Holiday rentals in Lakeside

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Top-rated holiday rentals in Lakeside

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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

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.

FamilyLocationBreakfast

5.0 out of 5 average rating, 121 reviews

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

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

LocationFamilyCleanliness

4.92 out of 5 average rating, 231 reviews

Top guest favourite

Flat in London

Modern Guest Suite with Private Entrance

Welcome and enjoy your stay in London's most desired quiet neighborhood. We have a spacious Walkout basement with a private entrance and Lockbox for self check-in and check-out. Minutes away from amenities like Tim Hortons, Bus stop, YMCA, Maisonville Shopping Mall and trails. 10 minutes drive to Western University/Fanshawe College and 15 minutes to London's Downtown or Airport. Need a hot drink, we offer a Keurig coffee maker with complimentary coffee pods, kettle, tea, sugar and sweetener.

FamilyValueCheck-in

4.96 out of 5 average rating, 168 reviews

Top guest favourite

A cozy seating area features a sleek gray couch adorned with black velvet pillows. A stylish lamp stands beside the couch, casting a warm glow. A piece of artwork depicting a cityscape is showcased on the wall, complementing the modern aesthetic.

Home in Stratford

4-Bedroom House,1 block from Lake

**BOOKMARK url: https://airbnb.ca/h/LindaStratford Licensed operation by the City (#2024-001); 4-bedroom 3-bathroom single detached brick house; Completely renovated, 2200 sqft modern vibe ; Spacious living space on main floor; Full-equipped kitchen and main floor laundry; 4 pristine bedrooms on second floor; Chic kids' game area on the loft; Large porch and rear patio; Prime location on the esteemed Elizabeth St, just one block from the Lake; Walking distance to theatres and downtown core;

LocationFamilyCheckout

4.97 out of 5 average rating, 117 reviews

Top guest favourite

Cottage in Stratford

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.

FamilyLocationSleep quality

5.0 out of 5 average rating, 159 reviews

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.

Apartment in St. Marys

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.

FamilyLocationCleanliness

4.87 out of 5 average rating, 107 reviews

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

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.

FamilyLocationQuiet

4.88 out of 5 average rating, 51 reviews

Top guest favourite

A spacious living area features a green velvet sofa with a decorative pillow, a vintage trunk serving as a coffee table, and an ornate gold mirror. Natural light filters through tall windows adorned with flowing curtains, enhancing the room's classic charm.

Flat in Stratford

GG’s Place | Character | Steps to Downtown

A charming queen bedroom apartment flooded with natural light and a simple yet chic design to accent the character and historic elements of the space. Fully equipped kitchen and a spacious living area, the apartment is a short walk to downtown restaurants, patios, coffee & independent shops. Wander a few minutes further and you will find yourself at Stratford's picturesque Lake Victoria park. Be sure to check out Pretty Pretty Boutique Suites as well! www.airbnb.ca/h/prettypretty

FamilyValueHospitality

4.98 out of 5 average rating, 277 reviews

Top guest favourite

A bright and inviting living area features a cozy sectional sofa with decorative pillows, positioned beside a well-lit kitchen with modern appliances. Large windows allow natural light to fill the space, highlighting the warm wood flooring and contemporary furnishings.

Guest suite in Stratford

Spacious Suite • Short drive to Downtown/Festivals

Minutes from the Stratford Festival and direct down Huron St. to the downtown core, this private two-level guest suite offers a quiet, comfortable retreat with easy access to theatres, restaurants, grocery stores and shops. Ideal for festival-goers, weekend getaways, and longer stays. Enjoy self check-in with private keyless entry and convenient free parking. Guests love the High Speed Fibre Optic internet (551 MBPS), the well equipped eat-in kitchen, and the quiet backyard patio.

ValueFamilyEV charging

4.97 out of 5 average rating, 430 reviews

Top guest favourite

Flat in St. Marys

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.

FamilyValueCheckout

4.95 out of 5 average rating, 77 reviews

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

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.

LocationHospitalityGetting around

4.97 out of 5 average rating, 70 reviews

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

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.

ValueLocationBiking

4.99 out of 5 average rating, 210 reviews