Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Essex

4.91 out of 5 average rating, 267 reviews

Year 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.

Superhost

Cottage in Essex

4.89 out of 5 average rating, 184 reviews

3 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!

Guest favourite

Flat in Leamington

4.88 out of 5 average rating, 207 reviews

Park 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.

Guest favourite

Cottage in Wheatley

4.99 out of 5 average rating, 111 reviews

Book 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

Superhost

Cottage in Essex

4.93 out of 5 average rating, 154 reviews

Bright, 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.

Guest favourite

Cottage in Leamington

4.99 out of 5 average rating, 298 reviews

It'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.

Guest favourite

Home in Kingsville

4.99 out of 5 average rating, 235 reviews

La 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!

Guest favourite

Home in Amherstburg

4.96 out of 5 average rating, 109 reviews

The 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!

Superhost

Home in The Core

4.83 out of 5 average rating, 121 reviews

Couple'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.

Guest favourite

Cottage in Leamington

4.95 out of 5 average rating, 148 reviews

Sunrise 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.

Guest favourite

Cottage in Leamington

4.95 out of 5 average rating, 146 reviews

Beachfront, 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

Superhost

Cottage in Leamington

4.89 out of 5 average rating, 102 reviews

Hot 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!

Popular amenities for Windsor holiday rentals

Stay near Windsor's top sights

Little Caesars Arena159 locals recommend
Ford Field164 locals recommend
Hart Plaza66 locals recommend
Detroit Institute of Arts532 locals recommend
Belle Isle380 locals recommend
Belle Isle Beach388 locals recommend

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

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Essex County
  5. Windsor