Cottage vacation rentals in Windsor

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Popular amenities for Windsor cottage rentals

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 stars2 months 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.
Guest favorite
Cottage in Leamington
4.9 out of 5 average rating, 115 reviews

Waterfront - Hot Tub - 3Bed Cottage - Pet Friendly

AlanRating, 5 stars1 month ago
We had a great stay. Really enjoyed the views on either side of property. Great spot for birding just down at the end of the road. The hot tub was a great way to unwind and recharge after a day in the park!
Superhost
Cottage in Essex
4.95 out of 5 average rating, 63 reviews

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

SamRating, 5 stars1 month ago
Jeremy’s place was amazing! The pictures do not do it justice, it was even more beautiful in person. The walk to the beach was barely 3 minutes and the drive to nearby wineries was less than 10 minutes. The backyard space was private and comfortable. We are already hoping to travel there again!
Guest favorite
Cottage in Brownstown Charter Township
4.92 out of 5 average rating, 129 reviews

Waterfront home with amazing views & great fishing

DanRating, 5 stars5 days ago
Perfect place to stay - very clean and has great amenities. Plenty of open room in the house with an awesome backyard space. Enjoyed our stay, would return for another trip. Thank you to the hosts.
Guest favorite
Cottage in Berlin Charter Township
5 out of 5 average rating, 17 reviews

Eddie's dream on the lake

KimRating, 5 stars8 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 Leamington
4.9 out of 5 average rating, 108 reviews

Hot Tub, Sunsets and Moon lit Lakehouse!

ArthurRating, 5 stars3 weeks ago
We found Paul's place to be cozy and clean. Amenities and furniture listed are all there, and in good working order. The lakeview from the photos are exactly that - unobstructed view out to the lake. The first day we were there the weather was quite rough, so the lake looked like something from a storm movie and it was very windy. The second night was much calmer, and our kids were able to go down to the private beach which they enjoyed a lot. The wind from the first night helped a bit with the bugs but the second night it was unbearable to go out at all. We searched and found it is a common thing for the area in May. Nevertheless didn't affect us had BBQ and hot tub earlier in the late afternoon, so plan accordingly if you are in the area around this time. There are additional off-site check-in and security deposit required, including uploading a copy of your driver's license to a 3-party site. I didn't like this part but they included this in their listing so we were aware.
Guest favorite
Cottage in Leamington
4.84 out of 5 average rating, 86 reviews

East beach cottage

ChristinaRating, 5 stars2 weeks ago
My stay here was incredible. I felt very comfortable and safe. The location is absolutely amazing, I’d recommend this place to everyone. Ben was an excellent host that went above and beyond. The place came with a pass to point Pelee park which was such a beautiful place. Overall the perfect place for a little weekend get away !!!
Top guest favorite
Cottage in Wheatley
4.99 out of 5 average rating, 137 reviews

Book Wine & Sinker-Hot Tub-Lake-Pet Friendly

NadiaRating, 5 stars5 days ago
This place is wonderful! Such a sweet arrival gift for us and our pup - Deb thought of everything. All the comforts of home and super clean. Loved the hot tub and view from the kitchen. A lot of love has been put into this home and it’s a great value including park passes too! We will be back 😊

Pet-friendly cottage rentals

Top guest favorite
Cottage in Kingsville
5 out of 5 average rating, 51 reviews

Reveries on the Lake- Kingsville cottage

MarikaRating, 5 stars3 days ago
Super cute small cottage on the lake. Very good location for anyone looking to spend time in Kingsville or Leamington.
Top guest favorite
Cottage in Leamington
4.89 out of 5 average rating, 148 reviews

Erie Shores Cottages

DotRating, 5 stars3 weeks ago
Everything about this cottage was exactly what we were hoping for. It was right on the water and the sunsets were amazing. Very clean and everything we needed in the kitchen bathroom and bedrooms. Very comfortable and we loved the sunroom! The grounds were well kept too. And it was in close proximity to the ferry to Pelee Island and Point Pelee national park. I’ve already recommended this place to friends. We will definitely book this again if we are in that area in the future.
Top guest favorite
Cottage in Leamington
4.78 out of 5 average rating, 64 reviews

Cozy Cottage

SunnyRating, 5 stars1 month 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.
Superhost
Cottage in Harrow
4.89 out of 5 average rating, 38 reviews

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

DianaRating, 5 stars3 weeks ago
A very cozy cabin and great location. The cabin was a perfect place to spend time with family or friends. It was a pleasant time spent with my family. The first two days we had a pleasant weather, so we went to beach. The beach is perfect for family with kids, and has a very nice restaurant close by where we could have lunch together. Next two days, the weather changed but we gladly stayed at the cabin, and enjoyed the fire pit, barbecue by the picnic table, and Jenga (they have a big Jenga). The pool table also made the nights more special. They have bikes available but we didn’t have a chance to use it but I think they are a bonus. We will definitely come back!
Guest favorite
Cottage in Amherstburg
4.97 out of 5 average rating, 35 reviews

