Holiday rentals in Lakeside Beach

4.96 out of 5 average rating, 142 reviews

Guest house in Uxbridge

Guesthouse in nature mins to Durham trails & Spa!

Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Cabin in Whitchurch-Stouffville

4.99 out of 5 average rating, 102 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

4.98 out of 5 average rating, 555 reviews

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Guest suite in Port Perry

4.88 out of 5 average rating, 208 reviews

Sunset Haven

Cozy suite, this location provides the very best of the outdoors for cottaging enthusiasts 45 minutes from the GTA. Found on the outskirts of Port Perry near the Blue Heron Casino and on the shores of Lake Scugog, you will find great fishing, swimming, and boating at your doorstep. Also great lounging on the deck/dock! The casino is 5 min drive and the town of Port Perry with its good restaurants and shopping is 10 min car ride or take your boat! Unfortunately, no pets are allowed by guests.

4.97 out of 5 average rating, 105 reviews

Flat in Port Perry

Romantic & Cozy Countryside luxury loft with views

Romance in the Country. Getaway from the hustle with your sweetheart, to play, rest/work stay-cation. Newly built, equip’d kitchen, bath/laundry/EV charger. Pro- designed for peaceful time away. Great trails, theatre, shopping in quaint downtown Port Perry, boating, golfing, equestrian farm, museums, & amazing 5 star restaurnts in Port Perry. Enjoy the pond on the property & lots of places to enjoy peace & quiet together! 1 hr from TO, 8 min to Port Perry. We have 2 rms king/queen bedrms.

4.97 out of 5 average rating, 179 reviews

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

4.92 out of 5 average rating, 609 reviews

Dome in Port Perry

South Geodome - Birchwood Luxury Camping

Located one hour from Toronto, Birchwood is a luxury camping experience for two. Immersed in a private forest on Scugog Island, our geodesic dome allows for a cozy and relaxing getaway. Enjoy the surrounding landscape and check out local shops and restaurants on Port Perry main street. Our geodome is designed for 2 guests however small families of 4 or a group 3 adults are welcome. Additional guests must be 12+ and added to your reservation at the time of booking. We do not allow pets.

4.99 out of 5 average rating, 122 reviews

Island in Lakefield

Suite Island Retreat

We invite you to relax and recharge with this unique island glamping experience; a tiny lakefront cabin with modern touches. From your private dock, swim in the deep water, play on the floaty mat, lounge, read, paddle in the canoe, and catch -both- a sunrise and a sunset… absolute perfection. Amenities also include an outdoor kitchen and BBQ, a fire pit, an outdoor shower, and a clean and airy outhouse. Oh, and a lovely hammock, made for two! Come and enjoy! :) -Minimum 3 nights-

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.

4.96 out of 5 average rating, 485 reviews

Cabin in Lakefield

The Nook, Peaceful Retreat: Lake+Hot Tub+ Sauna!

Heritage barn turned zen-den! Our open-concept, loft style, timber-frame cabin has exposed beams, barn board walls, and plenty of windows to enjoy the lake view. Decorated with a beachy boho meets mid-century vibe, it's cozy and airy at the same time! The private deck offers the perfect place to listen to the birds and read a good book. The Nook is on our 1 acre, lakefront property, alongside our home. We hope you love it here as much as we do!

4.98 out of 5 average rating, 160 reviews

Flat in Port Perry

Lake Brews

Welcome to Lake brews, where we are passionate about providing an unprecedented level of hospitality and accommodations for our guests. We love to travel, just like you, and we have drawn from all of our experiences from our stays at resorts around the world in order to create a truly memorable experience for you, here, on Lake Scugog, just an hour drive from the GTA.

4.82 out of 5 average rating, 135 reviews

Tiny home in Clarington

A Tiny Getaway

Discover the charm of our Tiny House! Parked beside a scenic farmer's field, this 8x21 ft. tiny house on wheels boasts a whimsical 1959 GMC pickup up front, creating a unique and cozy atmosphere. Enjoy stunning sunsets, tranquil rain nights, and the best of tiny living. Located in Orono, you're close to local attractions. Experience the magic – book your stay now!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Lakeside Beach holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Lakeside Beach

Holiday home in Port Perry

4.95 out of 5 average rating, 21 reviews

Contemporary A Frame on Scugog Island with Pool

SusanRating, 5 stars10 months ago

This was our second time staying at the property and it was just as beautiful as the first time. Our family enjoyed the pool and all the amenities offered by the house made us feel very comfortable and right at home. Would recommend for families looking to enjoy some relaxation in peaceful surroundings with all the comforts of home. Thank you for your wonderful hospitality!

4.99 out of 5 average rating, 78 reviews

Tiny home in Millbrook

Pinecrest Forest Cabin

ReannaRating, 5 stars1 week ago

We had a perfect relaxing weekend at Jen and Chad’s cabin! The cabin has windows on every wall and all you can see is trees when you look outside. It was cozy but spacious inside, spotless throughout and the bed was very comfortable. The kitchen has everything you need and we used the bbq for our dinners. The cabin is steps from the Millbrook Valley Trails. Jen and Chad have a handy map of the trails in the cabin along with menus and recommendations for local spots. We can’t wait to return for a cold weather getaway!

Dome in Port Hope

4.79 out of 5 average rating, 213 reviews

Foxberry Domes - Evergreen | unique glamping stay

ChristineRating, 5 stars3 weeks ago

We had a fantastic stay at Samantha and Jesse's. The instructions were clear, the setting was beautiful and it was very comfortable and serene. We'll definitely be back!

4.89 out of 5 average rating, 75 reviews

Home in Oshawa

Cozy Basement Suite in Oshawa

GordRating, 5 stars5 days ago

Abby is very nice, easy to communicate with, and was very accommodating with parking my large truck. Check in was a breeze. Her place is clean, private and safe. The bed was very comfortable as well. It shows that she puts a lot of care into her space. I couldn’t be happier with my stay and would highly recommend.

4.72 out of 5 average rating, 36 reviews

Cottage in Caesarea

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

AllisonRating, 5 stars2 weeks ago

Absolutely amazing! We had a fantastic stay over the weekend. Bala responded right away to any questions we had. He was very descriptive with instructions and made sure to include all that we needed to do in detail. It was very clean! The kitchen provided everything we needed. Bala also provided some extra towels for our stay which was very nice and thoughtful. We would 100% recommend staying here!

4.92 out of 5 average rating, 39 reviews

Cottage in Innisfil

Lakefront Luxury with Private Dock

RobinRating, 5 stars3 months ago

This place is extraordinary! Beautiful space to be in with a great bit of lake to enjoy. Would highly recommend, and hope to return myself some day.

4.98 out of 5 average rating, 41 reviews

Dome in Tay

The Secret Garden - Dome Escape

IsabellaRating, 5 stars3 days ago

My boyfriend and I decided to have a 1 night get away at the secret dome and it was absolutely amazing. Deborah was the best Airbnb host I have ever met, she was so sweet and responsive. She went above and beyond with getting us gifts, snack basket, and decorations for our anniversary and my birthday coming up. It was a pleasure being able to spend the weekend there and I would absolutely do it again. Her animals are also so adorable and we got to feed them! 100% recommend for a nice private and peaceful getaway and the photos don’t do it justice with how nice it is there.