
Holiday houses in Shakespeare
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Top-rated holiday rentals in Shakespeare
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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.

Elora's Irvine River Suite
Welcome to your private suite, nestled amongst the trees above Elora’s beautiful Irvine River. Steps to the iconic David Street Bridge offering a birds-eye view of the Gorge, one of the most popular views in the village. Take a 5-10 min scenic walk to the Elora Mill or the many fine restaurants and shops, then come back and enjoy a glass of wine on your private porch. It’s the perfect location for a couples retreat, wedding guests, business traveler, a weekend adventurer or solitude seeker!

Garden Oasis - Newly Reno’d Home - Steps to River
Unwind at our two-bedroom century home located steps from the Festival and Tom Patterson theatres. Enjoy morning coffee on the inviting front porch and late night drinks on the patio overlooking the tranquil garden. A fully-equipped kitchen offers the option of preparing a meal to serve in the dining room. The comfortable living room is an ideal spot to catch a movie or watch the news. Upstairs, there's a choice of two bedrooms - a King or a Queen Suite, with a shared four-piece bathroom

Farmhouse | 7 mins to Dwntwn | Games | Sleeps 7
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!

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.

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.

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.

Spacious Suite • Short drive to Downtown/Festivals
Minutes from the Stratford Festival and direct down Huron St. to the downtown core, this private two-level guest suite offers a quiet, comfortable retreat with easy access to theatres, restaurants, grocery stores and shops. Ideal for festival-goers, weekend getaways, and longer stays. Enjoy self check-in with private keyless entry and convenient free parking. Guests love the High Speed Fibre Optic internet (551 MBPS), the well equipped eat-in kitchen, and the quiet backyard patio.

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.

The Evelyn Suites - Suite A - Luxury Pied-à-Terre
Hello! We are MacLean & Sarah, owners of The Evelyn Restaurant and The Evelyn Suites. Centrally located in a historic, limestone building on a Main Street in Elora, this beautifully appointed, French modern style, 2 bedroom apartment is within walking distance of everything the village has to offer, including the Elora Gorge, Shops, Restaurants and The Elora Mill & Spa. We look forward to hosting you while you relax and enjoy your stay in our luxurious pied-à-terre!

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!

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.
Popular amenities for Shakespeare holiday rentals
Other great holiday rentals in Shakespeare

The Millertime Experience

Private, spacious bungalow with hot tub

The Kabin

Fern Hill Cabin

Stylish Downtown Suite with Patio & City Views

Gateway Inn: Cora's Loft

Cozy Private Suite with Year-Round Hot Tub

The Mornington Bloom
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- Grand Bend Beach
- Wilfrid Laurier University
- Glen Eden
- Victoria Park
- Boler Mountain
- Royal Botanical Gardens
- University of Waterloo
- Bayfront Park
- FirstOntario Centre
- Budweiser Gardens
- Dundurn Castle
- Western University
- Elora Gorge
- Art Gallery of Hamilton
- University of Guelph
- Conestoga College
- Conestoga College
- Elora Quarry Conservation Area
- Springbank Park
- Cambridge Butterfly Conservatory
- McMaster University
- Dundas Peak
- Waterloo Park
- Grand Theatre




