Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Rental unit in The Core

4.94 out of 5 average rating, 205 reviews

OLDE WALKERVILLE Windsor Ontario

Do you need a nice quite, non-shared clean place to stay ? This cute one bedroom, living room /sleeper sofa, kitchen, full bath (washer/dryer 6 nights + ) Located on the second floor, above our family home, is ready for you to enjoy your stay. In Olde Walkerville, walking distance to restaurants, pubs, boutiques and, the river with walking and bike paths along with summer activities. Short drive to the Casino, Chrysler Theatre / St. Clair Arts, U.S.A Boarder, down town Train Station.

Guest favourite

Farm stay in Essex County

5 out of 5 average rating, 100 reviews

The Fir&Feather Tree Farm 1Bedroom Suite & Hot tub

A unique and tranquil wooded getaway nestled on a 16 Acre working Christmas tree farm, 15 minutes from Windsor and surrounding towns. This private lower suite, part of the main house has its own entrance and space for up to 4 people. Open concept Kitchen/Living room with electric fireplace,2 futons/double beds with memory foam mattresses, Queen Juno mattress in bedroom and 3 piece bath. Enjoy a private furnished patio w/firepit or relax in a private hot tub (netted) at a second furnished patio

Guest favourite

Cottage in Leamington

4.96 out of 5 average rating, 123 reviews

Bird’s Eye View Lake House with Hot Tub

Our beautiful Lake House offers a bird’s eye view of Lake Erie. Situated steps away from the most southern point of Canada, Point Pelee National Park. (Family pass included with stay) Relax and enjoy our fully furnished cottage that offers all the required amenities for an amazing stay! This property is in a great location! Close to Leamington’s Seacliff Beach, Marina and Pelee Island Ferry. Paddle board and kayak rentals, go carting and golfing just up the street! Outdoor security cameras added

Guest favourite

Guest house in Kingsville

4.96 out of 5 average rating, 226 reviews

Cozy Kingsville Country Guest House

Enjoy your stay in this cozy guest house on the main strip of the charming village of Cottam, within the town of Kingsville. This attached suite will be all for you. Separated from the main house with your own private entrance in the front and rear. Relax on the spacious deck overlooking the lush green mature treed backyard, roast marshmallows at the fire pit or take a nice nap on the hammock. Located a short drive to downtown Kingsville, beaches, wineries, restaurants, craft breweries and more!

Guest favourite

Guest house in Kingsville

4.98 out of 5 average rating, 620 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.

Guest favourite

Cottage in Essex

4.93 out of 5 average rating, 341 reviews

Your Soulstice Studio

Become one with nature in this cozy cottage with an expansive view of the lake. Let yourself be absorbed by the sound of waves, birds and silence in the early morning hours. Sudden urge to do some yoga? No problem you have mats, blocks and bolsters to fulfill you ever stretching need! Your Soulstice is an up and coming yoga and massage studio that has been 2 years in the making. Now that it’s ready to open it’s doors, it needs a wee income to repay the “bank of mom” to show my appreciation! ♥️

Guest favourite

Guest house in Essex

4.99 out of 5 average rating, 307 reviews

Private Wine Route Getaway with Hot Tub

The heart behind The Vineyard Retreat is to help our guests relax, restore, and reconnect. Located on County Road 50 we're conveniently placed on the wine route between Kingsville, Colchester, and Harrow. Our guest house is steps away from Lake Erie and close by to wineries, breweries, restaurants, tours, fruit stands, national parks, conservation areas, beaches, orchards, golf courses, bike paths, and more. Read more about what our guest house has to offer in the detailed description below.

Guest favourite

Home in Kingsville

4.95 out of 5 average rating, 171 reviews

Heritage Lakehouse

Unwind at this modern lake house situated right on Lake Erie. The house was built with high ceilings and exposed raw steel accents throughout. Enjoy a stunning view of lake Erie from both bedrooms or through the 14 ft glass wall in the living room. The kitchen boasts all new appliances, quartz countertops and all of the cooking supplies needed. The house is located in between two public beaches and offers its own access into the lake. Wineries, Pelee Island, restaurants and golf courses.

Guest favourite

Cottage in Lakeshore

5 out of 5 average rating, 119 reviews

Beau Chalet de Pointe-aux-Roches (No Cleaning Fee)

Bienvenue / Welcome to the village of Pointe-aux-Roches / Stoney Point in Lakeshore, Ontario. Available May thru October, this cozy lakefront cottage-home is fully furnished for your comfort on the southeastern shore of Lake St. Clair, offering beautiful summer sunrises and sunsets. Shallow and warm Lake St. Clair, part of the Great Lakes system, is the connector lake between Lakes Huron and Erie, and has among the largest variety of fresh-water fish and aquatic species in the world.

Guest favourite

Guest suite in Kingsville

4.99 out of 5 average rating, 118 reviews

Shoreline Serenity, Private Suite

Due to Covid-19 I have extended the minimum stay to 3 nights and time between check-out and check-in to 24 hours to ensure proper disinfection. I have added an air purifier that recycles the air every 3 hours. Cozy, clean and comfortable open concept suite located on the beautiful shores of Lake Erie just one mile from downtown Kingsville where you will find excellent restaurants and eclectic shopping. The suite has its own entrance so that you have complete privacy during your stay.

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 332 reviews

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from late March to early November at 32°C (90°F). The hot tub is open year round.

Guest favourite

Home in The Core

4.92 out of 5 average rating, 116 reviews

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Welcome to our updated 2 bed 1 bath upper unit in downtown Windsor! With a fully equipped kitchen including stainless steel appliances & quartz countertops and a 65in TV with Netflix in the living room, this apartment has everything you need for a comfortable stay. Located near transit, shopping, and restaurants. This location is on a quiet block just minutes walk to the heart of downtown. Book now for a cozy and convenient home-away-from-home experience!