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.

Guest favorite

Guesthouse 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.

Mar 7 – 14

ﺩ.ﺇ504 per night
Guest favorite

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.

Jul 8 – 15

ﺩ.ﺇ624 per night
Guest favorite

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.

Oct 28 – Nov 4

ﺩ.ﺇ505 per night

Popular amenities for Windsor vacation rentals

Other great vacation rentals in Windsor

Guest favorite

Home in Garrettsville

5.0 out of 5 average rating, 294 reviews

“Willow Ledge at Silver Creek”with Private Hot Tub

Feb 7 – 14

ﺩ.ﺇ958 per night
Guest favorite

Cottage in Burton

4.92 out of 5 average rating, 117 reviews

Lakeside Cottage with Views and Charm

Dec 6 – 13

ﺩ.ﺇ632 per night
Guest favorite

Guest suite in Geneva

4.97 out of 5 average rating, 139 reviews

Lorentus' Century Home

May 17 – 24

ﺩ.ﺇ290 per night
Guest favorite

Cottage in Burton

5.0 out of 5 average rating, 103 reviews

Relax & Unwind, Lake View on Lt. Punderson Lake

Dec 6 – 13

ﺩ.ﺇ925 per night
Guest favorite

Cottage in Springboro

4.98 out of 5 average rating, 244 reviews

Cozy Country Getaway 40 wooded acres, safe, secure

May 3 – 10

ﺩ.ﺇ410 per night
Guest favorite

Home in West Farmington

4.92 out of 5 average rating, 61 reviews

The Old Firehouse

Feb 23 – Mar 2

ﺩ.ﺇ445 per night
Guest favorite

Apartment in Burton

4.96 out of 5 average rating, 47 reviews

Maple Syrup Sugarhouse Studio Apartment

Apr 24 – May 1

ﺩ.ﺇ355 per night
Guest favorite

Place to stay in Middlefield

5.0 out of 5 average rating, 37 reviews

Red Maple Carriage House

Oct 8 – 15

ﺩ.ﺇ422 per night
Guest favorite

Tiny home in Kinsman

5.0 out of 5 average rating, 13 reviews

Tiny Haven

Aug 18 – 25

ﺩ.ﺇ451 per night
Guest favorite

Apartment in Middlefield

4.92 out of 5 average rating, 59 reviews

Hideaway in Amish Country

Jan 12 – 19

ﺩ.ﺇ401 per night
Guest favorite

Home in Middlefield

4.88 out of 5 average rating, 24 reviews

Farmhouse Retreat

Aug 19 – 26

ﺩ.ﺇ505 per night
Guest favorite

Home in Burton

4.95 out of 5 average rating, 43 reviews

Rocking H Lakefront Cottage

Apr 9 – 16

ﺩ.ﺇ536 per night

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