an enjoyable Thanksgiving weekend at Carol's property. The cabin was cozy and charming, the bunkie was super cute and the deck and fire pit were amazing spots to hang out at. It's a short walk to the water and a convenience store/lcbo. Our only issue was that we didn't stay long enough!
Superhost
A vast, serene body of water stretches out towards the horizon under a clear blue sky. The spacious deck, featuring a decorative wooden railing, offers an ideal view of the lake, enhancing the peaceful setting for relaxation.
Cottage in Brechin
4.88 out of 5 average rating, 96 reviews

3 Bedroom Waterfront Cottage Kawartha Lakes

KamalpreetRating, 5 stars1 month ago
I had a fantastic stay at this Airbnb! The lake view was absolutely stunning, making the experience even more special. The place was clean, well-maintained, and had everything I needed for a comfortable stay. The host was friendly and responsive, making the check-in process smooth and easy. I would definitely recommend this place to anyone looking for a peaceful and scenic getaway. Can’t wait to visit again!
Superhost
Cottage in Ramara Ontario
5 out of 5 average rating, 3 reviews

Blue's Wkly Getaway: Unique cottage/casino combo!

JeremyRating, 5 stars23 months ago
Stayed here while working in the area, very comfortable set up, large yard with lots of seating. Brian replys almost instantly and had all the info you will need while staying here. would definitely recommend and come back again.
Superhost
An aerial view of the cottage and surrounding outdoor space displays a well-maintained yard with a mix of grass and pathways. The deck features outdoor seating, while the surrounding greenery offers a tranquil setting. Nearby structures are visible, providing a glimpse of the quaint hamlet.
Cottage in Caesarea
4.73 out of 5 average rating, 33 reviews

Cozy Cottage @Lake Scugog *Fire Pit & Game room*

AbigailRating, 5 stars8 months ago
Our stay at Bala’s place was a fantastic experience. We were a group of 8 including 4 tween aged children. The cottage is very well located , close to Port Perry and around 45 min to Peterborough. Lots of places to visit within the Trent Severn Waterway area. Bala graciously allow us an early check-in. His place is very cute, neat, super clean and had everything we needed to prepare meals and to entertain both children and adults alike. The game room is a great addition to the cottage. Walking distance to Lake Scugog, we were able to have nice walks after a delicious BBQ dinner. The deck and the fire pit allowed us to share quality family time while enjoying nature at its best. Thank you Bala for such a warm welcome with popcorn and soda !!. We appreciated very much your always friendly and promptly response to our needs. I will definitely recommend anyone to have a great and relaxing experience at your cottage. It is worth it !
Superhost
A sandy area is featured in the foreground with several natural stones arranged in a circle. Two wooden chairs are placed under a colorful umbrella, facing the quaint cottage, which is visible in the background and surrounded by trees.
Cottage in Tiny
4.67 out of 5 average rating, 36 reviews

Gramma's Cottage : Strtt- 2025-090 Tiny, Ontario

PatriciaRating, 5 stars9 months ago
Went to James's place for some well deserved R & R and we got it. Lovely location, great swimming, the sun was shining, sand was golden, water was perfect. All the amenities we needed. Great to sit by the fire at night and enjoy the sun set. Loved the outdoor shower.
Superhost
A well-maintained backyard features a large trampoline and a pathway made of stepping stones leading to the cabin entrance. Two wooden chairs are positioned nearby, surrounded by lush green grass and trees that provide a serene atmosphere.
Cottage in Innisfil
4.64 out of 5 average rating, 22 reviews

Cozy 2 bdrm cabin steps from beach

LeeRating, 5 stars6 months ago
Second time staying at Rachel's- lovely cottage and a great location. Rachel was extremely helpful and easy to communicate with. Thanks again!
Guest favorite
The image features a dog playfully jumping in shallow water at the edge of a beach. The sun sets on the horizon, casting warm light across the sky and reflecting gently on the water's surface, creating a serene atmosphere.
Cottage in Tiny
4.87 out of 5 average rating, 45 reviews

Balm Beach Cottage: Hot Tub/GameRoom/more!

JuliaRating, 5 stars1 month ago
We really loved our stay here. We have a 6 and 2 year old and this cottage was the perfect size for the 4 of us. I like that it’s all one level, and floors are a clean hardwood. The road in front of the cottage is so quiet and feels private. A great place to kick the ball around and jump in puddles. Hot tub and games room made this place extra special. Would love to come visit in the summer, and enjoy the beach type amenities that are just a short walk away.
Guest favorite
Cottage in Kirkfield
4.93 out of 5 average rating, 194 reviews

Balsam Lake fully renovated 4BR 2BA modern cottage

JessieRating, 5 stars4 days ago
We stayed a couple of nights and our stay was exactly what we needed - a peaceful, quiet retreat in a private lake front cottage. The view is beautiful and serene. We are already looking when we may be able to return!

