Vacation rentals in Shakespeare

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.

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

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?

Boho 4-Bed House Retreat: HotTub, Sauna Oasis &Spa

Experience luxury in this tranquil full house in Saint Jacobs village, set on a fully fenced acre lot for privacy. It features three bedrooms: 1 king, 1queen, 2 single beds, Double Bed with office. The house includes two living rooms, two full bathrooms, and a well-equipped kitchen. Highlight is the retreat oasis with a hot tub, sauna, and outdoor shower. Enjoy spa-like bathrooms with rain showers and a private outdoor patio. Nearby dining and entertainment enhance your rejuvenating getaway!

Holiday Getaway | 7mns to Dntwn | Games | Sleeps 8

Beautifully renovated 1200 sq ft farmhouse just 7 minutes from downtown Stratford — perfect for theatre trips, family getaways, and weekends with friends. Sleeps up to 8 guests with 2 king beds, 1 queen, and a pop-up sofa bed. Enjoy bright gathering spaces, games, patio dining, and cozy evenings after exploring Stratford’s theatres, cafés, shops, and restaurants. For select stays, guests may enjoy a complimentary local welcome treat featuring bakery items, wine, or other local favourites.

Melville Guesthouse

Welcome to The Melville Guesthouse, a charming one-bedroom retreat on a quiet street in Elora. Enjoy the privacy of your yard while being a short walk from downtown, the Elora Centre for the Arts, the river, and historic homes. Whether you’re here for trails, boutique shops, or Elora’s arts and dining scene, our standalone guesthouse offers comfort and convenience—perfect for couples and families, with a pull-out couch for extra guests. Ideally located, you’re near everything Elora offers.

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.

GG’s Place | Character | Steps to Downtown

A charming queen bedroom apartment flooded with natural light and a simple yet chic design to accent the character and historic elements of the space. Fully equipped kitchen and a spacious living area, the apartment is a short walk to downtown restaurants, patios, coffee & independent shops. Wander a few minutes further and you will find yourself at Stratford's picturesque Lake Victoria park. Be sure to check out Pretty Pretty Boutique Suites as well! www.airbnb.ca/h/prettypretty

"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!

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!

Bradshaw Lofts: The Penthouse

Experience luxury in Stratford’s historic Bradshaw Lofts. This penthouse suite offers two king bedrooms, two full bathrooms (one ensuite), in-suite laundry, and a skylight that bathes the space in natural light. Steps to the Avon Theatre, Stratford Festival stages, and top dining, cafés, and boutiques. A perfect heritage suite for couples, families, or friends seeking comfort, culture, and style in Ontario’s premier Shakespearean arts destination.

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.