Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite
Farm stay in Chardon
4.87 out of 5 average rating, 374 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!

Top guest favorite
Cabin in Middlefield
4.96 out of 5 average rating, 110 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!

Top guest favorite
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, 524 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.

Top guest favorite
The exterior of the Old Postal Cottage is showcased, featuring classic red brick and a welcoming sign depicting a horse. Dual white windows are framed by seasonal decorations, including a wreath and festive bow, while a sturdy railing and balcony enhance the quaint façade.
Tiny home in Parkman
4.99 out of 5 average rating, 207 reviews

The Old Postal Cottage

*Note: feel free to inquire about availability for dates not listed as open on calendar. The Old Postal Cottage, built in the 1840s, was the Parkman post office until mid 2018. It was completely renovated, and it is now a tiny house, located within an Amish community in Northeast Ohio. It has a private entrance, and is a cozy space, perfect for a getaway in the country, with access to all major roads and an easy commute to Cleveland, Youngstown, Akron, and many tourist attractions.

Top guest favorite
The sun sets over the calm waters of Lake Erie, casting a golden reflection across the surface. Soft clouds scatter in the sky, complementing the tranquil atmosphere of the lakefront. A rocky shoreline is visible in the foreground, enhancing the natural beauty.
Cottage in Conneaut
4.99 out of 5 average rating, 102 reviews

Water’s Edge Lake House with Fabulous Views!

Enjoy lakefront sunsets in a beautiful ranch home on the shores of Lake Erie. Lakefront home minutes away from golfing and Lake Shore Park providing boat docking, fishing, beach access for swimming, picnic areas. Close to Grand River wineries, Geneva-on- the- lake, shopping, restaurants, covered bridges, public parks. Entire home has recently been updated including the kitchen and bathrooms with added game room with futon and TV. Plenty of outdoor space to enjoy games and attached deck.

Guest favorite
A cozy living space features rustic wood paneling and two comfortable wooden rockers positioned beside a small table. A sectional sofa provides ample seating, while a soft rug lies on the polished hardwood floor. Natural light filters through the window adorned with blinds.
Apartment in Madison
4.96 out of 5 average rating, 260 reviews

Cozy winery getaway with hot tub!

Relax in this cozy country garage apt. in Grand River Valley. The first stop on your winery tour is just 4 minutes away with over 30 more to explore. Visit nearby Lake Erie, Thompson Ledges, Geauga Park District Observatory, or a covered bridge. Kitchenette w/ mini fridge, microwave, Keurig & sink. Quaint bath w/ stand up shower Private keycode entry Electric fireplace King size bed Rustic wood rockers & table Pet friendly Shared access to hot tub, back yard fire pit & patio

Top guest favorite
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
4.93 out of 5 average rating, 191 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!

Top guest favorite
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, 472 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.

Top guest favorite
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, 111 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.

Top guest favorite
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.
Guesthouse in Middlefield
4.97 out of 5 average rating, 170 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.

Top guest favorite
The entrance features a bright yellow door adorned with a seasonal wreath. A pair of yellow boots rests on the stone steps, complemented by surrounding greenery. A star decoration is mounted on the wall, enhancing the welcoming entrance.
Guesthouse in Chardon
5 out of 5 average rating, 160 reviews

Private, Quiet 1 BR 1 Bath Chardon Guesthouse

Enjoy a respite at this peaceful and centrally-located, renovated guesthouse. Large 1BR w full bath. Sleep with the windows open - it's that quiet. Living room and full, eat-in kitchen. Private patio for outdoor dining. Walk to historic Chardon Square and enjoy its many festivals & activities. Easy drive to Amish country, wineries, Lake Erie and its coastal towns and beaches, The Great Geauga County Fair, 40 minutes to downtown Cleveland.

Top guest favorite
A modern two-story garage structure with two large, closed garage doors is presented. The exterior features a white facade, a steep roof, and a large window on the upper level. Snow is lightly settled on the roof, and a picket fence encircles the property.
Apartment in Chardon
4.97 out of 5 average rating, 229 reviews

1br-1bth- Furnished Oasis in Chardon

The apartment is above a detached garage. The spacious floor plan is modern and fresh, on-site laundry, a full kitchen, walk-in closet and large private bathroom, this apartment feels just like home. Long term lease is available for a discounted rate. The apartment is located on a busy street (“busy” for a small town) you will hear cars and motorcycles drive by. Please take this into consideration when booking.

Popular amenities for Windsor vacation rentals

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