Guesthouse holiday rentals in Essex County

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Top-rated Guesthouses in Essex County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

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

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.

FamilyLocationParking

4.98 out of 5 average rating, 781 reviews

Top Guest favourite

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

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!

FamilyLocationBathroom

4.99 out of 5 average rating, 128 reviews

Top Guest favourite

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

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.

LocationFamilySleep quality

4.97 out of 5 average rating, 33 reviews

Guest favourite

Guesthouse in LaSalle

Our Studio is perfect for 1 to 2 guests.

Take it easy in a tranquil, safe neighbourhood; located in a convenient location, 10 min to the new Gordie Howe bridge & the 401. Essex County is home to great wineries, breweries & restaurants. Approximately 20 min to beautiful wine country, 2 min drive or 8 min walk to LaSalle’s event centre. 15 min to Caesar’s Windsor & downtown Windsor locations. 6 min to Malden Rd shopping & groceries. Whether you are looking to stay for a couple days or a couple weeks we will make your stay memorable!

LocationIndoor spacesAccuracy

5.0 out of 5 average rating, 6 reviews

Guest favourite

Guesthouse in LaSalle

Quiet, cozy private Suite w/ Separate Entrance

Quiet, private main-floor suite with a separate entrance and fully self-contained living space—ideal for one guest or a cozy stay for two. Owners occupy the front half of the home, and guests share the backyard. For a peaceful, secure stay, only registered guests are permitted unless approved in advance. Walk to the LaSalle Event Centre, skating/walking path, and Detroit River sunsets. Close to the Gordie Howe Bridge, Highway 401, and major routes. Best for respectful, low-noise guests.

LocationQuietWalkability

5.0 out of 5 average rating, 7 reviews

Top Guest favourite

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

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.

FamilyLocationKitchen

4.99 out of 5 average rating, 395 reviews

Superhost

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

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.

LocationIndoor spacesHospitality

4.79 out of 5 average rating, 19 reviews

Top Guest favourite

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

Lake Erie 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.

ValueLocationParks

4.99 out of 5 average rating, 71 reviews

A cozy single room suite is visible, featuring a plush bed covered with a grey blanket. A small kitchenette is positioned against the wall, equipped with a mini fridge and storage drawers. A private bathroom is accessed through a door, providing convenient facilities.

Guesthouse in Walkerville

ADU - private access and en-suite, in Walkerville

Welcome to our cozy single room standalone unit with a private entrance and ensuite bathroom! Nestled in a historic neighborhood, our space is perfect for solo travellers seeking a comfortable retreat. Enjoy a restful night's sleep on a plush bed and take advantage of convenient amenities. Explore local attractions easily with our central location. We look forward to hosting you!

Solo travelHospitalityCleanliness

5.0 out of 5 average rating, 4 reviews

Top Guest favourite

Guesthouse in Kingsville

Cozy Cottam Guest House

Cottam Ridge Guesthouse is a cozy space with private entrance, located between Kingsville and Town of Essex. We offer solo travellers and couples a relaxing home base to unwind and explore. Whether you’re visiting family and friends or setting out to discover the wineries, beaches, parks, you can return to a quiet night's sleep with nearby gas, breakfast, pizza and a brewery.

LocationValueAccuracy

4.93 out of 5 average rating, 43 reviews

Guest favourite

Guesthouse in Windsor

Private Guest House in South Windsor

Welcome to your private Windsor retreat, tucked away in one of the city’s most sought-after neighborhoods. Enjoy a quiet, upscale guest house with private parking, access to a relaxing backyard lounge, and everything you need for a comfortable, worry-free stay. Perfect for a night, weekend, or extended visit—book your stay and settle in.

LocationValueWi-Fi

4.93 out of 5 average rating, 96 reviews

Superhost

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

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.

FamilyValueLaundry

4.72 out of 5 average rating, 321 reviews