Holiday rentals 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
Apartment in Stratford
4.97 out of 5 average rating, 178 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.

Guest favourite
A modern living space features a spacious sectional sofa with decorative pillows. A glass coffee table is positioned on a patterned rug. A kitchenette is visible, equipped with cabinetry, a microwave, and a mini-fridge. Bright overhead lighting enhances the inviting atmosphere.
Guest suite in Stratford
4.82 out of 5 average rating, 396 reviews

The Avon Festival Get-Away

We take pride in ensuring our place is clean, polished and comfortable. A 16 min walk to the Festival Theatre on Queen St. It is a pretty walk along the arboretum and Avon River. We have a well equipped kitchenette, and a high end Kreuig for your tea, coffee, and chai latte needs, all free of charge - also has a cold brew feature! Our basement suite is good for families, couples, solo adventurers, business travellers, and furry friends (pets). The suite has free parking and a private entrance.

Guest favourite
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?

Top guest favourite
The bedroom features a spacious bed with soft blue linens, complemented by two bedside lamps. A comfortable chair is positioned near a window, and a small desk with a lamp is nearby. Natural light filters in through sheer curtains.
Flat in Stratford
4.97 out of 5 average rating, 144 reviews

Boho Chic Suite - walk to dwntwn/free prkg/Netflix

Indulge in our historic yet rejuvenating private apartment suite nestled in one of Stratford's oldest homes. Fully renovated with 1850s charm intact, this main floor retreat offers modern comforts like a full kitchen and a dedicated work desk. The lux queen bed and in-suite laundry allow you to effortlessly extend your stay. Step out onto your private patio for al fresco dining surrounded by lush greenery, or take a short stroll to downtown for a taste of everything the city has to offer!

Guest favourite
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, 240 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
Guest suite in Stratford
4.97 out of 5 average rating, 163 reviews

Private, Self-Contained Unit, Keyless Entry

Located within walking distance of our beautiful waterfront, theatres and downtown core. A guest suite with private entrance, keyless entry, kitchen, bathroom, bedroom, parking, laundry and three shared patios/outdoor spaces to enjoy! Although there is no living room, there is an intimate seating arrangement beside the fireplace to enjoy with a book, coffee or drink. The City of Stratford has implemented a Municipal Accommodation Tax of 4%, which I have had to add to the nightly room fee.

Top guest favourite
Barn in Gads Hill
5 out of 5 average rating, 117 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
Flat in Stratford
4.96 out of 5 average rating, 248 reviews

Debonaire Suites - Arbour: Downtown, Modern, Cozy

Come relax in a modern, calm and comfortable luxury space - lots of natural light from feature windows and skylights, high ceilings, a fireplace (electric) and original brick and natural wood features. The Arbour suite is a 3.7 minute walk to the new Tom Patterson Theatre, and 7 steps to the iconic coffee shop Balzacs. All four theatres, as well as restaurants, shops and parks are an easy walking distance - most guests never use their vehicle once it is parked!

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!

Guest favourite
Loft in Stratford
4.82 out of 5 average rating, 106 reviews

Juno Lofts: Memories of Polonnaruwa

Polonnaruwa Loft: Bohemian Elegance in Heritage Downtown. Perched atop a 1893 heritage property, our loft brings Sri Lankan charm to Stratford. Located in the city centre, enjoy top dining across the street, a 2-min walk to Avon Theatre, and 5 mins to Avon River. Features bohemian design, with access to 3rd floor free laundry. Perfect for those seeking a unique stay near Stratford Festival theatres

Popular amenities for Shakespeare holiday rentals

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