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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Guest favourite

The image captures a lush, green pasture with several horses grazing peacefully. A wooden fence encloses the pasture, providing a tranquil rural setting, with trees dotting the landscape in the background. The sky is overcast, giving a calm ambiance to the scene.

Farm stay in Chardon

4.87 out of 5 average rating, 389 reviews

Bonnie's Guesthouse @ Peridot Equine Sanctuary

***ALL PROFITS SUPPORT THE HORSES OF PERIDOT EQUINE SANCTUARY*** The rustic decor and well lit space reflects the nature of our horse farm, where you can stay for a peaceful country getaway and bring your horses along! We're rural, but you'll still have easy access to lots of amenities in the wonderful nearby town of Chardon, less than 10 minutes away. Cleveland itself, currently going through a "rustbelt renaissance" is only about 45 minutes minutes West. We welcome guests of all backgrounds!

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Guest favourite

The living room features comfortable seating, including a gray sofa, an armchair, and a coffee table on a patterned rug. Natural light illuminates the space through large windows, and decorative artwork adorns the walls, creating a cozy atmosphere.

Home in Geneva

4.93 out of 5 average rating, 146 reviews

Sand V-Ball Ct w/ Vineyard Views SPIRE 5 Min

Enjoy a relaxing stay in this fully renovated 1860's 3BR/3 Full BT home. Featuring a spacious, fully stocked kitchen, outdoor gathering spaces, including fire pit, and sand volleyball court with vineyard views. The Grand Getaway is perfect for romantic getaways, girls weekends, bachelor/bachelorette parties, family vacations and more! Centrally located in the heart of The Grand River Valley within minutes from all local wineries and a short drive to GOTL. The perfect space for creating memories!

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Guest favourite

The exterior of the home is framed by lush greenery and a well-maintained lawn. A welcoming porch extends across the front, featuring a spacious seating area. The two-story structure showcases a combination of siding and brick, with tall trees providing shade and a natural setting.

Home in Windsor

4.9 out of 5 average rating, 30 reviews

Ridgeview Cottage

This restored open-concept home is nestled in Eastern Geauga County. Centrally located between Amish country and wine country, Ridgeview Cottage is a perfect place to stay before or after a celebration at Meadow Ridge Events, which flanks the property. This bright, airy home has three bedrooms, a fold-out couch in the lower level, and a glam room that is perfect for getting ready for a night out or special event. Two decks, a gas fire feature, and a gorgeous back yard complete the country feel.

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Top guest favourite

A charming yellow house is presented with a welcoming front door and multiple large windows. The landscaped garden features neatly arranged flower beds and gravel paths, framed by green grass. A clear blue sky and a few clouds are visible above the home.

Home in Burton

4.99 out of 5 average rating, 246 reviews

Historic Village in the Heart of Amish Country!

Located in the Historic District of Burton, Ohio & the Heart of Geauga's Amish country, perfect for a reunion or getaway weekend. 32 miles east of Cleveland, easy access to major highways. Children 3 & under are FREE. See Other Amenities, and The Neighborhood for more details to make your stay special. Don't forget to ask about "no-charge" early check-in & late check-out times if available! There is a generator so even if the power goes out, the house has electricity, hot & cold water always!

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Guest favourite

Cabin in Cortland

4.83 out of 5 average rating, 99 reviews

Peaceful Rustic Entire A-Frame Cabin in the Woods

WELCOME! Leave your worries behind and relax on a country road in the heart of Northeast Ohio to this clean & peaceful cabin in the woods! Feed the birds and wildlife while the coffee is brewing and a warm fire crackling with firewood (supplied). Furnished with WiFi & TVs and utensils for all your cooking needs. Conveniently located just 6 min away from Mosquito lake, 12 minutes from Starbucks, Walmart,Quaker Steak and 22 minutes from the Eastwood Mall Complex. Book your reservation today!

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Top guest favourite

Cabin in Middlefield

4.96 out of 5 average rating, 122 reviews

The Wildflower

Come enjoy this brand new cabin in a private wooded setting. Sit on the front porch swing or relax by the fireplace. Enjoy the whirlpool for two and new stylish decor with black metal railing against a backdrop of the finest craftsmenship of woodworking. This cabin was built by local Amish and Mennonite builders. There is a double reclining loveseat and a queen size pull out sofa with a memory foam mattress. We provide snacks, sodas, coffee, tea, cereal, juice, pancaKe mix & maple syrup!

