Holiday houses in Shakespeare

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Top-rated holiday rentals in Shakespeare

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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.

Guest favourite
The living area features a sleek black entertainment center with a large television and decorative glass display cabinets. A coffee table is positioned in front of a dark leather sofa, with warm wood flooring and exposed brick walls adding character to the space.
Condo in Stratford
4.97 out of 5 average rating, 180 reviews

The Loft on Downie - Downtown Stratford

Located on the top floor, with a view of downtown, our 450 square foot condo is steps away from the heart of downtown Stratford and all it has to offer including cozy coffee shops, elegant restaurants, the Avon Theatre, close to the famous Stratford festival, and other shops for all to enjoy. Perfect for a couple’s getaway or to enjoy as friends travelling together. Our condo offers all the essentials including a luxurious queen bed, fully equipped kitchen, a 55” smart TV and ensuite laundry.

Top Guest favourite
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, 242 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

Guest favourite
A small cabin with a red roof is set amidst a green lawn, surrounded by trees. A campfire pit, with smoke rising gently, is situated in front of the cabin. A rustic wooden table is nearby, enhancing the natural outdoor setting.
Tiny home in Wellesley
4.99 out of 5 average rating, 136 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 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, 129 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
The exterior of a modern, dark-toned tiny home is framed by trees. A private dock with Adirondack chairs sits by the water, reflecting the structure's warm lights. The tranquil setting is enhanced by the surrounding natural landscape and evening ambiance.
Shipping container in Puslinch
4.99 out of 5 average rating, 105 reviews

Wildwood Tiny Home Escape with Wood Fired Sauna

Welcome to an absolutely unique converted shipping container – Wildwood Tiny Home! This converted shipping container has a big personality! If you and your guests are looking for luxury, nature, peace, serenity, and a chance to escape the city – this getaway is perfect for you! At Wildwood Tiny Home, you can fill your time with hanging out on your own private beach & waterfront dock, enjoying your firepit, beach volleyball, horseshoes, cornhole, badminton, board games, and many more!

Top Guest favourite
An elegantly designed building features a unique glass extension reflecting the surrounding nature. Multiple levels are connected by balconies with black railings, while wooden accents add warmth. A large umbrella is visible on the upper deck, creating a welcoming outdoor space.
Guest suite in Elora
5 out of 5 average rating, 457 reviews

Karger Gallery Suite

Located within Elora's downtown core, the Karger Suite is only a few short steps to the many fine restaurants and the Elora Mill. Enjoy the views and vibes of being in the heart of Ontario's most beautiful village. The private suite overlooks pine trees, century-old stone walls, angled rooftops and the charming village of Elora. Enjoy a glass of wine on your private 1500 sq. ft. third floor patio, keeping warm and cozy beside the fire-table. Day or night the views are enchanting.

Top Guest favourite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 380 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 indoor 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 favourite
Cottage in Stratford
5 out of 5 average rating, 141 reviews

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

March Special: Stay 2+ nights and enjoy a complimentary local bakery breakfast basket. Stay 3+ nights and we’ll include 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 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
4.97 out of 5 average rating, 317 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
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, 192 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 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.
Apartment in Stratford
4.98 out of 5 average rating, 239 reviews

GG’s Place | Character | Steps to Downtown

A charming 1 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 with kitchen amenities, a queen size bed, and a spacious kitchen and living area, the apartment is a short walk to downtown restaurants, patios, coffee & independent merchants. Wander a few minutes further and you will find yourself at Stratford's picturesque Lake Victoria park.

Popular amenities for Shakespeare holiday rentals

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