Vacation rentals in Shakespeare

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shakespeare

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A cozy seating area is set along one side of the bus, featuring a built-in wooden bench adorned with patterned cushions and decorative pillows. Natural light fills the space through multiple windows, creating a bright and inviting atmosphere. A woven rug enhances the earthy feel.

Camper/RV in Mitchell

4.86 out of 5 average rating, 58 reviews

Free to Wander 2.0

Converted school bus, designed as an escape for those seeking a break from the ordinary, those who love to wander, or even those who need a quiet vacation. Nestled in the woods along the Upper Thames River, wildlife can often be spotted while enjoying the sunrise or sunset. With windows all around, it’s a fully immersive experience. Note: Heated ( Propane Heat) & Insulated. Water included. Electricity available in limited amounts. No shower RV style toilet inside bus Currently no TV or WiFi

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

4.91 out of 5 average rating, 23 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

4.88 out of 5 average rating, 16 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, 385 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

An outdoor dining area features a spacious black table surrounded by eight chairs, situated on a wooden deck. An adjacent outdoor kitchen displays multiple stainless steel grills. Lush greenery and the cottage are visible in the background under a bright blue sky.

Cabin in Fergus

4.88 out of 5 average rating, 109 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.

Top guest favorite

An inviting outdoor area features a lit-covered deck with a hot tub, surrounded by wooden beams and string lights, creating a cozy ambiance at night. A staircase leads up to the deck, while large glass doors provide access to the interior.

Guest suite in Elora

4.97 out of 5 average rating, 59 reviews

The Carlton Elora | Cozy Retreat with Hot Tub

Discover The Carlton, Elora. A stylish retreat just steps away from the village’s charming shops and delightful restaurants. This centrally located lower-level apartment is completely private and perfect for couples, small families, or solo travelers. Explore the scenic beauty of the Elora Gorge and local art, then return to relax in your hot tub under the stars. Experience the best of Elora in a space designed for relaxation and enjoyment. Excited to host you soon!

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

A inviting pool area is illuminated by soft lighting, surrounded by comfortable seating options. Natural stone and wood elements create a harmonious connection with the landscaped garden. The serene water reflects the night sky, enhancing the tranquil ambiance of the outdoor space.

Guesthouse in Delhi

4.97 out of 5 average rating, 135 reviews

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

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, 284 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 .

Superhost

The exterior of the ranch-style home is surrounded by lush greenery, featuring tall trees and expansive grass. A welcoming entrance with a red door is visible, framed by well-maintained landscaping, creating a serene and inviting setting.

Home in Elora

4.77 out of 5 average rating, 265 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, 383 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.