Guesthouse vacation rentals in Essex County

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Top-rated guesthouse rentals in Essex County

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Top guest favorite
A lake house is situated on the shoreline of Lake Erie, featuring a sloped path with steps leading down to it. Soft lights illuminate the exterior during twilight, creating a warm ambiance. The tranquil water extends to the horizon, inviting a peaceful retreat.
Guesthouse in Kingsville
4.98 out of 5 average rating, 731 reviews

Small lake house on Lake Erie shore

Private Bachelor apartment sized house directly on Lake Erie. ULTRA FAST WI-FI, Private deck, Kayaks. The Cottage is always toasty warm all winter long. Queen bed, bathroom with shower, kitchenette. Great swimming in shallow, sandy waters. Cottage is only a few minutes from many area wineries, breweries, distilleries and fantastic restaurants serving local food. Walking distance to Pelee Island ferry. Want something completely different? This is the place. It's almost like staying on a boat.

Guesthouse in Windsor
New place to stay

Quiet, cozy private Suite w/ Separate Entrance

Quiet, private main-floor suite with separate entrance. This is a fully self-contained living space with its own private entry, while the owners occupy the front portion of the home. For this reason, only registered guests allowed on premise at all times. Access to a shared backyard. Best suited for respectful, low-noise guests looking for a peaceful and comfortable home base. Conveniently located near the new upcoming Gordie Howe Bridge, with quick access to Highway 401 and other major routes.

Top guest favorite
A serene view of the lake is framed by lush greenery. Soft pastel colors in the sky reflect the sunset over calm waters, creating a tranquil setting for relaxation. A wooden staircase leads down to the inviting water's edge, surrounded by natural foliage.
Guesthouse in Essex
4.99 out of 5 average rating, 108 reviews

Premiere Cottage-Heart of Wine County/ Lake Access

Our stunning guest house sits high on the Oxley bluff, nestled in the middle of wine county. This spectacular space is truly the premiere of what Oxley has to offer. Shared access to massive over-size deck for large gatherings provides pristine lake views. Staircase leads to secluded deck with private beach. This modern & stylish property features 1 bedroom, 1 bathroom and a wood burning stove fireplace, making it a comfortable stay for any time of year. You simply won't find better in Oxley!

Top guest favorite
A spacious backyard stretches toward the waterfront, featuring a sandy beach bordered by a rocky shore. Two white chairs are positioned on the lawn, under the shade of lush trees. A wooden pathway leads to the water, enhancing the tranquil outdoor setting.
Guesthouse in Amherstburg
5 out of 5 average rating, 16 reviews

Lake Erie Retreat:Waterfront Apt

Stunning Views from Sunrise to Sunset. Unwind in peaceful relaxation with breathtaking views that stir the soul from the first morning light to glowing Lake Erie sunsets. Nestled just less than 10min from the historic town of Amherstburg, our cozy apartment fully equipped, offers the perfect blend of comfort, nature, and convenience with a private beach, and an expansive backyard. Step out onto your private deck to enjoy breakfast while watching swans glide by and birds singing in the trees.

An exterior view of the upper unit cottage is presented, featuring a set of wooden stairs leading to the private entrance. A decorative lamp post stands near the charming wooden fence, while a green lawn and landscaped shrubs enhance the setting.
Guesthouse in Leamington
4.39 out of 5 average rating, 31 reviews

Belle Loft | Private Waterfront

Enjoy a private waterfront experience on the shores of Lake Erie. The Loft is the upper unit cottage on a private 3 acre property. A 700 square foot deck is yours to relax and lounge on. With an amazing view of the Lake. All the amenities you need for the perfect Essex County experience are waiting for you. Enjoy Lake access on the eastern part of the property. Seacliff Park and Point Pelee are a brief drive away. The cottage has been modernized and decorated to host you and yours.

Guest favorite
A wooden deck features a glass-topped table surrounded by colorful Adirondack chairs, overlooking calm waters of the channel. Lush trees and greenery frame the peaceful scene, with a small dock visible across the water, contributing to a serene outdoor atmosphere.
Guesthouse in Tilbury
4.87 out of 5 average rating, 23 reviews

Waterfront Cabin So....Romantic!!

