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.
Guest house in Madison
4.95 out of 5 average rating, 164 reviewsLemonDrop Lake-Front Cottage
Fully remodeled in 2023 LemonDrop Cottage is a Lake-Front property, with direct access to Lake Erie. Lake viewable from Kitchen or Bedroom windows. Mar-2023 all New Windows, Bathroom doubled (2x) in size, new 12K AC. 2021-Hickory hardwood floors,, shower, hot water heater, oven, kitchen table/chairs, king size mattress, sofa-bed, BBQ grill (propane provided), and fire pit with wood provided. Built in 1949 as a fishing cottage, adorable Lake-Front Cabin with private stairwell down to the water.
7–14 Mar
Cabin in Middlefield
4.98 out of 5 average rating, 163 reviewsForever Spring Cabin
This is a beautiful, brand-new cabin in a quiet wooded setting with nature trails in historic Mesopotamia, Ohio. We are about 45 minutes from Youngstown and Cleveland. Amenities include coffee, tea, juice, soda, cereals, snacks, pancake mix, and even maple syrup gathered in our own local woods. Relax and unwind at the end of the day in our whirlpool for two. Or sit on the porch and enjoy the peaceful surroundings of nature. Continental breakfast only. Outdoor campfire with firewood provided.
8–15 Jul
Cottage in Willowick
4.97 out of 5 average rating, 268 reviewsLake House with Amazing Views
Amazing location right on Lake Erie. This cozy lake house has a large kitchen, full bathroom and a living room/bedroom with king-size bed. The cottage is off by itself so you can enjoy your seclusion, but we live about 200 feet away so we can assist you if you need us. Enjoy a morning coffee on the deck while watching nature, spectacular sunsets on the private patio, and falling asleep to the sounds of the lake. You will be blown away by the beauty and peacefulness of this amazing cottage.
28 Oct – 4 Nov
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Home in Garrettsville
5.0 out of 5 average rating, 294 reviews“Willow Ledge at Silver Creek”with Private Hot Tub
7–14 Feb
Cottage in Burton
4.92 out of 5 average rating, 117 reviewsLakeside Cottage with Views and Charm
6–13 Dec
Guest suite in Geneva
4.97 out of 5 average rating, 139 reviewsLorentus' Century Home
17–24 May
Cottage in Burton
5.0 out of 5 average rating, 103 reviewsRelax & Unwind, Lake View on Lt. Punderson Lake
6–13 Dec
Cottage in Springboro
4.98 out of 5 average rating, 244 reviewsCozy Country Getaway 40 wooded acres, safe, secure
3–10 May
Home in West Farmington
4.92 out of 5 average rating, 61 reviewsThe Old Firehouse
23 Feb – 2 Mar
Flat in Burton
4.96 out of 5 average rating, 47 reviewsMaple Syrup Sugarhouse Studio Apartment
24 Apr – 1 May
Place to stay in Middlefield
5.0 out of 5 average rating, 37 reviewsRed Maple Carriage House
8–15 Oct
Tiny home in Kinsman
5.0 out of 5 average rating, 13 reviewsTiny Haven
18–25 Aug
Flat in Middlefield
4.92 out of 5 average rating, 59 reviewsHideaway in Amish Country
12–19 Jan
Home in Middlefield
4.88 out of 5 average rating, 24 reviewsFarmhouse Retreat
19–26 Aug
Home in Burton
4.95 out of 5 average rating, 43 reviewsRocking H Lakefront Cottage
9–16 Apr
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