Vacation rentals in Shakespeare

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Top-rated vacation rentals in Shakespeare

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Guest favorite

A lush garden is adorned with vibrant red roses, adding a pop of color. In the background, a seating area with dark chairs is visible, set on well-maintained grass under the dappled shade of surrounding greenery.

Home in Port Dover

4.96 out of 5 average rating, 28 reviews

The Main Street Family Retreat

Welcome to our Port Dover home, a perfect place for families and pet lovers. Just a short walk from the vibrant downtown area and the stunning Port Dover beach, this house offers a unique blend of relaxation and adventure. Our spacious 4-bedroom, 2-bathroom home is designed with comfort in mind, providing a welcoming environment for both kids and pets. Experience the convenience of being close to downtown Port Dover, where you can explore local shops or partake in the town's lively events.

Top guest favorite

An oversized hot tub is situated under a covered area, surrounded by greenery. Soft lighting is present above, enhancing the serene setting. The tub features multiple jets and seating, inviting relaxation in a private outdoor space.

Home in London

4.95 out of 5 average rating, 20 reviews

5BR Luxury Retreat: Hot Tub, Sauna, Pool & More

Welcome to an unparalleled luxury retreat—a 6,800 sq. ft. masterpiece designed for those who appreciate the finest in life. This estate sleeps 16 comfortably, featuring exquisite furnishings, 5 bedrooms, 4 bathrooms, an indoor sauna, oversized hot tub, Olympic pool, heated floors, 2 fireplaces, 2 gourmet kitchens. Located near Boler Mountain, Budweiser Gardens, Storybook Gardens, Museum London 7 min drive to downtown. it’s the ideal destination for an extraordinary luxury getaway in London.

Guest favorite

A spacious wooden porch extends alongside a red cabin, featuring outdoor seating with two chairs and a small table. A BBQ grill is visible in the background, surrounded by a lush green landscape, creating a serene outdoor space for relaxation.

Cabin in Lakeside

4.87 out of 5 average rating, 15 reviews

Cozy Cabin. Think glamping, with a few perks.

Are you looking for a peaceful getaway in the country? Our cozy cabin rental offers a serene setting surrounded by beautiful birch & pine trees, on a scenic country road. This is simple living at its best. Think glamping - but with perks. With Wildwood Conservation Area and Wildwood Lake just 200 meters away, you'll have easy access to many outdoor activities. Explore the biking trails, hike along the Avon trail, go fishing, kayaking, and revel in the natural beauty surrounding you.

Guest favorite

Two wooden chairs are positioned near a fire pit, overlooking the Speed River. Sunlight filters through the trees, casting gentle reflections on the water and creating a serene outdoor space surrounded by nature.

Home in Cambridge

4.92 out of 5 average rating, 379 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!

Superhost

Cabin in Fergus

4.88 out of 5 average rating, 106 reviews

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

Guest favorite

The entryway showcases a neutral-toned wall and a stylish mirror above a decorative table. A vase with flowers adds a touch of elegance. Stairs lead to the upper level, while a spacious hallway offers glimpses of the living areas beyond.

Home in London

4.88 out of 5 average rating, 100 reviews

The Heavenly Sunset

We are thrilled to present Heavenly Sunset; every inch of this property has been lovingly and thoughtfully decorated to present you an experience of upscale casual elegance. A welcoming, open floor plan makes it easy for your group to spend time together AND find quiet moments to yourself. Professional interior design and all-new appliances and furnishings make Heavenly Sunset the perfect setting for your next family vacation, corporate retreat, or romantic couples’ getaway.

Guest favorite

Condo in Elora

4.86 out of 5 average rating, 112 reviews

Elora Grandeur: The Pinnacle Retreat"

Discover a bright and modern 3-bedroom Airbnb in the heart of Elora, perfectly positioned just across from the enchanting Elora Mill. This charming retreat is not only an ideal space for wedding parties to prepare in style and convenience but also a welcoming haven for anyone visiting Elora. With its stylish design and cozy ambiance, it offers a delightful escape where you can relax and unwind. Whether you're drawn to the picturesque views, or the historical charm of Elora.

Guest favorite

A modern kitchen features dark wood cabinets and stainless steel appliances. A spacious island with bar stools invites casual dining, while a subtle backsplash adds texture to the design. Ample natural light enhances the inviting atmosphere.

Home in Lambeth

5 out of 5 average rating, 5 reviews

Luxurious Master Bedroom with Premium Amenities

Welcome to your luxurious haven! This beautifully designed space offers modern amenities, a cozy atmosphere, and a touch of elegance. Perfectly located for both relaxation and exploration, our home features comfortable beds, a fully equipped kitchen, a dining area, a plush sofa, accent chairs, and a full washroom. Whether you’re here for work or leisure, unwind in style and enjoy a stay that feels like a retreat. Book now!

Top guest favorite

The image captures the calm surface of a river reflecting blue skies and surrounding greenery. The view is taken from the bow of a canoe, providing a sense of tranquility with lush trees lining the banks and gentle ripples across the water.

Apartment in Elora

4.96 out of 5 average rating, 278 reviews

Mill View one bedroom apartment . Upper level

Enjoy this stylish one bedroom with pullout couch in the heart of beautiful Elora . Sitting right across from the Elora Mill and Spa . Full kitchen, spa like bathroom and outside porch . Porch overlooking colourful garden and the Mill . Steps to walking trails discovering the Elora gorge . Around the corner are great restaurants and unique shops. Great for a little getaway or attending a wedding at the Elora Mill .

Guest favorite

An aerial view highlights a charming waterfront property with a boathouse and spacious decks along the water's edge. Nearby, multiple homes are visible, surrounded by landscaped areas, showcasing a peaceful residential neighborhood. Ice-covered water indicates a seasonal transition.

Guest suite in Port Dover

4.75 out of 5 average rating, 20 reviews

Spacious 3- bedroom cottage w Pool & Boat dock

Relax with the whole family at this peaceful place to stay. Indoor and out door dining and cooking. Multiple lounging areas inside and out. Heated pool, fire pit, BBQ, paddle boards and kayaks, usage all included. Short walk to downtown dining, shopping and beach. River views to watch the boats go by, sunset views from the multi level patios. Perfect for families or groups of friends to enjoy a space together.

Superhost

An open concept living area is highlighted by vaulted ceilings and exposed beams. A large dining table is flanked by black chairs, while a spacious seating area with a sofa and coffee table is visible in the background. Natural light fills the room through several windows.

Home in Elora

4.77 out of 5 average rating, 264 reviews

Country Oasis in the Village - 4 bed - 2 bath home

Sprawling ranch style home on one of Elora’s most sought after streets. Steps away from Irvine creek and under a 15 minute walk to downtown Elora. The home is set on a massive park-like lot and boasts an expansive open concept living room, dining room and kitchen with cathedral ceilings. The home offers four bedrooms as well as two full bathrooms. Dishwasher, coffee maker and an abundance of parking.

Guest favorite

A serene river view is captured in winter, showcasing a snow-covered landscape along the water. The river is partially frozen, with trees lining the opposite bank. A wooden structure is visible on the riverbank, framed by snow, enhancing the peaceful ambiance.

Loft in Elora

4.97 out of 5 average rating, 381 reviews

Etherington Suites- Riverview Loft with Balcony

This beautiful Riverside loft is newly renovated with an outdoor balcony overlooking the Grand river. Located right downtown Elora, mins away from the Elora Mill and Spa. Our loft is perfect for a romantic, relaxing couples getaway or to get away from the hustle of city life. Mins away from delicious dining, shopping, the famous Elora Gorge, Elora Brewery and Distillery.