Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

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Top guest favourite
A vintage schoolhouse stands in the background, showcasing its distinctive architecture and large windows. In the foreground, a well-crafted bike rack holds several bicycles under a shaded canopy, surrounded by autumn foliage and a gravel pathway.
Home in New Hamburg
5 out of 5 average rating, 108 reviews

The Heart of New Hamburg - Picturesque Modern Home

This newly renovated schoolhouse doubles as a picturesque live-in museum! Well lit with stately windows, the upper level delivers a fusion of classic and modern with a fully equipped kitchen, master bedroom and large bathroom with a quaint tub and hand crafted fittings. The lower level boasts of 2 bedrooms with bathrooms, a cozy living area, kitchenette, dedicated workspace and separate entrance. The back patio has heated flooring; making the winter months bearable for outdoor activities.

Guest favourite
The living area features a sleek black entertainment center with a large television and decorative glass display cabinets. A coffee table is positioned in front of a dark leather sofa, with warm wood flooring and exposed brick walls adding character to the space.
Apartment in Stratford
4.97 out of 5 average rating, 180 reviews

The Loft on Downie - Downtown Stratford

Located on the top floor, with a view of downtown, our 450 square foot condo is steps away from the heart of downtown Stratford and all it has to offer including cozy coffee shops, elegant restaurants, the Avon Theatre, close to the famous Stratford festival, and other shops for all to enjoy. Perfect for a couple’s getaway or to enjoy as friends travelling together. Our condo offers all the essentials including a luxurious queen bed, fully equipped kitchen, a 55” smart TV and ensuite laundry.

Top guest favourite
A single-story cottage is showcased with a light-colored exterior, surrounded by vibrant trees displaying autumn foliage. A spacious deck is visible, furnished with red Muskoka chairs and a table, providing a welcoming outdoor seating area.
Cottage in Fingal
4.98 out of 5 average rating, 128 reviews

Port Talbot Shore Stay

This completely renovated cottage at Port Talbot is on Lake Erie, just 20 minutes west of Port Stanley. It is one of 3 homes located on this 400 acre property called the Port Talbot Estates. You will have lots of privacy as each house is well spaced away from each other. This luxury cottage has it all and is steps away from a beautiful Lake Erie beach. Locally, St. Thomas and Port Stanley have plenty of shops, restaurants, bars, grocery stores, breweries and local museums for you to explore!

Top guest favourite
A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.
Home in Elora
4.99 out of 5 average rating, 241 reviews

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

Guest favourite
A small cabin with a red roof is set amidst a green lawn, surrounded by trees. A campfire pit, with smoke rising gently, is situated in front of the cabin. A rustic wooden table is nearby, enhancing the natural outdoor setting.
Tiny home in Wellesley
4.99 out of 5 average rating, 136 reviews

RUSTlC~OFFGRlD~OASlS&MlCRO-CABlN

Are you looking for a space to get away, a peaceful oasis immersed in nature? Welcome to Clemmer's Chaos Rustic Escape! It's off-grid. No electricity. No running water. No Wi-Fi. There are bugs and critters. An outhouse for your business. A Cabin for two. A Space for Tents. A mini lake. You can swim, fish, canoe. There is a campfire pit, to cook over, sing around, or listen to the soft sounds of nature and crackling fire as you stare up at the stars. This is an experience. Au Naturel. You in?

Guest favourite
A cozy living area is presented with a spacious sectional sofa, complemented by a side chair and a wooden coffee table. Minimalist decor includes potted plants and simple wall art on a shelf. Natural light enters through large windows, dressed with soft curtains.
Bungalow in Saint Marys
4.91 out of 5 average rating, 207 reviews

The Old Blue Cottage of St. Marys

Placed perfectly only a half block from the Thames River in the hidden architectural wonderland that is St Marys, Ontario is the recently renovated ‘Old Blue Cottage’. Just south of Stratford, 20 minutes northeast of London and a little under an hour’s drive from Kitchener-Waterloo you’ll find this quaint two-bedroom retreat; one featuring a bunk bed, and principle bedroom with a walkout to the covered back deck. There’s also a fold-out couch for extra guests in the great room. HST Inclusive

