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Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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, 108 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.

Top guest favorite
A dining table is featured with a round glass top, complemented by modern white chairs. A decorative planter with an artificial orchid sits at the center, next to a wooden coaster inscribed with 'The Danny'. Natural light enters through a nearby window.
Home in Stratford
4.99 out of 5 average rating, 268 reviews

The Danny - A Unique Stratford Beauty.

The Danny is a beautiful HOME AWAY FROM HOME! Newly renovated 2-bed, one-bath, UPPER LEVEL of home. Located on a quiet street with only minutes to walk to the down town core (restaurants, festival, etc.). Back yard is a wooded area with beautiful gardens and your own deck, bbq and privacy. Out-door furniture and loungers. Open-concept with full kitchen, dining and living room. Bedrooms are very spacious! Don't worry about parking - 2 spaces are just for you! Don't miss out on this place!

Top guest favorite
A modern living area features a gray sectional sofa and a light-colored accent chair. A wooden coffee table sits atop a textured rug. The open kitchen, equipped with stainless steel appliances, is visible in the background, illuminated by natural light from large windows.
Apartment in Elora-Salem
4.96 out of 5 average rating, 109 reviews

Elora's Irvine River Suite

Welcome to your private suite, nestled amongst the trees above Elora’s beautiful Irvine River. Steps to the iconic David Street Bridge offering a birds-eye view of the Gorge, one of the most popular views in the village. Take a 5-10 min scenic walk to the Elora Mill or the many fine restaurants and shops, then come back and enjoy a glass of wine on your private porch. It’s the perfect location for a couples retreat, wedding guests, business traveler, a weekend adventurer or solitude seeker!

Guest favorite
Tiny home in Wellesley
4.99 out of 5 average rating, 132 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?

Guest favorite
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 Saint Marys
4.91 out of 5 average rating, 204 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

Guest favorite
A charming century home is framed by neatly trimmed hedges and vibrant flowering bushes. The inviting front porch with white railings contrasts with the red brick facade, creating an appealing entrance. Lush greenery enhances the peaceful exterior ambiance.
Home in Stratford
4.91 out of 5 average rating, 125 reviews

Garden Oasis - Newly Reno’d Home - Steps to River

Unwind at our two-bedroom century home located steps from the Festival and Tom Patterson theatres. Enjoy morning coffee on the inviting front porch and late night drinks on the patio overlooking the tranquil garden. A fully-equipped kitchen offers the option of preparing a meal to serve in the dining room. The comfortable living room is an ideal spot to catch a movie or watch the news. Upstairs, there's a choice of two bedrooms - a King or a Queen Suite, with a shared four-piece bathroom

Top guest favorite
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, 132 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.

Top guest favorite
Cottage in Stratford
5 out of 5 average rating, 137 reviews

Holiday Getaway | 7mns to Dntwn | Games | Sleeps 8

March Special: Stay 3+ nights and enjoy a complimentary local bakery breakfast basket. Stay 5+ nights and we’ll include the basket plus 4 Stratford Chocolate Trail passes, a self-guided tasting experience at participating downtown shops. Cozy renovated 1200sqft farmhouse just 7 minutes from downtown Stratford, ideal for March Break or group getaways. Sleeps up to 8 with 2 kings, 1 queen, and a pop-up sofa bed. Bright, comfortable space for gathering, games, and relaxed evenings together.

Top guest favorite
A welcoming living area is displayed with a cozy gray sofa and a bright yellow armchair. A wood-burning stove stands beside a wall-mounted television. Natural light enters through a window, illuminating the area rug and a bookshelf filled with books.
Barn in Gads Hill
5 out of 5 average rating, 122 reviews

The Country Nook

This barn style cabin is located 10 -15 minutes from Stratford, Ontario the home of Stratford Festival. This newly renovated 1.5 floor retreat offers an open concept living area, along with two bedrooms with queen size beds. Large windows and a 16 foot ceiling height in the living room add to the brightness of the space. This home away from home offers both comfortable seating inside and a screened in patio nestled into the trees. A way to get away from the city and enjoy the fresh air.

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, 400 reviews

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.

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-Salem
4.97 out of 5 average rating, 874 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, 187 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.

Popular amenities for Shakespeare vacation rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Perth County
  5. Shakespeare