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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 gray sofa facing a stone fireplace. A wooden coffee table sits atop a patterned rug, surrounded by two black chairs. Warm lighting creates a welcoming ambiance, complemented by wooden flooring and light walls.
Guest suite in East Zorra-Tavistock
4.92 out of 5 average rating, 102 reviews

Quaint Rural 2-Bedroom Oasis

The whole group will be comfortable in this spacious and unique property. Located between Woodstock and Stratford, very private with 1900 sqft of stylish decor and complete with a kitchen, living space and a games room. Terra Nova Nordic Spa is located directly beside rental. At evening, you can enjoy a campfire outside with lots of seating area and a private patio. Also available outside is a large hot tub with condition’s. We are a 2 night stay If considering a 1 night stay See other details

Top guest favourite
Tiny home in Wellesley
4.99 out of 5 average rating, 150 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 St. Marys
4.92 out of 5 average rating, 218 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

Guest favourite
Farm stay in Strathroy
4.95 out of 5 average rating, 38 reviews

Off-grid greenhouse cabin nestled in the woods

Sleep in a glass greenhouse under the stars. The Starhouse is a unique stay tucked into a quiet forest on our working organic farm. Discover a place to slow down, wake to birdsong, and experience some magic. Spend your mornings with coffee in the sunlight, your evenings by the fire, and your days wandering the gardens, meeting the chickens, and gathering food from our farm for dinner under the open sky. This is a simple, off-grid experience that is grounding and deeply connected to nature.

Top guest favourite
Guest house in Shakespeare
5.0 out of 5 average rating, 65 reviews

Cozy modern country getaway-Minutes from Stratford

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.

Top guest favourite
Cottage in Stratford
5.0 out of 5 average rating, 150 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
5.0 out of 5 average rating, 139 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
The exterior view showcases a two-story home with a combination of brick and stone accents. A well-maintained driveway leads to a parked vehicle, while large, arched windows allow natural light to brighten the entrance. The front porch features elegant columns, contributing to the home's welcoming appearance.
Guest suite in London
4.92 out of 5 average rating, 268 reviews

Modern Cozy Executive Suite with Private Entrance

Forget your worries in this spacious and serene space. Welcome to our cozy centrally located basement unit with a separate private entrance. This place is just 2-5 minutes away from walmart supercentre, No Frills Grocery, Winners, Homesense, Marshalls, the University Teaching Hosipital, the University of Western Ontario and many other places. The stylish unit is perfect for working individuals, and people seeking a comfortable private and convenient stay in a beautiful neighborhood.

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, 41 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.

Top guest favourite
Flat in St. Marys
4.94 out of 5 average rating, 51 reviews

The Loft @ 162 Queen • Walk Downtown + Parking

Step into a light-filled heritage loft in the heart of downtown St. Marys. Built in 1855, this charming second-floor apartment blends original hardwood floors, soaring ceilings, and large heritage windows with modern comfort. Enjoy your morning coffee in the sunlit window seats, then step outside to restaurants, coffee shops, shops, trails, and essentials just steps away. This is the only downtown short-term rental with direct downtown access and private onsite parking.

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, 200 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.

Guest favourite
Tiny home in Granton
4.95 out of 5 average rating, 22 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. In winter the trails are perfect for snowshoeing or cross-country skiing.

Popular amenities for Lakeside holiday rentals

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