
Cottage vacation rentals in Windsor
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Windsor
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Lakeside Hydeaway Cottage on Lake Erie w/ Hot Tub
Joe and Christina’s place is beautiful and very relaxing. They have thought of everything to make sure their guest have all that is needed with great supplies of towels, kitchenware, etc. They were a great host always responding in good timing and accommodating our needed request to extend days.

2-bedroom with hot tub,200 steps from the beach
Absolute dream place!! Wonderful neighborhood and absolutely pristine place. 5 star! One of the best airbnbs I have stayed at. Thank you!!

Waterfront home with amazing views & great fishing
The stay went very well. There are multiple options for fishing and places to launch a boat. I would definitely recommend this for a vacation for with all the activities to be had in the area. We encountered friendly people in the area and with shopping and restaurants close by it made our time there a memorable one.

Eddie's dream on the lake
Eddie greeted us warmly and showed us how the house worked. I was there for a dog show it was absolutely perfect for that! Everything we needed was right there and it felt a very safe comfortable dog friendly area!

Year Round Hot Tub, The Beach House
Perfect communication, all question answered had of the booking,you get A+service for your money at this place!!! Clean and comfortable!!

Moe’s on the Lake: 2 bedroom waterfront cottage
Was the best Airbnb we have ever done. The host thought of everything and the house was equipped with everything need for a perfect stay. Stephanie was very responsive to all our questions. Definitely coming again.

Beach House w/Sauna in Winery Heartland
This home is in a great location - very close to area wineries and other local spots. It's very well appointed with kitchen, bed and bath items, as well as games and things to do. Beds were comfortable and the home's design and decor is very modern and tasteful.

Yellow Cardinal Lake Cottage
We had a great stay at the Yellow Cardinal cottage. Perfect if you want a quiet getaway close to the beach. The cottage had everything we needed and space for our family of 4 and the grandparents. AC units worked great as it was very hot when we visited. Wish we could have stayed longer. We hope to return next summer.
Pet-friendly cottage rentals

Reveries on the Lake-lakefront Kingsville Cottage
Cottage was clean and quiet had beautiful view of the lake with ample seating. The beds were very comfortable, Crystal provided a bottle of local wine along with some snacks. Over all a very nice place to stay lots of local amnesties close by as well as great restaurant from coffee to great local eateries. Over all a great place. Tim and Lynne

A Lakeside View
A GEM BY THE LAKE - With its lakeside location in a quiet neighbourhood, Rosanne’s property is super welcoming with a well equipped, large kitchen-cum-dining space, facing north, which is open to the south (back) great room, with its comfy sofas and chairs, games equipment and desk with brochures of local area points of interest, maps, etc. Through floor to ceiling windows of the great room, you’ll be treated to magnificent views of the lake inviting you onto the outdoor verandah to enjoy the sights and sounds (sunrises, sunsets) that’ll wow you! The second floor main suite is idyllic - a huge south-facing room with loveseat, ensuite bathroom, humongous closet and a balcony with comfy seating. Two more bedrooms (north facing) are on 2nd floor, with a 4th downstairs (west-facing). Another bathroom (east side) is also downstairs. Every space is extremely clean, well decorated but not cluttered. One of THE best homes we’ve experienced. Thank you Rosanne for hosting us and our pups.

"That 70's Cottage" (on Lake Erie!) Free Firewood!
“That 70s Cottage” was the perfect choice for a quiet long weekend getaway. As the cottage is pet friendly, my spouse & I brought our two cats who were able to enjoy the vacation with us. The location is prime with a beautiful view of Lake Erie right out of the front window. We would absolutely recommend booking this unique & cozy cottage to anyone, as we will surely be rebooking. The hosts are incredibly kind- even offering a later checkout time on checkout day- which was a wonderful bonus. Thank you again Bill & Megan for the wonderful stay! Cheers! Briana & Steve Johnson

North Shore Retreat
Had a great weekend here, it’s a gorgeous house with unbeatable views. So glad we stumbled on this gem, highly recommend it, even in the winter where the ice on the lake was beautiful to watch!

Creekside Cottage - Waterfront fun steps to beach!
This place was great! We went for my husband's birthday and we loved kayaking and walking to the beach. We made s'mores at the fireplace and sat near the dock in the morning to have coffee and tea. Lots of cute fish, birds, bunnies in the area. We can't wait to come back to Kingsville and we would stay here again!!

LAKE Escape Retreat - Onsite Beach Dock Waterfront
Charming cottage with a beautiful lake view. Has everything you need from kitchen utensils to board games.

Sauna, stunning Lake Erie view, lakefront retreat
Wished we could’ve stayed longer! Beautiful little spot on the lake. Had everything we needed and the hosts did a great job of providing all the information needed and more! Would definitely stay here again if we’re out this way!!

