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Holiday houses in Shakespeare

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Top-rated holiday rentals in Shakespeare

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 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 favourite
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, 107 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 favourite
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 favourite
A cozy seating area features a light gray sectional sofa adorned with decorative pillows. The deep blue wall is complemented by two framed artworks, enhancing the space's style. A small round basket rests on the floor, contributing to the casual ambiance.
Cottage in Stratford
5 out of 5 average rating, 137 reviews

Farmhouse | 7 mins to Dwntwn | Games | Sleeps 7

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
4.86 out of 5 average rating, 243 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.

Top Guest favourite
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 favourite
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, 121 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 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
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 favourite
A serene view of Alder Lake is captured, featuring a wooden dock with red Adirondack chairs. Lush greenery frames the scene, including a large, weeping willow tree. Kayaks are visible along the shoreline, with calm waters reflecting the bright blue sky and scattered clouds.
Cottage in New Dundee
4.89 out of 5 average rating, 130 reviews

Cosy Lakefront Cottage

Enjoy 150 feet of lakefront just outside the city limits. This fully remodeled cottage has fun for all to enjoy. There are kayaks, a canoe and a paddle boat for those that live on the water. We also have floaties if you just want to lounge and relax by the water. In the winter months you can also bring your ice skates and enjoy skating on the lake and then coming inside for a hot drink by the propane fireplace. The 800 square feet of deck overlooks the water for all your needs.

Top Guest favourite
A stylish open-concept living area features a comfortable sofa with accent pillows and a sleek coffee table. A dining space with a round table is visible, and modern lighting fixtures hang from the ceiling. A staircase leads to the upper level, and a potted plant adds a touch of greenery.
Apartment in Elora-Salem
4.97 out of 5 average rating, 304 reviews

The Evelyn Suites - Suite A - Luxury Pied-à-Terre

Hello! We are MacLean & Sarah, owners of The Evelyn Restaurant and The Evelyn Suites. Centrally located in a historic, limestone building on a Main Street in Elora, this beautifully appointed, French modern style, 2 bedroom apartment is within walking distance of everything the village has to offer, including the Elora Gorge, Shops, Restaurants and The Elora Mill & Spa. We look forward to hosting you while you relax and enjoy your stay in our luxurious pied-à-terre!

Top Guest favourite
The exterior of the cabin features warm wooden logs and a welcoming entrance framed by vibrant flower beds. A stone pathway leads to the door, bordered by landscape lighting. A tall blue spruce tree and rustic wheel complement the natural surroundings.
Cabin in Wallenstein
4.92 out of 5 average rating, 286 reviews

Cozy Cabin with Jacuzzi tub

Walnut Hill Cabin is a beautiful cabin located near the historic village of St. Jacobs. We invite you to come relax in our oasis, we love our place and are happy to share our cabin with you! Kitchenette and continental breakfast is included. Great for business travel. Come, relax and refresh while watching squirrels and birds play A great couples weekend getaway! We thoroughly clean after every visit. When you book you get the whole cabin to yourself!

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, 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 holiday rentals

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