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Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

Guests agree: these stays are highly rated for location, cleanliness and more.

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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-Salem
4.98 out of 5 average rating, 261 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

Top guest favourite
Tiny home in Wellesley
4.99 out of 5 average rating, 145 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
4.92 out of 5 average rating, 214 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
Guest house in Shakespeare
5 out of 5 average rating, 60 reviews

Cozy country getaway -clawfoot tub & starry nights

Escape to our peaceful 2-bedroom country guest house, nestled among beautiful farmland with stunning views. A tranquil retreat or a base to explore the nearby Stratford area, this modern farmhouse-style suite is the perfect getaway for up to 4 guests. Relax in a cozy yet spacious setting featuring two queen beds, an electric fireplace, and a walk-in shower with a luxurious soaker tub. Enjoy the quiet of the countryside with an outdoor fire pit and BBQ. Washer and dryer and Wi-Fi are included.

Superhost
Home in St. Jacobs
4.89 out of 5 average rating, 103 reviews

Boho 3-Bed House Retreat: HotTub, Sauna Oasis &Spa

Experience luxury in this tranquil full house in Saint Jacobs village, set on a fully fenced acre lot for privacy. It features three bedrooms: 1 king, 1queen, and a child’s bed, plus a home office. The house includes two living rooms, two full bathrooms, and a well-equipped kitchen. Highlight is the retreat oasis with a hot tub, sauna, and outdoor shower. Enjoy spa-like bathrooms with rain showers and a private outdoor patio. Nearby dining and entertainment enhance your rejuvenating getaway!

Top guest favourite
Cottage in Stratford
5 out of 5 average rating, 148 reviews

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

Beautifully renovated 1200 sq ft farmhouse just 7 minutes from downtown Stratford — perfect for theatre trips, family getaways, and weekends with friends. Sleeps up to 8 guests with 2 king beds, 1 queen, and a pop-up sofa bed. Enjoy bright gathering spaces, games, patio dining, and cozy evenings after exploring Stratford’s theatres, cafés, shops, and restaurants. For select stays, guests may enjoy a complimentary local welcome treat featuring bakery items, wine, or other local favourites.

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, 137 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.

Guest favourite
A spacious lawn is framed by birch trees, showcasing a hammock and a small table set with chairs. A cozy cabin is visible in the background, nestled among greenery and offering a serene retreat from the surrounding landscape.
Cabin in Lakeside
4.85 out of 5 average rating, 40 reviews

Cozy Cabin. Think glamping, with a few perks.

Are you looking for a peaceful getaway in the country? Our cozy cabin rental offers a serene setting surrounded by beautiful birch & pine trees, on a scenic country road. This is simple living at its best. Think glamping - but with perks. With Wildwood Conservation Area and Wildwood Lake just 200 meters away, you'll have easy access to many outdoor activities. Explore the biking trails, hike along the Avon trail, go fishing, kayaking, and revel in the natural beauty surrounding you.

Guest favourite
The exterior of the guest house features a modern facade with a mix of brown and beige siding. Double glass doors lead into the entrance, flanked by tall potted plants. Lush greenery surrounds the property, creating a welcoming approach.
Guest house in Saint Marys
5 out of 5 average rating, 50 reviews

Private Guest House

Welcome to Wellington Street Guest House, a modern and charming retreat in picturesque St. Marys, Ontario, Canada. Newly renovated and elegantly decorated, our guest house offers the perfect blend of comfort and sophistication. Whether you're visiting our historic town for a peaceful getaway, as a wedding guest or on a business trip, we look forward to making your stay unforgettable. Indulge in our meticulously designed bachelor-style suite that epitomizes comfort and style.

Top guest favourite
An expansive terrace showcases a wooden deck, bordered by a sleek railing. The sunset paints the sky with warm hues of orange and pink, illuminating the lush greenery in the distance, providing a serene backdrop for relaxation and enjoying nature.
Place to stay in Embro
4.97 out of 5 average rating, 68 reviews

Harrington View

Old world charm is felt the moment you arrive on the property.  This loft is situated in an 1897 manse.  A subtle blending of antique furnishings and modern amenities. Expect to find all the comforts of home. Beautiful stained glass windows from the original era of the home integrated perfectly into this peaceful space. With its incredible penthouse views it is a perfect location to use as a home base for exploring. Only 15 minutes from the Stratford Festival.

Guest favourite
Tiny home in Granton
4.95 out of 5 average rating, 20 reviews

Smith's Den @ Smithden

Looking for northern ambience in a weekend getaway to relax and recharge, that won’t take hours to get to? Want to spend your time vacationing not commuting? Come enjoy a private, secluded, quiet getaway! Featuring miles of maintained walking trails, two ponds and a river running through with towering pines and gorgeous natural beauty, it’s a nature lovers paradise. It is now winter here! The trails are perfect for snowshoeing or cross-country skiing.

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, 196 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

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