
Holiday rentals in Lakeside
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Top-rated holiday rentals in Lakeside
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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

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?

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

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.

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.

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.

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.

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.

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.

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.

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.

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
Other great holiday rentals in Lakeside

Stylish Private Loft | 1800s Farmhouse | Lake View

Harrington View

Country Oasis Accessible Retreat

Luxury Hayloft Near Turkey Point and Port Dover

Modern Downtown Suite | King Bed | The Charlotte

Private Riverside Cabin

The Penrose | Two-Bedroom Suite | King and 2 Twins

lost + found under the pines
Destinations to explore
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- Grand Bend Beach
- Pinery Provincial Park
- Elora Gorge
- Port Stanley Beach
- Western University
- Boler Mountain
- University of Waterloo
- Wilfrid Laurier University
- Victoria Park
- University of Guelph
- St Jacob's Farmer's Market
- Museum
- Waterloo Park
- Budweiser Gardens
- Elora Quarry Conservation Area
- Conestoga College
- Dark Horse Estate Winery Inc.
- Cambridge Butterfly Conservatory
- Emerald Lake
- Turkey Point Provincial Park
- Stratford Festival
- Springbank Park
- Kitchener Farmers' Market
- The Factory





