
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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Cottage in Essex
4.91 out of 5 average rating, 267 reviewsYear Round Hot Tub & Beautiful Views Cottage
Welcome to the Cozy Lakeside Cottage! Located within the village of Colchester, right on Lake Erie, nestled in the middle of Essex Wine Country. This cottage features 4 beds (A queen bed in the primary bedroom, one bunk bed with a queen base and a full upper bunk in the 2nd bedroom, plus an additional murphy bed on the main floor) Full kitchen, indoor dining, outdoor dining, 4 person hot tub & stunning views! Colchester Beach, Restaurants, Park & Marina just steps away! A truly relaxing escape.

Cottage in Essex
4.89 out of 5 average rating, 184 reviews3 Bdr Toes In The Sand Beach Cottage on Lake Erie
Located in the heart of wine country, on a Lake Erie sandy beach with great views, family-friendly activities, restaurants and dining. You will love the high ceilings, panoramic views, comfy beds, hearing the waves on the beach, the feeling of your toes in the sand with a cool drink in your hand. This retreat is great for couples, solo adventurers, business travellers, and families (with kids). There is a cozy gas fireplace with 4K TV, Netflix, wifi, & full kitchen. Your Haven awaits you!

Flat in Leamington
4.88 out of 5 average rating, 207 reviewsPark Bungalow #4 - Seacliff Beach Suites
Welcome to the Park Bungalow in Leamington, Ontario. Beautifully renovated flat in Leamington's best location! Welcoming pets and nestled beside Seacliff Park and Beach, and abundant restaurants, this listing has everything you need. A fully equipped kitchen and large living area make this an ideal place for your visit. Front and back yard for your use with large private paved area (fires and loud noises not allowed - please respect our neighbors). Two cars maximum. Tv's in all rooms.

Cottage in Wheatley
4.99 out of 5 average rating, 111 reviewsBook Wine & Sinker-Hot Tub-Lake-FREE NIGHT
FREE NIGHT!!! Book 2 weeknights and get a third weeknight FREE!! Valid Feb 2-Mar 27, 2025. Send me an inquiry!! Welcome to our serene lakeside retreat, the perfect escape for your winter getaway. This cottage offers breathtaking views and a warm inviting atmosphere. Relax in the lake view hot tub or sip your favourite wine around the fire on those chilly autumn nights. Close to Wineries and many restaurants. PET FRIENDLY!! Point Pelee and Hillman Marsh are minutes away, passes included

Cottage in Essex
4.93 out of 5 average rating, 154 reviewsBright, Peaceful Lakefront ~Sunporch, BBQ, firepit
Welcome to A Day at the Lake! Relaxation, a cozy space and comfortable beds located here. Enjoy the light and airy feel of this lakefront cottage with plenty of natural light and cool breezes off Lake Erie. Located on Clark Beach in Harrow; near wineries, beaches, conservation areas, cycling and paddling routes. Welcome birders, beach goers, winery/brewing enthusiasts, cyclists and runners. Spring and summer dates book fast so be sure to reserve early to avoid disappointment.

Cottage in Leamington
4.99 out of 5 average rating, 298 reviewsIt's a 'Shore' thing - Executive Retreat
Year round beautiful upscale 3 bedroom modern, chic cottage. sleeps 6. Outstanding views of lake. Relax in the Hot tub, Gas fireplace for cool nights. Outdoor gas fire table. Fabulous for romantic getaways, GIRLS 'just wanna have fun' weekends, or friends gathering .Beach/boat launch in walking distance. Gas BBQ, central A/C, wifi. Even swings overlooking the lake!! Great area for Wineries, Birding, Fishing, sightseeing, Pelee Island, Conservation areas. EV outlet on property.

Home in Kingsville
4.99 out of 5 average rating, 235 reviewsLa Perla - Lakefront Retreat in Wine Country!
Indulge in the stunning views of Lake Erie while relaxing at a one-of-a-kind vacation property. Experience the perfect harmony of contemporary comfort and vintage allure in every corner of our space. Nestled in Canada's most southern wine region, we're minutes from craft breweries, golf, dining, and Point Pelee National Park. Enjoy zero-contact check-in, pristine cleaning, luxurious linens and a chefs kitchen! Contact us today to begin planning your unforgettable getaway!

