
Holiday houses in Orwell
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Top-rated holiday rentals in Orwell
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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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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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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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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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“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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The Farmhouse
Built in 1885, stylish exposed beam updates, you'll enjoy this historic home in a picturesque, relaxed setting. Picnic on the spacious back porch, enjoy the sunrise and coffee in the airy sunroom/kitchen, or play board games with the entire family! New central HVAC, fast wifi, and smart tvs keeps you comfortable while there are plenty of beds and seating arrangements! The Farmhouse is the perfect family or group rental for winery and covered bridge tours, local festivals, weddings, and more!
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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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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.
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Wine Country Escape | Hot Tub • Sleeps 12
🏡 5 bedrooms 🌊 Hot tub open year round! 🛏 7 beds • 3 bathrooms • Sleeps 12 🌳 Huge backyard w/ fire pit (firewood provided!) 🍳 Fully equipped kitchen • BBQ grill 🍽 Dining table for 12 🎥 Smart TV's • Roku + Spectrum 💻 Desk for remote work 👶 Pack n' Play for little ones 🚗 Driveway parking for 5+ cars 🐾 Pet-friendly 🛋 Minutes to wineries, Lake Erie, and SPIRE Spacious, stylish, and close to everything — this Geneva home is the ideal group retreat in Ohio wine country.
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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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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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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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Popular amenities for Orwell holiday rentals
Other great holiday rentals in Orwell

4 Bedroom l Grand River Wineries I Spire I GOTL
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B’s Sunsets & Recreation
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Juniper Cabin | Hot Tub, Pond + Fire-pit, A-frame
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Peaceful Rustic Entire A-Frame Cabin in the Woods
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Cozy 3 Bedroom at the “Queen 45”
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The Horse & Harness-Enjoy Root Beer on the Porch
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Grand River Haven
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Monarch House at Midnight Rose Farm
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Destinations to explore
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- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Progressive Field
- Rock & Roll Hall of Fame
- Headlands Beach State Park
- Cleveland Browns Stadium
- Case Western Reserve University
- Cleveland Metroparks Zoo
- Mosquito Lake State Park
- Punderson State Park
- Boston Mills
- Agora Theatre & Ballroom
- Laurentia Vineyard & Winery
- The Arcade Cleveland
- Cleveland Museum of Art
- Huntington Convention Center of Cleveland
- Edgewater Park Beach
- Debonné Vineyards
- JACK Cleveland Casino
- Cleveland Museum of Natural History
- Stan Hywet Hall and Gardens
- Greater Cleveland Aquarium
- West Side Market
- Edgewater Pier





