Vacation rentals in Wellesley

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Top-rated vacation rentals in Wellesley

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Top guest favorite
A comfortable sleeping area features a spacious bed adorned with soft pillows and a textured throw. Two inviting armchairs are positioned nearby, complemented by a bedside lamp that offers ambient lighting. A decorative tree and framed artwork add a touch of warmth to the space.
Apartment in Beechwood
4.95 out of 5 average rating, 127 reviews

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.

Top guest favorite
A vintage schoolhouse stands in the background, showcasing its distinctive architecture and large windows. In the foreground, a well-crafted bike rack holds several bicycles under a shaded canopy, surrounded by autumn foliage and a gravel pathway.
Home in New Hamburg
5 out of 5 average rating, 108 reviews

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.

Guest favorite
A modern living space features a spacious sectional sofa with decorative pillows. A glass coffee table is positioned on a patterned rug. A kitchenette is visible, equipped with cabinetry, a microwave, and a mini-fridge. Bright overhead lighting enhances the inviting atmosphere.
Guest suite in Stratford
4.82 out of 5 average rating, 398 reviews

The Avon Festival Get-Away

We take pride in ensuring our place is clean, polished and comfortable. A 16 min walk to the Festival Theatre on Queen St. It is a pretty walk along the arboretum and Avon River. We have a well equipped kitchenette, and a high end Kreuig for your tea, coffee, and chai latte needs, all free of charge - also has a cold brew feature! Our basement suite is good for families, couples, solo adventurers, business travellers, and furry friends (pets). The suite has free parking and a private entrance.

Superhost
A bright bedroom features a spacious bed with neutral bedding, complemented by a textured throw. A large window allows natural light to fill the room. A wall-mounted TV is positioned opposite a dedicated workspace with a sleek chair, creating a functional and inviting atmosphere.
Apartment in Kitchener
4.86 out of 5 average rating, 130 reviews

Entire Bachelor Apartment With Free Parking

This apartment has everything you need for your KW stay! Located steps from the Grand River and Joe Thompson park, there is an abundance of nature to explore while you’re in town. A central point between Kitchener and Waterloo, it’s less than a minute away from Highway 85 and a 5 minute drive to either Uptown Waterloo or downtown kitchener. Grand river hospital, University of Waterloo and Laurier University are all also less than a 10 minute drive. An ideal base to explore what KW has to offer!

Top guest favorite
A stone pathway leads to the exterior of a small wooden cabin, surrounded by lush greenery. Hanging flower baskets adorn the walls, and a tranquil water feature can be seen nearby. The natural scenery creates a peaceful atmosphere, inviting exploration.
Tiny home in The Junction
4.99 out of 5 average rating, 195 reviews

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

Guest favorite
Tiny home in Wellesley
4.99 out of 5 average rating, 132 reviews

RUSTlC~OFFGRlD~OASlS&MlCRO-CABlN

Are you looking for a space to get away, a peaceful oasis immersed in nature? Welcome to Clemmer's Chaos Rustic Escape! It's off-grid. No electricity. No running water. No Wi-Fi. There are bugs and critters. An outhouse for your business. A Cabin for two. A Space for Tents. A mini lake. You can swim, fish, canoe. There is a campfire pit, to cook over, sing around, or listen to the soft sounds of nature and crackling fire as you stare up at the stars. This is an experience. Au Naturel. You in?

Guest favorite
A serene outdoor seating area features two light-colored chairs facing a small red table. Beyond lies a calm lake surrounded by trees, with a hanging ornament visible above. The ground is covered in grass, offering a peaceful spot to relax.
Cottage in New Dundee
4.86 out of 5 average rating, 240 reviews

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.

Top guest favorite
Apartment in Linwood
5 out of 5 average rating, 132 reviews

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.

Top guest favorite
Barn in Gads Hill
5 out of 5 average rating, 119 reviews

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.

Top guest favorite
Tiny home in Arthur
4.97 out of 5 average rating, 363 reviews

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.

Top guest favorite
The modern kitchen is equipped with stainless steel appliances, including a large refrigerator and oven. Light wood cabinetry complements the spacious countertops. A dining table with four chairs is positioned nearby, while a decorative plant adds a touch of greenery to the inviting atmosphere.
Guest suite in Cedar Hill
4.92 out of 5 average rating, 248 reviews

Outdoor Hot Tub Bliss: 2Bed/2Bath Garden Suite DTK

Welcome to our luxurious garden suite with a private outdoor hot tub, perfect for relaxation! Located in downtown Kitchener, it’s steps from cafes, bakeries, restaurants, and the weekend farmers market. This 2Bed/2Bath suite includes a fully equipped kitchen, washer/dryer, and stunning new flooring. With quick access to highways, transit lines to colleges and universities, and the Iron Horse Trail, it’s the ideal space for families, workers, and students. Parking is also included!

Superhost
A modern living area features a comfortable gray sofa adorned with pink and patterned pillows. A wooden side table with a candle sits nearby, while a workspace with a desk and chair is positioned against the wall. Natural light enters through the window, accompanied by warm orange curtains.
Guest suite in Kitchener
4.88 out of 5 average rating, 114 reviews

Modern apartment 5 mins to GO, Goog|e, downtown

A cozy stay at the downstairs unit of a century home. The space is full of character & has been recently updated with many stylish and modern features. Enjoy convenience and comfort, whether you are travelling for work or pleasure. Situated on the outskirts of downtown Kitchener, we are a 5 minute walk to the GO train station, bars & restaurants, Goo/gle offices and LRT. The neighbourhood is mature & quiet, home to many wonderful families who have lived here for decades.

Popular amenities for Wellesley vacation rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Region of Waterloo
  5. Wellesley