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Holiday houses 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 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
5.0 out of 5 average rating, 119 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.

Superhost
A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.
Villa in Cambridge
4.88 out of 5 average rating, 131 reviews

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

Top Guest favourite
The open living area features a spacious grey sectional sofa with a round coffee table, surrounded by soft area rugs. Natural light flows through the windows, highlighting the neutral-colored walls. A dining area, visible in the background, includes a wooden table and chairs.
Home in Stratford
4.88 out of 5 average rating, 195 reviews

The Birmingham House

Hello! Our home is 3 minute walk to downtown. We are close to restaurants, theaters and shops. We focus on comfort and fun with all the necessities for families, couples and solo travelers. The home offers an open living area, fully equipped kitchen, sunroom, four bedrooms and a games room. We also have a hot tub available for our guest. Free parking for up to 3 vehicles and WIFI available. We will do our best to make your stay memorable and comfortable. Please note we do not allow parties.

Top 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, 226 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
Cottage in Stratford
5.0 out of 5 average rating, 154 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.

Guest favourite
A historic limestone building is prominently displayed at the corner of a lively downtown street. Four large windows reflect the sky, while nearby vehicles and charming storefronts contribute to the vibrant community atmosphere. The scene captures a clear day with soft clouds overhead.
Condo in St. Marys
4.87 out of 5 average rating, 105 reviews

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.

Top Guest favourite
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, 338 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 favourite
A modern living space is showcased with a round dining table surrounded by green chairs. A cozy seating area features an armchair and a sleek fireplace, while large windows provide ample natural light. Artwork adorns the walls, adding character to the environment.
Condo in Stratford
4.96 out of 5 average rating, 249 reviews

River Merchant Inn Mitchell’s Mercantile Suite

Nestled on the Avon river is the Mitchell's Mercantile Suite at the River Merchant Inn & Spa. After exploring Stratford, enjoy this One-Of-A-Kind space that walks you through times past and accurately chronicles the mercantile shop uses of this heritage building. Featuring 2 bedrooms, 1 full bath and full chef's kitchen. With free designated parking nearby and private entry pin-pad lock making checking in and out a breeze. SPECIAL NOTE: Unit is on 2nd floor, stairs only (2 flights)

Top 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
4.88 out of 5 average rating, 50 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
Apartment in St. Marys
4.94 out of 5 average rating, 68 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
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, 69 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.

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, 207 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.

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