
Holiday houses in Streetsboro
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Top-rated holiday rentals in Streetsboro
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Farm Stay in Luxury Barndominium Mantua Ohio
Welcome! Experience our rural farm’s abundance! Take a magical walk through the charming vegetable and flower gardens. Enjoy a beautiful, tranquil stocked fishing pond & Scottish Highlander cattle. If your spirit calls you further take your adventures to the Cuyahoga River, just a stones throw away for kayaking, canoeing, & tubing. After experiencing nature’s gifts outdoors, rest and recharge indoors while connecting to your creative side enjoying the Artist’s inspiration within the loft space.

Luxury Condo in Akron Northside District
Lux. 2 bed/2 bath condo in beautiful Northside district of Akron! Large windows in the living/ bedrooms showing great views of the historic Cuyahoga Valley with easy access to walking/ biking trails. Well appointed space for that family wishing to be close and explore all our beautiful city has to offer or for the business traveler needing a cozy home away for home. Fine dinning, quick bites, and shopping all steps away. Quick highway access to Cleveland or Canton both within a 30 minute drive!

Cozy Apartment in Charming Village
Cozy apartment with private entrance attached to historic house. Central location in this charming tourist village of Chagrin Falls, a short walk to the natural waterfalls, over 20 great restaurants, two ice cream shops & boutique shopping. Low ceilings & compact bathroom, but full kitchen and parking for one car. Non-smokers only. No pets - out of consideration for future guests. Guests must be able to climb stairs to access apartment. Air conditioning is available during the summer season.

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.

Inclusive Breakfast + Coffee from R44 Coffee Shop!
Cozy up with INCLUSIVE coffee + breakfast from R44 Coffee Shop every day of your stay! Step into the comfort of this recently renovated 2BR (*Optional 3rd BR in living room with our sleek Murphy Bed!) 1.5Bath apt in the charming town of Mantua, OH. ✔ 2 Comfortable BRs (*optional 3rd BR in living room with our Murphy Bed!) ✔ Open Design Living ✔ Full Kitchen ✔ Complimentary Breakfast & Coffee ✔ Small Porch ✔ High-Speed Wi-Fi ✔ Smart TV ✔ Washer/Dryer ✔ Free Parking + EV Charging (220 Outlet)

Cedarblock: Modern 3br forest-side escape
Come experience this modern design sanctuary, recently remodeled and surrounded by fairy-tale forest. It's minutes from Highland Square and a quick drive to Cuyahoga National Park, Stan Hywett, Downtown Akron, Blossom Music Center, and more. Less than an hour from Cleveland’s world-class museums, Rock & Roll Hall of Fame, and Lake Erie. Cedarblock provides an inspiring retreat that’s close to convenient amenities but set in a charming and walkable neighborhood, fusing nature, style, and fun.

Cozy Solar Powered Hideaway (Pet Friendly)
Newly built Solar powered 1 BR Private detached garage apartment with loft. This charming pet friendly hideout is situated on a 1.5 acre partially wooded lot. The apartment is equipped with brand new appliances, beautiful wood accents, a cozy loft accessed via ladder, and a wonderful fenced in area for guest dogs! A laundry room is available for guest use in the garage below. Less than 10 min from Chagrin Falls, 30 min to CVNP, 30 min from CLE airport. Convenient keypad entry to apartment.

The Garden Apartment at Heritage Farms
The Garden Apartment (PSTR Permit #2025-20) is a quiet and relaxing home away from home to enjoy after exploring the Cuyahoga Valley National Park. The Garden Apartment features a large bedroom with queen-sized bed, a den with a large sandstone wood-burning fireplace, full kitchen and bathroom with a shower. You'll surely fall in love with this cozy rental! There is a sandstone patio, which offers a shaded sitting area and grill for outdoor cooking, plus a fire ring for evening bonfires.

“Crooked River” House at Hiram
A uniquely beautiful getaway nestled on the bank of The Cuyahoga River. Whether you love nature and the outdoors or just want to relax in “a really cool house”, this place is for you! Everything you need for Hot Tubbing, Kayaking, Canoeing, Relaxing, and River Watching awaits. If outdoors is not your thing, this beautiful home has spectacular River Views and a good mood of its own! The Open Concept features Upscale Modern Design with Nature Safari Vibes and Earthy Cozy Interiors.

Shipping Container Cabin with hot tub!
Enjoy our secluded getaway, that's not too far away! This cabin is made from three combined shipping containers to create one memorable experience for our renters. Housed on ten acres on Beaver creek and surrounded by nature's beauty, this rental is sure to give you the adventure and relaxation you need. Enjoy your favorite drink on one of two beautiful patios, by the fire inside or out, and end your evening in the warmth of our hot tub. Only 6 minutes from Route 11 in Lisbon, OH!

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!

Brandywine Falls Hike, Bike & Relaxation Suite
Private comfortable suite in the beautiful Cuyahoga Valley National Park. Mid-way between Cleve. & Akron. Adjacent to miles of paved walk/bike trails. Bring your bike or use rentals nearby. Visit historic villages of Hudson & Peninsula. Fine dining. Quiet Country estate setting. 5 minute walk to spectacular Brandywine Falls or rest your feet on the ottoman. Spring, Summer and Fall foliage is stunning. Among Ohios most beautiful sight seeing areas.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

NEW! Clean & Private Remodeled Home in Kent

Glamping with Mini Highlander Cows!

Solitude in the Cuyahoga Valley

The JoKo Cottage

Silly Goose At Heron Hill Retreat Hot Tub on Lake!

Crooked River Retreat

Cozy Farmhouse on 13 acres

Quiet and comfortable on 2 acres. Pet friendly!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
- Niagara Falls Holiday rentals
- Indianapolis Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Progressive Field
- Pro Football Hall of Fame
- Rock & Roll Hall of Fame
- Cleveland Browns Stadium
- Headlands Beach State Park
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Boston Mills
- Gervasi Vineyard
- Cleveland Museum of Natural History
- Cleveland Botanical Garden
- Laurentia Vineyard & Winery
- Case Western Reserve University
- Agora Theatre & Ballroom
- Cleveland Museum of Art
- Huntington Convention Center of Cleveland
- Crocker Park
- The Arcade Cleveland
- Debonné Vineyards
- Playhouse Square




