Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

Superhost

Guesthouse in Chardon

Chardon Loft

Large private studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix, Disney+, Discovery+, and Paramount+. No cable channels are provided. Only 5 minute walk to a park and lake; enjoy fishing, kayaking or sailing. Only 4 miles from Alpine Valley Ski Resort & 5 miles from Mayfield Road drive-in movie theater.

$75 per night

Superhost

Home in Garrettsville

“Willow Ledge at Silver Creek”with Private Hot Tub

New Construction Modern Ranch House features rustic upscale design with beautiful cozy interiors and comfort at every turn. Stunning views await with floor to ceiling windows overlooking beautiful Silver Creek and surrounding nature. Private deck is spacious and inviting with oversize hot tub, concrete fire pit, gas grill, and outdoor dining furniture. A few minutes from great restaurants, the Brewery at Garrett’s Mill, and the coolest Coffee Shop. Perfect weekend getaway or business stay.

$218 per night

Superhost

Cabin in Cortland

Cheerful Cabin-Sleeps 5 - lake views + relaxation

This unique place has a style all its own. This adorable cabin is located steps away from Mosquito Lake, bars and restaurants, bait shops, public boat launch and minutes away from lovely wineries. Perfect for small families or couples. This cabin has been professionally designed and updated. Relax on the deck and listen to live music during the summer months. The sleeping space is a loft separated by a wall. Queen bed on one side, double bed and a single up top on the other side.

$160 per night