Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

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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.
Apartment in Beechwood
4.95 out of 5 average rating, 121 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
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, 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.

Top guest favourite
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
4.98 out of 5 average rating, 264 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!

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, 391 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 homes in The Junction
4.99 out of 5 average rating, 193 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 homes 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.
Apartment 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!

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, 238 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 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, 115 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 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, 125 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
Apartment in Stratford
4.96 out of 5 average rating, 246 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!

Popular amenities for Shakespeare vacation rentals

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