Private cottage rentals

Superhost
The cottage is reflected in the tranquil waters of Orr Lake, surrounded by vibrant autumn foliage. Soft lights adorn the exterior, illuminating the deck area, while a picnic table and boat are visible in the backyard, creating a serene and inviting environment.
Cottage in Elmvale
4.88 out of 5 average rating, 74 reviews

Lakefront Cedar Haven-Canoe, Kayak, 1 hr from TO

ManaliRating, 5 stars6 months ago
The cottage was lovely! We had no trouble using the kitchen, grill and firepit. We had a beautiful view of the lake, access to kayaks and a canoe, and really clean rooms and washroom. Definitely exceeded our expectations!
Top guest favorite
A wooden dock extends over the calm water, framed by trees. Two wooden chairs provide seating at the edge, overlooking the lake. In the distance, additional chairs can be seen on the dock, inviting relaxation and connection with nature.
Cottage in Sebright
4.96 out of 5 average rating, 52 reviews

Cozy cottage perfect for families and relaxation

MeghnaRating, 5 stars4 days ago
We had a fantastic stay at Jamie and Scott’s cottage! They were truly wonderful hosts—thoughtful, attentive, and made sure every little detail was taken care of. The cottage itself was spotless and cozy, with everything we needed for a comfortable and fun getaway. The collection of games they provided was impressive and kept us entertained the whole time—there was never a dull moment. Highly recommend staying here if you’re looking for a relaxing and well-equipped retreat!
Guest favorite
A serene lakeside scene captures a sunset over calm waters. A fire pit, surrounded by stones, features glowing embers. Wooden steps lead down to the water, framed by lush greenery, while the sky displays soft hues of orange and purple.
Cottage in Sebright
4.89 out of 5 average rating, 9 reviews

Sunrise sunset retreat cottage!

VarunRating, 5 stars7 months ago
Dorrie was a great communicator, always responsive and helpful throughout our short stay. The place was exactly as described, comfortable and in a great location. We had a wonderful experience!
Superhost
An outdoor seating area is visible near a tranquil lake, featuring white Adirondack chairs arranged around wooden stumps. A wooden dock extends into the water, complementing the serene landscape under a clear blue sky.
Cottage in Orillia
4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

AnnalisaRating, 5 stars31 months ago
We spent a couple of days up here, and it was as described. It took me back to my childhood! The classic “by the lake” cottage. And it is that. Complete with a breezeway with life jackets, a great dock, and of course the fantastic lake. We enjoyed a campfire, and the place had everything we needed, for meals and memories. It is a cottage though. You should expect that. It isn’t fancy, and Geoff doesn’t describe it that way. It is how he describes. Geoff is also very responsive, and when we had a question, came back right away. It was a nostalgic little getaway for us! We loved it.
Superhost
A bright living area is created with large windows allowing natural light and offering views of the serene lake. A spacious sofa is complemented by a colorful cushion. A wooden dining table is surrounded by chairs, enhancing the cozy family atmosphere.
Cottage in Orillia
4.88 out of 5 average rating, 57 reviews

Serenity on the Lake

MunemRating, 5 stars5 months ago
Loved our stay here and Sandra was super responsive the entire time. Beautiful and private space here as well. Highly recommend!
Guest favorite
The outdoor deck offers a spacious area with wooden flooring, featuring a barbecue grill and a shaded seating area under a canopy. A private pool reflects the clear blue sky, surrounded by lush greenery, providing a serene view of the backyard and nearby trees.
Cottage in Brechin
4.97 out of 5 average rating, 38 reviews

Amazing Pool at 4BR/3WR Cottage + Close By Beaches

HarrisonRating, 5 stars2 months ago
Lovely place with lots of activities for any age. Rooms were all cozy and comfy, everything was clean and there was lots of space to hang out. Would recommend!
Guest favorite
A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. Sunlight glistens on the water's surface, while tufts of grass and sparse vegetation line the edge of the beach, enhancing the serene landscape.
Cottage in Tiny
4.91 out of 5 average rating, 43 reviews

Winter lover's paradise - snowmobile, ski etc

Aline & AlissonRating, 5 stars2 months ago
Greg’s place was great for our family reunion. The house was kept warm even with winter storm outside, they had a private snow plow to clean the driveway. Driveway is big enough for 6 cars. A cozy house that we would definitely come back in a near future.
Superhost
A view of the water from a grassy area, framed by trees and a wooden fence. Stairs lead toward the waterfront, providing access to a serene lake with clear blue water under a bright sky.
Cottage in Barrie
4.83 out of 5 average rating, 60 reviews

Lake Simcoe Cottage – Private Waterfront Escape

JamesRating, 5 stars7 months ago
Beautiful views of Lake Simcoe from the cottage, great swimming and dog friendly. Water friendly footwear is ideal as the waters are rocky. Would recommend to anyone looking to escape the city! Bruce was very helpful and responded promptly when we ran out of propane.

Quick stats about cottage rentals in Keswick, Georgina

  • Total rentals

    20 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    620 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  2. Canada
  3. Ontario
  4. Georgina
  5. Keswick
  6. Cottage rentals