Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite
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, 356 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
A bright living area features a comfortable gray couch and a cozy armchair. Light wood beams create a warm atmosphere, complemented by a decorative wall sign. A queen-size bed is visible in the background next to a window, with natural light pouring in.
Apartment in Burton
4.96 out of 5 average rating, 140 reviews

Maple Syrup Sugarhouse Studio Apartment

Take it easy at this unique and tranquil getaway at Butternut Maple Farm in the heart of Burton Township right by the Geauga County Fairgrounds and just miles from Amish Country. This private brand new, fully furnished smoke-free studio apartment is on the second floor of the sugarhouse with a gorgeous attached deck perfect for your morning coffee. During maple sugar season (January-March), you receive front row seats to watch and/or participate in making our award winning organic maple syrup.

Top guest favorite
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, 206 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.

Top guest favorite
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, 226 reviews

Historic Village in the Heart of Amish Country!

Located in the historic district of Burton, Ohio & the Heart of Geauga County's Amish country, newly renovated, perfect for a reunion or a getaway weekend. East of Cleveland, easy access to major highways & RV parking. Children 3 & under are FREE. See Other Things to Note, Amenities, and The Neighborhood for wonderful details to make your stay special. Don't forget to ask about early check-in and late check-out times when possible to accommodate your travel schedule (no additional charge)!

Top guest favorite
Guesthouse in Chardon
4.95 out of 5 average rating, 272 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.

Guest favorite
An open-concept living space features wood-paneled walls and a warm wooden floor. A spacious sectional sofa is situated across from a large wall-mounted television. A dining area with dark chairs surrounds a long table, and a rustic coffee table made from natural wood is placed on a textured rug.
Cabin in Cortland
4.97 out of 5 average rating, 194 reviews

Cheerful Cabin-Sleeps 5 - lake views + relaxation

This unique place has a style all its own. This adorable cabin is located steps away from Mosquito Lake, bars and restaurants, bait shops, public boat launch and minutes away from lovely wineries. Perfect for small families or couples. This cabin has been professionally designed and updated. Relax on the deck and listen to live music during the summer months. The sleeping space is a loft separated by a wall. Queen bed on one side, double bed and a single up top on the other side.

Top guest favorite
The outdoor area features a spacious patio with a variety of seating options, including colorful chairs and tables. A shaded umbrella provides relief from the sun, while lush greenery surrounds the barn-like structure, leading to the entrance of the upper-level cabin.
Barn in Kinsman
4.97 out of 5 average rating, 270 reviews

Cozy Cabin in Kinsman

This is a western themed, open concept cabin. The cabin is the upper level of a barn-like structure, separated from our home by a large patio. It has a Loft and a Sleep n’ Play Hideaway for children. (The double bed inside the Hideaway is suitable for teens and even adults.) Our cozy cabin is perfect place for either a couple, a few friends or a family. It is also a wonderful place for a retreat or a place to work away from home or the office. (See photos for clarity of layout.)

Top 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, 229 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 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, 441 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.

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, 109 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 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, 149 reviews

Private, Quiet 1 BR 1 Bath Chardon Guesthouse

Enjoy a respite at this peaceful and centrally-located, newly 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
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
4.98 out of 5 average rating, 160 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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