Holiday rentals 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 spacious bed with neutral bedding is flanked by two bedside tables, each adorned with a lamp. Pillows are neatly arranged, providing comfort. An alarm clock is placed on one side, and soft lighting creates a calming ambiance.
Flat in Beechwood
4.95 out of 5 average rating, 118 reviews

The wRen's Nest

The "wRen's Nest" is a peaceful and relaxing space, ideal for a comfortable night's sleep. Located 2 km from the UWaterloo, or 3 km from WLU, with several walking trails, gyms, and plenty of fantastic eating options to choose from. There is free parking and a private entrance to the one bedroom, one bathroom basement apartment, featuring a full kitchen if you love cooking! A spacious back yard offers a shared (with hosts) patio to enjoy the birds singing and a cup of coffee to start your day.

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
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, 390 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.

Top guest favourite
A stone pathway leads to the exterior of a small wooden cabin, surrounded by lush greenery. Hanging flower baskets adorn the walls, and a tranquil water feature can be seen nearby. The natural scenery creates a peaceful atmosphere, inviting exploration.
Tiny home in The Junction
4.99 out of 5 average rating, 187 reviews

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

Guest favourite
Tiny home in Wellesley
4.99 out of 5 average rating, 130 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
4.96 out of 5 average rating, 142 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!

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, 112 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 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.
Apartment in Stratford
4.96 out of 5 average rating, 215 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)

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, 124 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.

Guest favourite
A comfortable living area features a light sofa adorned with soft cushions, positioned near a large window framed by exposed brick walls. A unique coffee table sits in front, while stylish floor lamps provide ambient lighting. A wooden side table completes the inviting space.
Apartment in Stratford
4.83 out of 5 average rating, 236 reviews

Bradshaw Lofts: The Baldwyn

Discover a piece of Stratford's industrial past at the newly restored Bradshaw Lofts. Heritage meets modernity in this luxury 2 bedroom suite. This historic gem in the heart of Stratford features classical Edwardian industrial architecture with tasteful, modern elegance. Convenience abounds with ensuite laundry and a fully equipped kitchen. It's just a short walk from the loft to discover all that Stratford has to offer from restaurants and shopping to waterfront walking trails.

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, 284 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
A modern living area features exposed brick walls and natural light from large windows. A cozy sofa is complemented by a round coffee table on a decorative area rug, while stylish bar stools are positioned at an open kitchen counter adorned with indoor plants.
Flat in Stratford
4.91 out of 5 average rating, 121 reviews

Bradshaw Lofts: The Marrakesh

Marrakesh Loft: Exotic Charm in Stratford's Bradshaw Lofts. Discover the Marrakesh, a stunning 2 bedroom loft that marries the historical allure of 1902 architecture with the vibrant essence of Old World Maghrib. Enjoy exposed brick, modern finishings, and original art. Fully equipped with a kitchen and laundry ensuite, it’s nestled in the heart of downtown, steps from the Stratford Festival theatres, shops, and Lake Victoria

Popular amenities for Shakespeare holiday rentals

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