Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

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Guest favorite

Guest suite in Baden

4.9 out of 5 average rating, 168 reviews

Luxury King Suite with Fireplace

Spacious and bright private suite with a full kitchen, king bedroom, living/dinning area with gas fireplace and a full bathroom. Light breakfast foods are available in your kitchen for your use in the mornings. Baden is close to K-W (15 minutes) and just a minute away from the 7/8 expressway. 20 minutes to St. Jacob's market and Stratford. This is an in-law suite on the basement level with extra large windows for a bright and comfortable living space. Great space for business travel or couples.

Guest favorite

Condo in Stratford

4.98 out of 5 average rating, 129 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 favorite

Home in Stratford

4.99 out of 5 average rating, 161 reviews

The Danny - A Unique Stratford Beauty.

The Danny is a beautiful HOME AWAY FROM HOME! Newly renovated 2-bed, one-bath, upper level of home. Located on a quiet street with only minutes to walk to the down town core (restaurants, festival, etc.). Back yard is a wooded area with beautiful gardens and your own deck, bbq and privacy. Out-door furniture and loungers. Open-concept with full kitchen, dining and living room. Bedrooms are very spacious! Don't worry about parking - 2 spaces are just for you! Don't miss out on this place!

Guest favorite

Cottage in Blyth

4.97 out of 5 average rating, 271 reviews

Up The Creek A-Frame Cottage

Relax in an A-frame Cottage over looking a stocked trout pond surrounded by trees. 20 acres of trails. Fish swim, kayak or canoe in the pond or creek. Watch the ducks, frogs, herons, birds, turtles & a variety of wildlife. Enjoy the stars & roast marshmallows at the camp fire. Fully stocked kitchen, BBQ, wood stove, fire pit and 3 piece bathroom. Wood and linens supplied. Ninja course, water mat & trampoline for your use. Groups welcome, extend your group send your request for more info.

Guest favorite

Guest suite in Stratford

4.97 out of 5 average rating, 346 reviews

Beautiful Modern Guestsuite with Private Entry

Located in Stratford on a 2 acre property with mature trees yet steps from many amenities such as grocery stores & restaurants etc. 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. Enjoy the extreme High Speed Fibre Optic internet (551 MBPS). The eat-in kitchen comes well equipped. Unwind on the outdoor patio where you can take in the sunsets or stargaze. Plenty of free parking and no cleaning fees

Guest favorite

Cottage in New Dundee

4.89 out of 5 average rating, 174 reviews

Safe and Clean 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.

Guest favorite

Guest suite in Stratford

4.97 out of 5 average rating, 135 reviews

Private, Self-Contained Unit, Keyless Entry

Located within walking distance of our beautiful waterfront, theatres and downtown core. A guest suite with private entrance, keyless entry, kitchen, bathroom, bedroom, parking, laundry and three shared patios/outdoor spaces to enjoy! Although there is no living room, there is an intimate seating arrangement beside the fireplace to enjoy with a book, coffee or drink. The City of Stratford has implemented a Municipal Accommodation Tax of 4%, which I have had to add to the nightly room fee.

Guest favorite

Cabin in Wallenstein

4.91 out of 5 average rating, 246 reviews

Rustic private getaway 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!

Guest favorite

Home in Elora

4.96 out of 5 average rating, 700 reviews

Elora Heritage House

Welcome to Elora Heritage House, where unforgettable experiences await in the heart of Elora. Built in the 19th century, our meticulously crafted home exemplifies quality and attention to detail. Discover carefully curated rooms with mid-century furniture, modern design, and a nostalgic ambiance. Nestled amidst serene trees, generous natural surroundings, world-class dining, and shops are just steps away. Embrace the essence of Elora at our cozy haven.

Guest favorite

Guest suite in Stratford

4.97 out of 5 average rating, 196 reviews

Private airy space in a perfect location

With a walkable score of 86, our private room in a friendly neighbourhood is ideal for your visit to Stratford. This space has hard wood floors, high ceilings, ceiling fan and heating/central air conditioning. A cozy electric fireplace to relax in winter. Our central location is just minutes away from all 3 theaters, as well as the Avon River, various parks, the tennis club, and all that downtown has to offer. A private parking space is included.

Guest favorite

Guest suite in Newton

4.91 out of 5 average rating, 243 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, reliable wifi, outdoor hot tub, pool and a patio with firepit. The famous Anna Mae's Restaurant and the Zehr's Country Market are 1 km down the road.

Guest favorite

Cottage in St. Jacobs

4.99 out of 5 average rating, 143 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.