Holiday houses in Shakespeare

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Top-rated holiday 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, 112 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.

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, 395 reviews

Your ‘Home on Huron’ | 2 levels | Private Entry

Located on the edge of Stratford on a 2 acre property with plenty of mature trees, yet steps from many amenities such as grocery, coffee, & ice cream shops & restaurants. Enjoy self check-in with your own private keyless entry, 2 floors of open-concept living, lots of windows & skylights to let natural light in. Guests love the High Speed Fibre Optic internet (551 MBPS). The eat-in kitchen comes well equipped. Unwind on the outdoor patio. There is plenty of free parking and no cleaning fees.

Guest favourite
Tiny home in Wellesley
4.99 out of 5 average rating, 129 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 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, 130 reviews

7 mins to Dtwn Theatres, Holiday Getaway - 2KG/1QN

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!

Top Guest favourite
A comfortable sleeping area features a spacious bed dressed in a patterned white and gray quilt. A microwave is placed nearby, along with a decorative screen partition. The bathroom area is visible in the background, showcasing essential amenities.
Apartment in Thamesford
4.96 out of 5 average rating, 293 reviews

Stay Inn Thamesford - Cozy 1 Bedroom unit/apt.

Enjoy a relaxing stay in our stylish and cozy little nook right in the hub of our friendly little town. Walking distance to Tim Horton's, RBC bank, variety stores, pizza pick up, town swimming pool, cannabis store and liquor & beer . Only 20 minutes London or Woodstock . It's important to note that our quaint unit does have a saniflo toilet and pumping system(ie. maceration system) which means there is noise associated with flushing and drainage. Please inquire if more info is needed!!

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, 109 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 tiny home is presented, featuring large glass panels that allow natural light to fill the interior. An open door reveals a glimpse of the modern decor inside. Surrounding greenery adds to the serene atmosphere of the property.
Tiny home in Arthur
4.97 out of 5 average rating, 341 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
A cozy studio space features high ceilings with exposed wooden beams and a bright, airy atmosphere. A double bed is adorned with a soft blanket, while a seating area with a rattan chair and small sofa invites relaxation. Natural light flows through large windows, illuminating the room.
Guesthouse in The Junction
4.91 out of 5 average rating, 586 reviews

Sweet Studio Cottage Cozy Fireplace Backyard Haven

Experience a private, urban studio cottage located in a gorgeous tree-filled backyard in the Junction neighbourhood, close to downtown Guelph, with full amenities. Comfortable queen bed, natural gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, additional sleeping loft, private back flagstone patio, and sauna. Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

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, 283 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 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.
Apartment in Stratford
4.91 out of 5 average rating, 117 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

Top Guest favourite
A spacious master bedroom features a large bed with white linens and decorative pillows. Exposed brick walls enhance the rustic charm, complemented by wooden beams overhead. A cozy bench covered in a soft throw sits at the foot of the bed, with framed art arranged above.
Apartment in Stratford
4.96 out of 5 average rating, 431 reviews

Wow, Two Chic King suites- Walk to DT/Theatre's

Experience all that Stratford has to offer from this updated 2-bed, 2-bath vacation rental home. As former servants quarters, this unique home was the first house built on the north side of the river in Stratford. With sleeping for 6 and a furnished outdoor space, plus a prime location within walking distance of town's theatres, there's no better place to spend your Ontario getaway then this charming abode!

Popular amenities for Shakespeare holiday rentals

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