Home in Amherstburg
4.96 out of 5 average rating, 109 reviewsThe Lake House Ontario
Located at the start of the award winning EPIC Wine Trail, modern home 2 sides open to beautiful Lake Erie. Amazing sunset views from the hot tub. Sleeps 6 w 2 bdrms both w super comfy beds & 1 dbl pull out sofa bed, 1.5 baths, hardwood, gourmet kitchen, cozy gas fireplace, jacuzzi tub, gas BBQ, gas fire table - perfect for fun, romance or celebrating friendships. Beach just steps away. Canada's southernmost tip Point Pelee National Park, golf, museums, all just minutes away!

Home in The Core
4.83 out of 5 average rating, 121 reviewsCouple's Romantic Retreat with hot tub, fire pit.
Romantic and soothing discreet hideaway. Come to relax, reunite and enjoy the night. This beautiful unit features: -private backyard Oasis with Hot tub, cedar Gazebo, outdoor Tv and sound bar, accent lighting, bbq and fire pit. -king size bed; -couple's spa shower; -massage table -fully stocked chef's kitchen; -private garage parking; -nearby parks and trails; -plus all of the comforts of being in the city. Everything you need to enjoy a restful and relaxing weekend away.

Cottage in Leamington
4.95 out of 5 average rating, 148 reviewsSunrise Retreat - Lakefront Cottage w/ Hot Tub
This beautiful tranquil cottage is the perfect escape from your everyday frenzied life. Perfect for a couple's getaway, girls’ weekend or just a space to be on your own. Located on a quiet road, close to beaches, walking trails, fishing harbour, restaurants, wineries & breweries. Well behaved dogs are welcomed. Renters must be over the age of 30. Annual Family Pass to Point Peele National Park is available for all guests to use.

Cottage in Leamington
4.95 out of 5 average rating, 146 reviewsBeachfront, Hot tub, Sunsets, Moonlight, Romance,
Check out this magnificent cottage on the Shores of Lake Erie. This cozy, 2 bedroom waterfront property is sparkling clean and extremely comfortable. It's the perfect getaway for any nature lover! It's nestled in a quiet lakefront area with a beach when water levels are not high, and a relaxing hot tub with a view of the stunning sunsets over Lake Erie. A stones throw from Point Pelee National Park & Hillman Marsh

Cottage in Leamington
4.89 out of 5 average rating, 102 reviewsHot Tub, Sunsets and Moon lit Lakehouse!
On the pristine waters of Lake Erie, you will find this stunning lakefront escape and pure perfection!! Casa del Lago provides serenity on the shores of one of Ontario's Great lakes... Lake Erie. This contemporary home with its coastal décor, is one of Leamington's most premiere private beachfront home with very spacious living area over two floors, Accommodates 8, has 3 Bedrooms, 2 full Bathrooms and a HOT TUB!
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Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Home in Amherstburg
4.96 out of 5 average rating, 76 reviewsErie View Lakehouse - Serene and Spacious

Cottage in Leamington
4.98 out of 5 average rating, 40 reviewsSunsets by the Bay - Your Waterfront Oasis

Townhouse in Windsor
4.96 out of 5 average rating, 25 reviewsExecutive Home Rental

Loft in Wyandotte
5 out of 5 average rating, 4 reviewsLoft, Open Concept, Balcony 2 Bed, Pool Gym, Wifi

Cottage in Kingsville
5 out of 5 average rating, 60 reviewsStunning Beachhouse with 200ft of Private Beach

Flat in Grosse Pointe Park
4.86 out of 5 average rating, 14 reviewsVilla del Lago Grosse Pointe Park 1 King 2 Queens

Cottage in Belle River
5 out of 5 average rating, 43 reviewsUrban Cottage Adorable Shabby Chic Getaway for 2

Home in Allen Park
5 out of 5 average rating, 30 reviewsThis is your comfortable "home away from home"!
Quick stats about holiday rentals in Windsor
Total rentals
1.5K properties
Total number of reviews
74K reviews
Family-friendly rentals
610 properties are a good fit for families
Pet-friendly rentals
390 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
870 properties have a dedicated workspace
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