Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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Top guest favorite
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 favorite
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.
Condo 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 favorite
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 favorite
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, 242 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 favorite
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 favorite
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

Superhost
A geodesic dome features a spacious sleeping area with a large bed adorned in neutral tones and textured pillows. Large windows surround the space, offering views of the outdoors, while a cozy seating area contains a dark armchair and a small dining table for two.
Dome in Goderich
4.86 out of 5 average rating, 286 reviews

Glamping plus, lake front, hot tub, private

We have created a very unique getaway a long the shores of Lake Huron. In combining glamping and romance you will be able to enjoy the number one rated sunsets of Lake Huron. Whether it be from your private deck barbecuing, having a campfire, or relaxing in your own hot tub we offer the chance to disconnect and reconnect. A bunky with 4 bunk beds is included should you choose to use it. Bring your hiking boots or snow shoes and check out the near by trails! Private beach access steps away!

Top guest favorite
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.
Apartment 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 favorite
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 favorite
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 favorite
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.

Top guest favorite
A cottage is surrounded by vibrant red foliage, showcasing a blend of natural colors. The exterior features light wood siding and a tiled roof, with large glass doors leading to a patio area. Lattice work adorns parts of the structure, adding texture and visual interest.
Guesthouse in Delhi
4.98 out of 5 average rating, 169 reviews

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

Popular amenities for Lakeside vacation rentals

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  2. Canada
  3. Ontario
  4. Oxford County
  5. Lakeside