Vacation rentals in Shakespeare

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shakespeare

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
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, 109 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.

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 homes in Wellesley
4.99 out of 5 average rating, 137 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 highlighted by a brown leather sofa and a glass coffee table with a wooden base. A cozy fireplace is flanked by ornamental decorations, while soft drapes frame a window. The floor is covered with plush, light-colored carpeting.
Apartment in Linwood
5 out of 5 average rating, 137 reviews

The Olde Chick Hatchery

Our spacious, newly updated, 3-bedroom apartment is nestled within the heart of Waterloo Region's Mennonite and Amish Community. This unique Airbnb, a former chick hatchery, is flooded with natural light, creating a warm and inviting atmosphere. Our huge rooftop patio provides a perfect spot for relaxing. Prepare delicious meals in our fully equipped kitchen. Conveniently located 10 minutes from the village of St. Jacobs, 15 minutes from Waterloo and along the Guelph to Goderich trail.

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, 131 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
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, 458 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
A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.
Home in Cambridge
4.93 out of 5 average rating, 452 reviews

"Cottage Home On The River" 1 Bedroom

Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

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 homes in Arthur
4.97 out of 5 average rating, 381 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.

Guest favourite
A charming exterior of Henry House is presented under a clear evening sky. The entrance features a welcoming pathway leading to a stately door with red accents, flanked by well-maintained greenery and softly lit windows capturing the inviting atmosphere inside.
Apartment in Stratford
4.94 out of 5 average rating, 108 reviews

Lake Suite with Sunroom by Henry House Stays

Henry House Lake Suite -- an ode to the rich architectural heritage of Stratford. We are branded online as "Henry House Stays Stratford" and are sought after as a place to celebrate birthdays and anniversaries. The exquisite bed sets the tone of this stately-yet-comfortable space for a night of sweet dreams that you may actually remember when you awake. The Sun Room is the perfect, tranquil spot to enjoy your morning coffee while you watch the river and sidewalks come alive.

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 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, 193 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.

Guest favourite
A scenic view of the property is presented, featuring a charming lamp post in the foreground and a well-maintained pathway leading to the house. The exterior showcases a blend of traditional and modern architecture, surrounded by lush greenery and a carefully landscaped yard.
Guest suite in Newton
4.92 out of 5 average rating, 322 reviews

Century Home Apartment next to the G2G Trail

This rural property is a great place to relax and unwind in the heart of Amish and Mennonite country. The location is perfect for outdoor enthusiasts with the G2G hiking/biking trail literally being in the backyard. The second storey Apartment has lots of charm and character. There is ample parking and reliable wifi. The famous Anna Mae's Restaurant and the Zehr's Country Market are 1 km down the road.

Popular amenities for Shakespeare vacation rentals

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