Cottage holiday rentals in Windsor

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Windsor

Cottage rentals with a hot tub

Superhost
Cottage in Essex
4.95 out of 5 average rating, 94 reviews

Lakeside Hydeaway Cottage on Lake Erie w/ Hot Tub

BethRating, 5 stars1 month ago
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.
Superhost
Cottage in Essex
4.97 out of 5 average rating, 61 reviews

2-bedroom with hot tub,200 steps from the beach

BronwynRating, 5 stars3 months ago
Absolute dream place!! Wonderful neighborhood and absolutely pristine place. 5 star! One of the best airbnbs I have stayed at. Thank you!!
Guest favourite
Cottage in Brownstown Charter Township
4.92 out of 5 average rating, 124 reviews

Waterfront home with amazing views & great fishing

TerryRating, 5 stars1 week ago
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.
Top guest favourite
Cottage in Berlin Charter Township
5 out of 5 average rating, 17 reviews

Eddie's dream on the lake

KimRating, 5 stars7 months ago
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!
Superhost
Cottage in Tilbury
4.67 out of 5 average rating, 33 reviews

ENJOY WONDERFUL WATERFRONT GET AWAY

CindyRating, 5 stars4 months ago
Very beautiful location house was spotless and functional. Will stay again
Superhost
Cottage in Leamington
4.9 out of 5 average rating, 107 reviews

Hot Tub, Sunsets and Moon lit Lakehouse!

MarkRating, 5 stars1 week ago
It was exactly as advertised! Wonderful place that had everything we needed. Great view of the lake, enjoyed the back deck! The place was so clean and up to date. Would definitely come back.
Guest favourite
Cottage in Leamington
4.84 out of 5 average rating, 85 reviews

East beach cottage

KathyRating, 5 stars7 months ago
Booked Ben's place for the sunrise...it was beautiful. Place was very clean. Would highly recommend.
Guest favourite
Cottage in Leamington
4.94 out of 5 average rating, 152 reviews

Beachfront, Hot tub, Sunsets, Moonlight, Romance,

MaryRating, 5 stars1 week ago
Amazing view and beautiful home. Lovely retreat spot to take comfort. Paul and his team are great hosts.

Pet-friendly cottage rentals

Superhost
Cottage in Harrow
4.89 out of 5 average rating, 35 reviews

"That 70's Cottage" (on Lake Erie!) Free Firewood!

SteveRating, 5 stars1 week ago
“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
Guest favourite
Cottage in Leamington
4.78 out of 5 average rating, 63 reviews

Cozy Cottage

SunnyRating, 5 stars3 days ago
We had a great time at the cozy cottage. Tracey was very responsive and friendly in her communications. And we really appreciated the access to Point Peelee national park.
Guest favourite
Cottage in Essex
4.79 out of 5 average rating, 149 reviews

Lakeside getaway

SierraRating, 5 stars2 weeks ago
Devon’s place was great for a girls weekend trip! We felt comfortable and right at home, and we enjoyed the area for being peaceful. Looked like the photos and had everything we needed for the weekend! Would stay again!
Guest favourite
Cottage in Essex
4.93 out of 5 average rating, 127 reviews

North Shore Retreat

MelissaRating, 5 stars3 months ago
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!
Guest favourite
Cottage in Leamington
4.94 out of 5 average rating, 109 reviews

2thePoint-Fireplace & Lakeviews

KarenRating, 5 stars1 week ago
What a beautiful cottage in a perfect location near the entrance to Point Pelee National Park and close to lovely conservation areas to explore and Leamington to enjoy our much loved authentic Mexican restaurants. Looking forward to coming back here!
Guest favourite
Cottage in Lakeshore
4.89 out of 5 average rating, 81 reviews

Rochester Place Golf Club& Resort #715 (#16) WIFI

YolandaRating, 5 stars8 months ago
by far the most beautiful Cottage, backyard onto the golf course. beautiful grass and trees, lots of shade, great place for kids to play, no water to worry about. home was beautifully furnished and pristine clean. lots of bedding and towels to choose. easy walk to the pool. we had such a great vacation.
Superhost
Cottage in Amherstburg
4.88 out of 5 average rating, 83 reviews

LAKE Escape Retreat - Onsite Beach Dock Waterfront

AnnaRating, 5 stars4 months ago
Charming cottage with a beautiful lake view. Has everything you need from kitchen utensils to board games.
Top guest favourite
Cottage in Wheatley
4.97 out of 5 average rating, 74 reviews

Pura Vida Beach House-100 ft. of Private Beach

EdRating, 5 stars6 months ago
Beautiful house , lots of things to do. Great games and movie set up, and an absolutely amazing view. If you are looking for a place to relax , and unwind this is the place. Amazing lake view to see wonderful sunrises and sunsets. Hosts were friendly, helpful right from the start of the process through the end of our visit.

Private cottage rentals

Superhost
Cottage in Leamington
4.95 out of 5 average rating, 93 reviews

A Stone’s Throw....from the beach, marina & ferry

JakeRating, 5 stars8 months ago
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
Guest favourite
Cottage in Kingsville
4.8 out of 5 average rating, 15 reviews

Cedar Island Sandbox

SuzanneRating, 5 stars7 months ago
Another great stay! When the weather didnt co-operate we checked out the local wineries and had an amazing lunch at Coopers Hawk. Golfed at Kingsville Golf and Country Club that was just 5 minutes up the road. We had fun kayaking in the waves and campfires on the beach! Thanks again Jeff!
Guest favourite
Cottage in Leamington
4.81 out of 5 average rating, 42 reviews

3 bedroom Lake House

JimRating, 5 stars8 months ago
We had a great stay at Dragana’s lake house. On nice days we had good access to the lake. On stormy days we enjoyed the waves crashing on the rocks below the deck. The house was fully equipped with everything we needed.
Top guest favourite
Cottage in Kingsville
5 out of 5 average rating, 20 reviews

Creekside Cottage - Waterfront fun steps to beach!

PaigeRating, 5 stars1 week ago
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!!
Guest favourite
Cottage in Kingsville
5 out of 5 average rating, 16 reviews

Lake front Guesthouse w/ king sz bed.

SanyaRating, 5 stars2 weeks ago
This was a perfect little spot if you’re planning to visit Point Peele. Aime’s place was nice and cozy and perfect view of Lake Erie. The guess house was very well equipped with everything. It’s literally at the waterfront and the sounds of the waves crashing on the shore was exactly what I needed to relax. This is super close to a lot of nice restaurants in Kingsville. Thanks again for the local goodies, we’ll be back again.
Top guest favourite
Cottage in Kingsville
5 out of 5 average rating, 27 reviews

Bella Vista - Cedar Island Kingsville, Lakefront!

SarahRating, 5 stars6 months ago
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!
Top guest favourite
Cottage in Leamington
4.92 out of 5 average rating, 88 reviews

Lakefront Getaway

YicongRating, 5 stars1 week ago
Sandra’s house is absolutely a perfect place to stay for anyone visiting the area. The views on both sides of the house are breathtakingly beautiful. You will have the beautiful Lake Erie on one side where you can sit by the water and enjoy the sunrise or on the other canal side you can see turtles and so many beautiful birds and enjoy a equally stunning sunset. The house itself is extremely clean and equipped with everything we need. It is also very close to the Point Pelee national park or the ferry terminal, and so many other nice places for you to explore. Communications with the hosts are very smooth and highly recommended this place to everyone
Top guest favourite
Cottage in Kingsville
5 out of 5 average rating, 66 reviews

Unique A-Frame Cottage Steps away from the Beach!

HeatherRating, 5 stars7 months ago
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!

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