Vacation rentals in Shakespeare

Cozy Stay! | Stratford within 10 minutes

A charming, fully equipped private guest suite apartment tucked at the back of large vintage home, which includes a serene spa at the front in the quaint village of Shakespeare, just 10 minutes from Stratford! This cozy vintage retreat features a 1-acre backyard with stunning farmland views and breathtaking sunsets under maple trees. Host Sherry has lovingly transformed this space into a peaceful haven, perfect for relaxing getaways. Enhance your stay with spa treatments for the ultimate escape!

The Artist's Loft

Welcome to The Artist’s Loft! This unique stay at the historic Bradshaw Lofts downtown Stratford features a fully functional kitchen, ensuite laundry, large bathroom, a cozy bedroom, and a living space for relaxing, dining or working. All of this is contained by the historic elements the building has - natural timber, exposed brick walls and high ceilings. Run by a local artist and counsellor, we are committed to sharing the beautiful town that we have fallen in love with, with a personal touch.

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.

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.

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.

Cozy country getaway -clawfoot tub & starry nights

Escape to our peaceful 2-bedroom country guest house, nestled among beautiful farmland with stunning views. A tranquil retreat or a base to explore the nearby Stratford area, this modern farmhouse-style suite is the perfect getaway for up to 5 guests. Relax in a cozy yet spacious setting featuring two queen beds, an electric fireplace, and a walk-in shower with a luxurious soaker tub. Enjoy the quiet of the countryside with an outdoor fire pit and BBQ. Washer and dryer and Wi-Fi are included.

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!

The Downtown Flat on Margaret

Welcome to The Downtown Flat on Margaret! This cozy 1-bed, 1-bath apartment is small but mighty. Situated in the heart of downtown, you’ll be just a walk away from everything you need. Centrally located to the VIA Rail train station, LRT, the Aud, Centre in the Square, and the many shops and restaurants of Kitchener. Fully equipped kitchen, modern design, smart TV, in-suite laundry, a workspace, and air conditioning. A perfect home away from home for both short and long term stays.

The Mill Loft at Punkeydoodles

The Mill Loft at Punkeydoodles is a 1100 sq ft oasis tucked in a quaint rural setting near New Hamburg ON. This 2 bedroom guest apartment is centrally located between Stratford, St. Jacobs and the K-W Region. Located above a detached garage, the Mill Loft offers a peaceful, private setting with full kitchen, two bedrooms, three piece bath and laundry. Large windows offer a stunning sunrise view and the outdoor deck provides a tranquil spot for a morning coffee or afternoon retreat.

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.

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.

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!