Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

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Superhost

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, 103 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 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, 206 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.

Superhost

A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.

Home in Elora

4.99 out of 5 average rating, 179 reviews

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

Superhost

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, 124 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?

Superhost

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, 113 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!

Superhost

A serene outdoor seating area features two light-colored chairs facing a small red table. Beyond lies a calm lake surrounded by trees, with a hanging ornament visible above. The ground is covered in grass, offering a peaceful spot to relax.

Cottage in New Dundee

4.88 out of 5 average rating, 215 reviews

Cozy Waterfront Cottage

Cozy waterfront cottage. Nestled in the woods on a private lane. Enjoy this cottage vacation while being only minutes from the city of Kitchener. Take in the fresh air, cast a rod in the lake, float around in a canoe, enjoy a fire under the stars, or just hang out on the deck. In winter, explore the frozen lake with skates or snowshoes. Propane fireplace is available for emergency heat only in winter. In the event of a power outage this would be the only heat available. We allow one pet.

Superhost

A welcoming living area is highlighted by a brown leather sofa and a glass coffee table with a wooden base. A cozy fireplace is flanked by ornamental decorations, while soft drapes frame a window. The floor is covered with plush, light-colored carpeting.

Apartment in Linwood

5 out of 5 average rating, 103 reviews

The Olde Chick Hatchery

Our spacious, newly updated, 3-bedroom apartment is nestled within the heart of Waterloo Region's Mennonite and Amish Community. This unique Airbnb, a former chick hatchery, is flooded with natural light, creating a warm and inviting atmosphere. Our huge rooftop patio provides a perfect spot for relaxing. Prepare delicious meals in our fully equipped kitchen. Conveniently located 10 minutes from the village of St. Jacobs, 15 minutes from Waterloo and along the Guelph to Goderich trail.

Superhost

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

4.95 out of 5 average rating, 179 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)

Superhost

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

4.93 out of 5 average rating, 405 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!

Superhost

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, 798 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.

Superhost

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, 170 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.

Superhost

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, 106 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.