Holiday rentals in Lakeside

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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

Boho 4-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, 2 single beds, Double Bed with 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!

Downtown Views, Two Bedroom Condo with Kitchen

Perfect space for families visiting loved ones or the working professional. Located in the heart of downtown St. Mary's, is a luxury two bedroom condo with 12 foot ceilings, four huge windows with stunning views of downtown in a historic limestone building. Experience all that St. Marys has to offer, steps away from charming downtown shops, beautiful walking trails, and the scenic Little Falls. Only a 20 minute drive to Stratford, home of the Stratford Festival and wonderful culinary scene.

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.

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.

Stylish Private Loft | 1800s Farmhouse | Lake View

One-of-a-kind loft that sits inside a restored 1800s farmhouse with exposed beams, gas fireplace, and a sunroom with serene water view. Separate entrance, completely private unit — designed for the ideal getaway. King Endy bed with luxe cotton bedding, roomy bathroom with soaker tub. Nespresso, craft teas, induction stove. Hi-fi sound system, 55" 4K TV with Netflix and Prime. Sit/stand desk with Herman Miller chair. Minutes from the highway — peaceful, private, and unforgettable.

Charming St. Mary's Retreat

Discover the enchanting village of St. Mary's, where this newly constructed rental awaits your arrival. An exquisite blend of modern luxury and small-town charm, this property is just a leisurely stroll from the vibrant heart of the town, picturesque trails, and delightful shops that invite exploration. Whether you are visiting for the renowned Stratford Festival or simply seeking a romantic weekend getaway, this elegant sanctuary is the perfect home base for your adventures.

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.

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.

The Penrose | Two-Bedroom Suite | 2 Kings

Offering a stay that feels more like refined living, our two bedroom suite features plush king size beds and blackout drapery. Complete with a luxurious velvet sleeper sofa and a cast-stone surround gas fireplace, the spacious living area is perfect for social gatherings and those late-night conversations. Awaken to the serene call of nature and step out onto the expansive private veranda, where sweeping views of the golf course valley unfold before you.

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.