On The Rocks
Great space for our family of 5. Short stay for us but would have been great for a few more nights, especially into the warmer weather, being right on the water.
Private cottage rentals

A Stone’s Throw....from the beach, marina & ferry
Staying at the cottage was a great home away from home , Kathy and Bill had everything you would need and more. There is a lot to do and is in walking distance of a lot of amenities around the waterfront area of town. I would recommend this place to family and friends anytime someone wanted to visit Leamington

Lake Life Cottage
This home exceeded our expectations. We felt right at home, very comfortable and relaxed. There were so many little touches like a bottle of wine from a local winery, slippers we could use and take home, snacks, sleep mask etc. The home was super clean. Sitting on the deck looking at the lake was so beautiful and peaceful. During our stay, we needed to contact Teresa. I was very impressed with how quickly she responded. I highly recommend this home and host.

Beach House Point
We had a perfect long weekend stay. Beautiful property, super close to Point Pelee and good options for restaurants nearby. There’s a great playground for kids within walking distance, across from Freddy’s where you can stop in for some ice cream. The only thing we found a bit tricky were the sloped ceilings in the bedrooms on the second floor. We’re average height and still bumped our heads a few times so we just had to be extra careful while upstairs.

On The Rocks Lakehouse - Point Pelee, Leamington
My family and I had a wonderful Labour Day long weekend at the cottage. From playing card games at the kitchen table, to watching the stunning sunset views around the fire pit! Heathers cottage has all that you could need. Her fully stocked kitchen was so helpful with our family breakfasts and dinners. The rooms were clean and cozy. She even included a thoughtful welcome board of yummies and bathroom goodies! The family parks pass to Point Pelee was a bonus! Not to mention all the board games (coming from a family of gamers we appreciated the collection). The 90s game and the giant tower of jenga were a hit :) Heather is a 5 star host and is quick to respond to any questions we had. Thank you for accommodating my family and making us feel at home!

Bella Vista - Cedar Island Kingsville, Lakefront!
My sister and I recently spent a weekend at Bella Vista. The cottage is perfectly situated on a peaceful street, and the space was ideal for relaxing, reading, cooking, and listening to the waves rolling in. Tony and Mary-Jo were very attentive and helpful. We would definitely book it again!

Unique A-Frame Cottage Steps away from the Beach!
We had a lovely stay at Bustersplace! It was close to beautiful wineries, local shops and restaurants and the beach just as described. The house was beautifully decorated and very comfortable! We enjoyed cooking on the grill, playing bocci ball in the backyard and relaxing with a movie at the end of the day. Kingsville was a great addition to our vacation and this home was the perfect place to stay!

★Sunrise Beach House★ Epic Sun, Sand & Sea getaway
First off, this cabin is just like the pictures. It is adorable and fun. The backyard was even larger than I expected! The cabin was super clean. It smelled so fresh and clean when we walked in. There were plenty of towels for us to use. The fireplace and tvs were easy to use. There was everything you could need for this place and that was so nice. The decor is super adorable and decoration goals. The location is out of the downtown but only about 5 minutes to there. It’s quiet. We stood on the beach and couldn’t believe how there was NOTHING but the wind. Not even barking dogs. It’s a true paradise. Thanks for sharing your home with us.

Point Pelee Beach House
Amazing views! Peaceful too. The property is beautifully furnished and decorated. Appreciated all the little extras like tea , coffee , toothpaste etc. BBQ needs some TLC. Thank you for a great time
Destinations to explore
- Detroit Vacation rentals
- Cleveland Vacation rentals
- Ann Arbor Vacation rentals
- Grand Bend Vacation rentals
- Toledo Vacation rentals
- Sandusky Vacation rentals
- Lansing Vacation rentals
- Sarnia Vacation rentals
- Chicago Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Fitness-friendly rentals Windsor
- Apartment rentals Windsor
- Loft rentals Windsor
- Rentals with lake access Windsor
- Waterfront rentals Windsor
- Rentals with a patio Windsor
- Rentals with a fireplace Windsor
- Rentals with a fire pit Windsor
- Rentals with an EV charger Windsor
- Private suite rentals Windsor
- Rentals with pools Windsor
- Rentals with a washer and dryer Windsor
- Rentals with beach access Windsor
- Condo rentals Windsor
- Kid-friendly rentals Windsor
- Smoking-friendly rentals Windsor
- Pet-friendly rentals Windsor
- House rentals Windsor
- Rentals with a hot tub Windsor
- Rentals with outdoor seating Windsor
- Rentals with breakfast Windsor
- Cottage rentals Essex County
- Cottage rentals Ontario
- Cottage rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Comerica Park
- Michigan Stadium
- Wesburn Golf & Country Club
- Maumee Bay State Park
- Oakland Hills Country Club
- Alpine Valley Ski Resort
- University of Michigan Museum of Art
- Seven Lakes State Park
- Roseland Golf & Curling Club
- LEGOLAND Discovery Center Michigan
- Ambassador Golf Club
- Detroit Golf Club
- Mt. Brighton Ski Resort
- Rolling Hills Water Park
- Franklin Hills Country Club
- Orchard Lake Country Club
- Red Oaks Waterpark
- Warren Community Center
- Water Warrior Island
- Seven Lakes Championship Golf & Estates
- Country Club of Detroit