Holiday houses 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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Top Guest favourite

The exterior of a multi-story century home is showcased, featuring wooden siding and a gabled roof. Flower boxes adorn the windows, while lush greenery surrounds the property. A pathway leads to the entrance, enhancing the welcoming presence of the residence.

Home in Chardon

4.99 out of 5 average rating, 137 reviews

Avonlea Gardens & Inn - Entire House

Avonlea Inn is a century home with unique vintage charm! 3 bedrooms (upstairs - 1 king & 1 queen, main floor - 1 queen & queen pullout sofa in living room). Dining room, kitchen, & front porch. Located on same property as our native plant nursery - you are welcome to wander! Renting half the house is possible - please see separate listings for the Rose Suite (2 bedrooms on 2nd floor) or the Bluebell Suite (1 bedroom, pullout, full kitchen on 1st floor). Pets allowed only if renting entire house.

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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, 383 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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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, 242 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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Top Guest favourite

A porch with rustic wooden railings is shown, featuring two comfortable chairs. Hanging flower planters add colorful accents, while potted plants enhance the natural setting. Sunlight filters through the trees, creating a serene atmosphere in the wooded surroundings.

Cabin in Middlefield

4.98 out of 5 average rating, 221 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.

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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, 561 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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Top Guest favourite

Guesthouse in Chardon

4.96 out of 5 average rating, 346 reviews

Chardon Loft

Large private 2nd floor 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. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

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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, 779 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.

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Top Guest favourite

A cozy living space features a natural stone fireplace with a rustic wooden mantel. Two windows adorned with simple fabric shades allow natural light, while a comfortable seating area includes an armchair and a sofa, complemented by a coffee table with a chess set.

Cabin in Chardon

4.96 out of 5 average rating, 228 reviews

"Just Breathe"

“Just Breathe” is a cozy log cabin sitting on the shores of a scenic 160-acre lake. It is a peaceful place to clear your thoughts & recharge you soul. Appreciate the joy of spending time doing things that regenerate your personal strength. Whether it is boating, fishing, biking, hiking, reconnecting with nature, or learning a new skill, you can find it here. Personalized Concierge Services are available for each guest to ensure individual preferences are met for a delightful stay.

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Top Guest favourite

A welcoming exterior of a cottage is shown, featuring a well-maintained lawn. Two dogs are resting on the grass. Flowering shrubs and plants add color to the landscape. The entrance is defined by a blue door, framed by windows that allow natural light inside.

Cottage in Ashtabula

4.97 out of 5 average rating, 144 reviews

Lake Life Cottage

Pet friendly 2 story cottage with a view of Lake Erie. Located 4 miles from Geneva on the Lake and 4 miles from historic Ashtabula Harbor right on Lake Road. Over 30 wineries within 15 miles. Spend the day touring Lake Erie with Canopy Tours, fishing with DB Sport Fishing Charters, or miniature golf at Adventure Zone. Enjoy the beach or marina by day and explore the wineries or nightlife on the strip. Stroll a few doors over for a memorable meal at the highly rated Alessandro’s.

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Top Guest favourite

A rustic cabin, made of cedar, is nestled in the woods. The structure features a wrap-around deck and is surrounded by a serene pond and vibrant greenery. Purple flowers in the foreground enhance the natural setting, providing a peaceful atmosphere.

Cabin in Burton

4.94 out of 5 average rating, 200 reviews

Ma & Pa’s Romantic Cabin Fire Trail Outdoor Bath

Nestled in the Woods of Geauga County is the home of Ma & Pa’s Cabin. A Getaway perfect for the weary traveler or great vacation spot! Surrounded by mature woods. Ma & Pa’s offers a unique adventure but just like home experience. Private, Hiking/Biking Trail, Fireplace, Outdoor Wood Fire pit, Spacious Kitchen, Outdoor Bath (No Jets) including Wifi. Golfing, Skydiving, Cuyahoga Valley National Park, Nelson Ledges State Park, Amish Region. Adventure Awaits at Ma & Pa’s Cabin!

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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

4.92 out of 5 average rating, 496 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.

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Top Guest favourite

A still lake reflects the surrounding greenery, creating a serene view. Tall trees frame the scene, and the calm waters are lightly disturbed by ripples. The bright blue sky overhead provides a peaceful backdrop, enhancing the natural beauty of the secluded area.

Cabin in Rome

4.92 out of 5 average rating, 114 reviews

Quiet Cabin In The Woods

Secluded lakefront fishing cabin on 30 acres offers the very definition of a quiet oasis in the woods. This home lays at the end of a mile long private drive on over 11 acres of manicured lawn surrounded by 300 year old oak trees. The lake, only feet from your front door, contains bass, bluegill, perch and catfish offering both adults and children alike a wonderful opportunity to cast a line and relax while blue heron and eagles nest in the nearby trees.

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