Top guest favourite
A repurposed shipping container is set within a forested area, surrounded by tall trees. A circular fire pit made of smooth stones can be seen in the foreground, with a fire crackling. A hammock is hung between two trees nearby, and two chairs are positioned on a wooden deck.
Shipping container in Simcoe
4.97 out of 5 average rating, 134 reviews

Little Can in the Pines - Bunkie No. 1

*NO hydro/power/electricity *NO running water *NO flush toilet (outhouse only) *NO Wi-Fi *NO street lights (it's dark at night) *NO sheets, blankets, pillows - Queen *NO cookware, plates, utensils etc. *HEATED seasonally from Oct - May *Outdoor shower - operates seasonally *Poor cell signal (except Rogers) *Very private *Far from road - 800 ft *Dogs welcome *Firewood for sale *BBQ & propane provided w/ tongs & spatula *Bunkies are 400 ft apart from each other We look forward to hosting you!

Top guest favourite
A comfortable sleeping area features a spacious bed dressed in a patterned white and gray quilt. A microwave is placed nearby, along with a decorative screen partition. The bathroom area is visible in the background, showcasing essential amenities.
Flat in Thamesford
4.96 out of 5 average rating, 319 reviews

Stay Inn Thamesford - Cozy 1 Bedroom unit/apt.

Enjoy a relaxing stay in our stylish and cozy little nook right in the hub of our friendly little town. Walking distance to Tim Horton's, RBC bank, variety stores, pizza pick up, town swimming pool, cannabis store and liquor & beer . Only 20 minutes London or Woodstock . It's important to note that our quaint unit does have a saniflo toilet and pumping system(ie. maceration system) which means there is noise associated with flushing and drainage. Please inquire if more info is needed!!

Top guest favourite
A welcoming living area is displayed with a cozy gray sofa and a bright yellow armchair. A wood-burning stove stands beside a wall-mounted television. Natural light enters through a window, illuminating the area rug and a bookshelf filled with books.
Barn in Gads Hill
5 out of 5 average rating, 129 reviews

The Country Nook

This barn style cabin is located 10 -15 minutes from Stratford, Ontario the home of Stratford Festival. This newly renovated 1.5 floor retreat offers an open concept living area, along with two bedrooms with queen size beds. Large windows and a 16 foot ceiling height in the living room add to the brightness of the space. This home away from home offers both comfortable seating inside and a screened in patio nestled into the trees. A way to get away from the city and enjoy the fresh air.

Top guest favourite
The exterior of a charming A-frame cottage showcases a triangular roof and large front deck. Colorful chairs and umbrellas are arranged on the patio, bordered by landscaped greenery. Surrounding trees provide natural shade, contributing to the serene atmosphere of the property.
Chalet in Port Stanley
4.84 out of 5 average rating, 207 reviews

The Sunset Chalet is in a Quiet neighbourhood.

WELCOME to Sunset Chalet. We have had a make over! See and hear the nature at the front and back. You may get a view of the many deer,fox and wild turkeys that frequent this quiet neighbourhood. From the hilltop you get a partial view of water and pier.Hear the fishing boats as they pass to go into Port to unload their catch (the action starts around noon). Port is full of excitement: enjoy the theatre, public library, many coffee shops, restaurants, taverns, and Beaches.

Top guest favourite
Cottage in Stratford
5 out of 5 average rating, 141 reviews

Holiday Getaway | 7mns to Dntwn | Games | Sleeps 8

March Special: Stay 2+ nights and enjoy a complimentary local bakery breakfast basket. Stay 3+ nights and we’ll include 4 Stratford Chocolate Trail passes, a self-guided tasting experience at participating downtown shops. Cozy renovated 1200sqft farmhouse just 7 minutes from downtown Stratford, ideal for March Break or group getaways. Sleeps up to 8 with 2 kings, 1 queen, and a pop-up sofa bed. Bright, comfortable space for gathering, games, and relaxed evenings together.

Top guest favourite
A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.
Cottage in St. Jacobs
4.99 out of 5 average rating, 192 reviews

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

Popular amenities for Lakeside holiday rentals

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