
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.
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Other great holiday rentals in Windsor
Guest favourite

Cabin in Cortland
4.86 out of 5 average rating, 29 reviewsPeaceful Rustic Entire A-Frame Cabin in the Woods
JoanRating, 5 stars2 weeks ago
Beautiful, quiet place to stay.
Top guest favourite

Home in Madison
5 out of 5 average rating, 50 reviewsWine Country Woodland Retreat
ChristinaRating, 5 stars2 weeks ago
Amy was flexible and communicative. The house was spotlessly clean and absolutely beautiful!! The hosts have thought of every detail. The outside space was the perfect bonus! Would highly recommend and will be back!!
Guest favourite

Farm stay in Rock Creek
4.91 out of 5 average rating, 33 reviewsThe Farmhouse
LeenaRating, 5 stars1 week ago
The house was big. It was very much an old farm house. It was quiet and peaceful.
Top guest favourite

Tiny home in Kinsman
5 out of 5 average rating, 48 reviewsTiny Haven
KeithRating, 5 stars1 month ago
a great place to get away for a few days. despite some terrible weather the day before we arrived leaving most of the grounds muddy, Kathleen and her husband were well prepared to help us get to the tiny haven house mud-free! very accommodating and really enjoyed our stay
Top guest favourite

Flat in Geneva
5 out of 5 average rating, 10 reviewsGrand River Haven
ChelseaRating, 5 stars5 days ago
We stayed here after our Wedding that was about 10 minutes away. The place was beautiful and very clean. The host was super kind, responsive, and very accommodating. We even had the most delicious homemade cookies waiting for us when we arrived! When we woke up we got to enjoy the beautiful patio, it was a very peaceful and relaxing stay!! Thanks for having us!!
Top guest favourite

Farm stay in Thompson
4.93 out of 5 average rating, 57 reviewsMonarch House at Midnight Rose Farm
KimberlyRating, 5 stars2 weeks ago
Our stay at Monarch House was wonderful! It was so peaceful with beautiful surroundings at the farm. The beds in all three bedrooms were super comfy, and everyone slept great. Jacqui was so responsive and friendly. If you like staying in historical homes, this is a great one! While the charm and history of 1905 is obvious, the farmhouse has been updated with amenities to make your stay comfortable - the heaters worked great, and everyone got hot showers! The location was great if you are looking to be out in the country. But it was only a quick 15-minute drive into Geneva (we were there for an event at SPIRE). And, there were so many wineries nearby - wish we had time to visit them all! We would definitely stay at Monarch House again, and I love that a portion of the rental goes to supporting pollinators.
Top guest favourite

Home in Bristolville
4.96 out of 5 average rating, 69 reviewsB’s Sunsets & Recreation
NathanRating, 5 stars1 week ago
I cannot express how perfect of an Air BNB this was. I have stayed in many many of them across the eastern U.S. This property was second to none. It was exactly as described. Cleanliness was second to none!!! You can tell the owners have hosted for a while because they thought of EVERYTHING. Labels throughout the house. Clear instructions on everything. These host have it going on! Many could take notes. Danielle was so easy to deal with and I hope she felt the same about us. Located so close to the lake, it was exactly what we needed. If I go back to Mosquito Lake area, we will be booking again! Do not hesitate to book this property. If something is wrong, it’s a freak accident and highly unlikely. I don’t give recommendations that aren’t deserved! Thank you all for having us and lending us your property for a few days! Best wishes
Top guest favourite

Flat in Middlefield
4.94 out of 5 average rating, 78 reviewsHideaway in Amish Country
SandyRating, 5 stars3 months ago
The place was a great location in that it was a short walk to the center of Middlefield. I grew up there, so it was nice to be able to walk around the town. Rick’s place was clean and had everything I needed (coffee, couch, comfy bed, clean bathroom/shower). For those who have difficulty walking stairs, it’s important to note that you must walk up about 30 steps to get to the apartment. This was not an issue for me, but some might have difficulty with it.
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- Cuyahoga Valley National Park
- Rock and Roll Hall of Fame
- Progressive Field
- Rocket Mortgage FieldHouse
- Nelson-Kennedy Ledges State Park
- Headlands Beach State Park
- Cleveland Metroparks Zoo
- Cleveland Museum of Natural History
- Mosquito Lake State Park
- Firestone Country Club
- Boston Mills
- Memphis Kiddie Park
- Cleveland Botanical Garden
- The Kirtland Country Club
- Cleveland Ski Club
- Punderson State Park
- Lake Milton State Park
- Conneaut Lake Park Camperland
- Canterbury Golf Club
- Funtimes Fun Park
- Markko Vineyards
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- Brandywine Ski Area
- Pepper Pike Club