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 favourite

Guest house in Madison

4.95 out of 5 average rating, 164 reviews

LemonDrop 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

£118 per night
Guest favourite

Cabin in Middlefield

4.98 out of 5 average rating, 163 reviews

Forever 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

£139 per night
Guest favourite

Cottage in Willowick

4.97 out of 5 average rating, 268 reviews

Lake 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

£115 per night

Popular amenities for Windsor holiday rentals

Other great holiday rentals in Windsor

Guest favourite

Home in Garrettsville

5.0 out of 5 average rating, 294 reviews

“Willow Ledge at Silver Creek”with Private Hot Tub

7–14 Feb

£216 per night
Guest favourite

Cottage in Burton

4.92 out of 5 average rating, 117 reviews

Lakeside Cottage with Views and Charm

6–13 Dec

£149 per night
Guest favourite

Guest suite in Geneva

4.97 out of 5 average rating, 139 reviews

Lorentus' Century Home

17–24 May

£66 per night
Guest favourite

Cottage in Burton

5.0 out of 5 average rating, 103 reviews

Relax & Unwind, Lake View on Lt. Punderson Lake

6–13 Dec

£214 per night
Guest favourite

Cottage in Springboro

4.98 out of 5 average rating, 244 reviews

Cozy Country Getaway 40 wooded acres, safe, secure

3–10 May

£98 per night
Guest favourite

Home in West Farmington

4.92 out of 5 average rating, 61 reviews

The Old Firehouse

23 Feb – 2 Mar

£103 per night
Guest favourite

Flat in Burton

4.96 out of 5 average rating, 47 reviews

Maple Syrup Sugarhouse Studio Apartment

24 Apr – 1 May

£85 per night
Guest favourite

Place to stay in Middlefield

5.0 out of 5 average rating, 37 reviews

Red Maple Carriage House

8–15 Oct

£96 per night
Guest favourite

Tiny home in Kinsman

5.0 out of 5 average rating, 13 reviews

Tiny Haven

18–25 Aug

£106 per night
Guest favourite

Flat in Middlefield

4.92 out of 5 average rating, 59 reviews

Hideaway in Amish Country

12–19 Jan

£90 per night
Guest favourite

Home in Middlefield

4.88 out of 5 average rating, 24 reviews

Farmhouse Retreat

19–26 Aug

£109 per night
Guest favourite

Home in Burton

4.95 out of 5 average rating, 43 reviews

Rocking H Lakefront Cottage

9–16 Apr

£123 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Ohio
  4. Ashtabula County
  5. Windsor