A perfect couples get away newly built cabin near calm waters of Lake St Clair right on the channel @ Thames river, ideal for couple who enjoy their own paddleboards and kayaks even better bring your small boat and dock 10 feet from cabin! Cabin is equipped with all creature comforts ideal for 2 adults given proximity to water no children ,attached kitchenette full spacious bathroom, double comfy bed, outdoor kitchen, gazebo all included.. Bring your sandals and bottle of wine

Top guest favorite
A charming brick guest house is surrounded by lush green lawns and mature trees. The property features a rustic wagon as a decorative element, with warm lights illuminating the exterior. A spacious driveway provides easy access to the home, enhancing its inviting appeal.
Guesthouse in Essex
4.99 out of 5 average rating, 369 reviews

Wine Country Retreat w/ Hot Tub & Fire Pit

Welcome to The Vineyard Retreat, your peaceful, private escape along Essex County’s wine route between Kingsville and Colchester. This thoughtfully designed guest house feels like a private retreat, with its own entrance, outdoor living space featuring a hot tub, fire pit, and barbecue, overlooking a serene farmers’ field. Just steps from Lake Erie, you’ll be close to wineries, breweries, beaches, parks, orchards, and markets. It’s the perfect place to relax, restore, and reconnect.

The exterior of a contemporary two-story home is presented, featuring a mix of brick and stone accents. Large windows allow for ample natural light, and modern garage doors complement the design. A spacious driveway is visible, surrounded by minimal landscaping.
Guesthouse in Windsor
4.83 out of 5 average rating, 18 reviews

Welcome to the urban retreat !

Step into this brand-new, where modern luxury meets comfort and style. Unwind in your private backyard sanctuary, complete with BBQ area, perfect for warm weather gatherings.The spacious living area features a cozy fireplace, while the bathroom offer sleek sophistication.With three spacious bedrooms and in-suite laundry, this unit is perfect for relaxing and recharging. Plus, its unbeatable location puts you just steps from parks and minutes from the city's top attractions.

Top guest favorite
A spacious outdoor area showcases a lush green lawn leading to the rocky shoreline of Lake Erie. The sunset creates a gradient of soft colors in the sky. Nearby, a flower arrangement adds a touch of color, and stone pathways provide access to the seating area.
Guesthouse in Kingsville
4.98 out of 5 average rating, 43 reviews

Tranquil Lake front Guesthouse w/ king size bed.

Kick back and relax in this renovated, cozy waterfront guesthouse with an outdoor fire table and barbecue, located on the Lake Erie North Shore EPIC Wine Route. Conveniently located minutes outside of the Town of Kingsville, guests can enjoy some of the best restaurants the area has to offer. Birding guests will enjoy the short drive to Point Pelee National Park or take the ferry to Pelee Island, Canada’s most southern point. Cedar Beach is within walking distance.

Guesthouse in Kingsville
New place to stay

Cozy Cottam Guest House

Wake Up to Your Own Private Escape in Charming Cottam Discover the perfect getaway at Cottam Ridge Guesthouse, where modern convenience meets authentic village charm. Nestled on the main strip of picturesque Cottam, this intimate space offers couples and solo travelers an inviting home base with the privacy and comfort you're looking for. Whether you're seeking a romantic escape or an adventure through Southwest Ontario.

A comfortable seating area features a light-colored sofa and a wooden coffee table atop a textured rug. A brick fireplace serves as the focal point, while a flat-screen television is mounted on the wall, creating a cozy atmosphere in the open space.
Guesthouse in Windsor
4.75 out of 5 average rating, 273 reviews

Cozy 1 Bed Basement Studio Apt

Enjoy your stay in this beautiful cozy, newly remodeled studio! Conveniently located in the peaceful neighborhood of Forest Glade. Close to all amenities. 4 minutes from E.C. Row and 20 minutes drive to Ambassador Bridge. Open concept basement studio guest house with a small kitchenette and 3 piece private bathroom.

Top guest favorite
A cozy living area features a flat-screen television mounted on a neutral wall, above an electric fireplace with an ember glow. Comfortable tan armchairs are positioned alongside a circular coffee table, adorned with a plant and decorative items, inviting relaxation.
Guesthouse in Kingsville
4.97 out of 5 average rating, 36 reviews

Gem on Prospect

This gem is a new build, open concept kitchen/living room with vaulted ceilings and skylights. The bedroom has a queen size bed. Located 2 blocks from Lakeside park, Kingsville docks and Greenway nature trail. Walk to town and enjoy gourmet restaurants, bars, bakeries, wineries, breweries and boutique shopping.

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