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Top guest favourite

The exterior of a modern ranch house is showcased, featuring a vibrant red façade and a metal roof. A spacious deck is visible, complete with outdoor seating and a view of the nearby creek and surrounding trees. A gravel driveway leads to the entrance.

Home in Garrettsville

4.99 out of 5 average rating, 570 reviews

“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.

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Superhost

The A-Frame cabin stands among towering trees, showcasing its distinct triangular shape and large front deck. Surrounded by lush greenery, the wooden façade and black accents blend harmoniously with the natural environment, creating a sense of privacy and seclusion.

Cabin in West Farmington

4.89 out of 5 average rating, 785 reviews

The Triangle: Unplug in a Charming A-Frame

Step inside The Triangle & the outside world melts away. A wood-burning stove, exposed beams, and countless small details make this 400 sq ft A-Frame feel immediately like home. New deck (2024) perfect for morning coffee or evening stars. Nestled in Ohio's Amish Country - minutes from The Place at 534, Nelson-Kennedy Ledges, Observatory Park's dark skies, Holden Arboretum, and Burton Village. Exclusive music listening experience - a one of a kind cassette of my music available at the cabin.

LocationFamilyWifi

Top guest favourite

A tri-level house is shown, featuring a light-colored exterior with a metal roof. A well-maintained lawn surrounds the property, with a large tree in the front yard and a gravel driveway leading to a two-car garage. Trees line the background.

Home in Bristolville

4.96 out of 5 average rating, 102 reviews

B’s Sunsets & Recreation

IMPORTANT! I DO NOT ALLOW WORK CREWS OR PETS DUE TO EXCESSIVE DAMAGES. We gladly welcome all others to come stay at our family friendly renovated tri-level with all the comforts of home and a private back yard with fire pit. We are within 5 minutes of Mosquito lake boat launch and Western Reserve Greenway bike trail. We are a 15 minute drive to The Place at 534 and great wineries. It is a 30 minute drive to Amish country or the Eastwood Mall Complex and Scrappers Stadium.

LocationFamilyIndoor spaces

Top guest favourite

The exterior of a ranch-style home features a vintage sandstone façade complemented by a modern grey roof. Surrounded by greenery, the yard includes patches of grass and shrubs, with remnants of snow remaining, presenting a serene atmosphere at dusk.

Home in Madison

5.0 out of 5 average rating, 232 reviews

Sandstone Ranch

Welcome to Sandstone Ranch! This peaceful, charming 3 BR, 1.5 Bath ranch style home in the heart of the Grand River Valley is completely remodeled, combining a clean, timeless interior design with modern amenities and vintage charm. This is the BEST location in Lake County, minutes away from ALL the wineries, distilleries, restaurants, Historic Madison village, Geneva-on-the-Lake, Spire institute, I-90, Powderhorn golf course, and Steelhead fishing at the Metroparks!

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Top guest favourite

A rustic living area is featured with wood-paneled walls and a high, beamed ceiling. A patterned sofa and a recliner are positioned around a decorative area rug. A small electric fireplace adds warmth, while a TV hangs above the central seating. The room is adorned with a Christmas tree.

Cabin in Cortland

4.93 out of 5 average rating, 507 reviews

Cozy Countryside Cabin Near Multiple Wineries

Our cozy and inviting cabin, the Eagle's Nest, is nestled in a countryside setting behind Greene Eagle Winery and Brew Pub in rural Northeast Ohio. If you are looking for charm, and quiet relaxing comfort, this 384 sq. ft. cabin with exposed cedar beams is your perfect overnight or weekend retreat. Many activities available in the area with Mosquito lake nearby, bike trails, state park, golf, shopping, wineries, breweries, and restaurants within 10 to 30 minutes.

LocationFamilyEV charging

Top guest favourite

The exterior of a cottage features a welcoming entrance with a wooden deck, adorned with potted flowers. A bench provides a seating area, while greenery enhances the landscape. The cottage's siding showcases a neutral tone, and a gabled roof adds architectural interest.

Guest house in Middlefield

4.97 out of 5 average rating, 184 reviews

Little House on the Farm

The accommodation is a 2 bedroom cottage on our small farm that has been recently renovated. It is wheel chair accessible. We are in the middle of the fourth largest Amish community in the world. We are half a mile from the center of Mesopotamia, which is known for the End of the Commons General Store and the annual OX roast over the 4th of July. Cleveland and Youngstown are both approximately 45 minutes away. Lake Erie is 30 minutes north.

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