Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

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Top guest favorite

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

4.97 out of 5 average rating, 367 reviews

You’re ‘Home on Huron’ | 2 levels | Private Entry

Located on the edge of Stratford on a 2 acre property with plenty of mature trees, yet steps from many amenities such as grocery stores & restaurants. Enjoy self check-in with your own private keyless entry, 2 floors of open-concept living, lots of windows & skylights to let natural light in. Guests love the High Speed Fibre Optic internet (551 MBPS). The eat-in kitchen comes well equipped. Unwind on the outdoor patio watching sunsets or stargazing. Plenty of free parking and no cleaning fees.

Top guest favorite

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 out of 5 average rating, 101 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.

Guest favorite

A luxury tent is set amongst lush greenery, featuring a wooden deck with Muskoka chairs and a private hot tub. A hammock is visible to one side, with a picnic table positioned nearby, all surrounded by trees and natural landscaping.

Farm stay in Elora

4.93 out of 5 average rating, 199 reviews

Luxury Glamping on Elora Sunflower Farm -Sunflower

Enjoy our flower farm, historic barn and natural springs. Stay in 1 of 4 luxury tents for a unique outdoor experience with personal comforts - private hot tub, foam mattress queen bed, covered deck, espresso/coffee/tea, fan, hammock and picnic table. Glamping sites are a retreat into nature with free parking and access to the sunflower fields, corn mazes and seeing the alpacas. Walk to Elora’s Riverfest concert, festivals, activities, shops, restaurants and is a 5 min drive to downtown Fergus.

Top guest favorite

A serene view of a sunset over a grassy area is captured, with the sun dipping behind distant hills. Soft clouds are visible in the sky, creating a warm atmosphere. The red cabin stands to one side, and trees frame the image, adding natural beauty to the scene.

Tiny home in Wellesley

5 out of 5 average rating, 114 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?

Top guest favorite

A modern outdoor table features a glowing fire element at its center, providing warmth and ambiance. In the foreground, three clear glasses filled with water rest on the table. Lush green trees form a serene backdrop, creating a peaceful setting.

Cottage in Stratford

5 out of 5 average rating, 107 reviews

7mins to Theatres/Dwntwn- 2Kng 1Qu, BBQ, Firepit

Welcome to our charming rural retreat, where we love hosting guests and making every stay extra special - plus we're only 7 minutes to downtown Stratford and 17mins from St. Mary's! Many years ago this is the site of the Harmony Inn - a once thriving Mill town. Today our fully renovated 1200 sq ft heritage cottage is the perfect choice for your group meetup or theatre stay. NEW for 2025!! We've updated all the furniture, bedding and decor... come check out our NEW curated designer space!

Guest favorite

The kitchen features modern appliances, including an oven and refrigerator, complemented by sleek cabinetry. A central island with a marble countertop offers additional workspace. Natural light enters through a window, highlighting the warm wooden accent wall and creating a functional and inviting cooking environment.

Home in Stratford

4.89 out of 5 average rating, 105 reviews

Stratford Festival Entire Home - Walk to theatres.

Stratford’s world class restaurants, summer patios, market-square and the theatres - all just a short stroll away! Easily enjoy all of Stratford's character from our two bedroom, two bath minimalist cozy home. From theatres, parks and weekend markets to fun pubs, fine dining, and our welcoming public spaces. Relax, explore, and enjoy. Easy day-trips your thing? We’re only a 1hr drive to Pinery Provincial Park's 10km of glorious beaches, sand dunes and sunsets on stunning Lake Huron.

Guest favorite

A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.

Home in Cambridge

4.92 out of 5 average rating, 399 reviews

"Cottage Home On The River" 1 Bedroom

Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

Top guest favorite

The exterior of a tiny home is presented, featuring large glass panels that allow natural light to fill the interior. An open door reveals a glimpse of the modern decor inside. Surrounding greenery adds to the serene atmosphere of the property.

Tiny home in Arthur

4.97 out of 5 average rating, 287 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top guest favorite

A charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.

Home in Elora

4.96 out of 5 average rating, 780 reviews

Elora Heritage House

Welcome to Elora Heritage House, where unforgettable experiences await in the heart of Elora. Built in the 19th century, our meticulously crafted home exemplifies quality and attention to detail. Discover carefully curated rooms with mid-century furniture, modern design, and a nostalgic ambiance. Nestled amidst serene trees, generous natural surroundings, world-class dining, and shops are just steps away. Embrace the essence of Elora at our cozy haven.

Top guest favorite

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, 164 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.

Top guest favorite

The exterior of a red Prairie-style granary showcases a large two-story structure with a metal roof. Colorful foliage and a variety of plants are visible in the foreground, enhancing the natural setting. Large windows and a back patio are included, inviting outdoor relaxation.

Guesthouse in Saint Marys

4.99 out of 5 average rating, 103 reviews

Red Mill Countryside Retreat

The perfect country retreat! Relax, recharge and reconnect with nature in a spacious, peaceful guest suite enjoying tranquil views and cottage feel. You might catch a misty sunrise, or star gaze on a clear night right from the comfort of your private view. Hike a creekside trail, listen to the birdsong, or cozy up to the gas fireplace. Sample handmade soaps from our farm. Explore the quaint Town of St.Marys or nearby Stratford.

Top guest favorite

A scenic view of the property is presented, featuring a charming lamp post in the foreground and a well-maintained pathway leading to the house. The exterior showcases a blend of traditional and modern architecture, surrounded by lush greenery and a carefully landscaped yard.

Guest suite in Newton

4.92 out of 5 average rating, 285 reviews

Century Home Apartment next to the G2G Trail

This rural property is a great place to relax and unwind in the heart of Amish and Mennonite country. The location is perfect for outdoor enthusiasts with the G2G hiking/biking trail literally being in the backyard. The second storey Apartment has lots of charm and character. There is ample parking and reliable wifi. The famous Anna Mae's Restaurant and the Zehr's Country Market are 1 km down the road.