A Lakeside View

AnneRating, 5 stars7 months ago
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.
Top guest favorite
Cottage in Kingsville
5 out of 5 average rating, 26 reviews

Waterfront Cottage near Beach - kayaks & game room

DennisRating, 5 stars1 week ago
Creekside cottage is a quiet, peaceful place to relax and enjoy the calm and serenity of nature. The host's did a great job with the decor and ambiance of the place. It has a warm and welcoming feel to it. We stayed three nights and had a great time, (walk to the park, the beach, the bakery). This is one of the best vacation destinations out there. Thank you Lindsey and Dylan.
Guest favorite
Cottage in Amherstburg
4.89 out of 5 average rating, 87 reviews

LAKE Escape Retreat - Onsite Beach Dock Waterfront

YeuRating, 5 stars2 weeks ago
What a memorable weekend! Tim was a superhost. He was very responsive and understanding. We arrived in town Friday, hoping to do some fishing around the area before checking in. Unfortunately, the weather was very cold and windy and our check in was not until 4pm. Tim was awesome and allowed us to check in early at noon to seek shelter for us, ladies, while the men brave the windy weather to fish on the dock. FISH ON!! BEST TIME EVER!! They caught a fish every 5 minute and the feeling was intoxicating! Even some of us ladies pulled fish in!! Thank you, Tim for being so accommodating and allowing us to experience this abundant fishing experience. We will most definately be back!
Guest favorite
Cottage in Kingsville
4.92 out of 5 average rating, 77 reviews

Sauna, stunning Lake Erie view, lakefront retreat

AmandakoltonRating, 5 stars2 weeks ago
We had the best weekend there we will definitely be back and would recommend to anyone to go give it a try!

Private cottage rentals

Top guest favorite
Cottage in Essex
5 out of 5 average rating, 29 reviews

Lakefront cottage in heart of wine country

JoyceRating, 5 stars1 month ago
My friends and I wanted a weekend away just to chill and catch up. We did a wine tour on the Saturday and then hung out at the house the rest of the afternoon. The place was perfect. Beds good, well stocked kitchen and beautiful deck. Wish the weather had been warmer and not rainy - would have liked to have sat outside but it was still a great weekend in a beautiful vacation rental
Guest favorite
Cottage in Wheatley
4.88 out of 5 average rating, 94 reviews

Lakefront Family Getaway-beach nearby

StephanieRating, 5 stars2 weeks ago
A cozy spot that was great for our relaxing getaway. Quick access to town and the ferry to Pelee. Tracy was super quick to respond to any questions we had.
Guest favorite
Cottage in Leamington
4.95 out of 5 average rating, 85 reviews

Southern Exposure on Lake Erie

SandraRating, 5 stars1 week ago
We loved the place , the views are amazing. So nice sleeping to the sound of the crashing waves . We had everything we wanted and more ! We will be back
Top guest favorite
Cottage in Leamington
5 out of 5 average rating, 25 reviews

On The Rocks Lakehouse - Point Pelee, Leamington

HemangibenRating, 5 stars3 weeks ago
We had a fantastic stay at this lake house! The host was incredibly responsive and made everything easy from check-in to check-out. The view of the lake was absolutely spectacular—perfect for relaxing mornings and peaceful evenings. The house was well equipped with everything we needed, making it feel like a true home away from home. Highly recommended!
Guest favorite
Cottage in Pointe aux Roches
4.92 out of 5 average rating, 25 reviews

Charm & Style in this 2 bedroom lake front cottage

DanielaRating, 5 stars6 months ago
I booked Jenna's house for my colleague and his wife as he was there on a business trip for us. They both liked it very much and can highly recommend the accommodation and also the surrounding area.
Top guest favorite
Cottage in Kingsville
5 out of 5 average rating, 66 reviews

Unique A-Frame Cottage Steps away from the Beach!

HeatherRating, 5 stars8 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!
Guest favorite
Cottage in Leamington
4.89 out of 5 average rating, 27 reviews

On The Rocks

KentonRating, 5 stars3 weeks ago
Very nice place right on the water. The beds were comfortable and the kitchen was well stocked. Highly recommend!
Superhost
Cottage in Leamington
4.8 out of 5 average rating, 41 reviews

Point Pelee Beach House

VeraRating, 5 stars1 month ago
We really enjoyed our stay at Shannon’s cottage. We were at Point Pelee for birding and this was the perfect location. Everything was as described and we felt very comfortable. Thanks for a great week!

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