
Holiday rentals in Streetsboro
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Top-rated holiday rentals in Streetsboro
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2 Bd Townhome~Walk to Town~CVNP~WRAcademy~Blossom
You'll be perfectly located within walking distance to downtown & WRA. Convenient for exploring the area's major attractions. Whether you're seeking outdoor adventures or cultural experiences, our townhome is the perfect base for your exploration of Hudson's captivating attractions. - .5 miles to Downtown Hudson - 1.3 miles to Western Reserve Academy - 5 miles to Cuyahoga Valley National Park - 20 minutes to Blossom Music Center - 25 minutes to Stan Hywet Hall - Keyless entry - Wifi - Patio

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.

Fenced Yard + BBQ | Smart TV | Stocked Kitchen
Pet-friendly, solar-powered private home with a fully stocked kitchen, washer/dryer, fenced yard, coffee bar, and room for 10 guests. + 1,800 ft² house + 1/4 acre fully fenced yard for small and large pets + 43" Smart TV with Disney+ and other apps + 30Mbps WiFi + Fully stocked kitchen with essentials, coffee, and quality cookware + Parking for 5+ cars + Quiet neighborhood + Centrally located between Akron and Canton ★★★★★"Christa’s place was more than what we could have asked for! 10/10!!!”

“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.

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)

Cozy Cottage in Woods/Cuyahoga Valley NP, Blossom
Kick back and relax in this peaceful cottage in the woods! So quiet and private but very close to CVNP, Blossom Music Center, restaurants, shopping, Stan Hywet Hall, Weathervane Theater, and much more! Centrally located between Akron and Cleveland. Mountain Bike trails are just 1/2 mile away. Front and back porches to enjoy nature, tall trees, and ravines. Fully-equipped kitchen, gas fireplace. First-floor queen bed, two comfy twin beds in upstairs bedroom, and loft for reading or work.

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.

Ma & Pa’s Romantic Cabin Fireplace 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!

Bright Kent Retreat | Walk to Downtown & KSU
🛏 3 bedrooms • 1.5 bathrooms • Sleeps 6 ☕ Bright sunroom • Dedicated workspace 🍳 Updated kitchen • Fully stocked for home cooking 🚶 Walk to downtown Kent’s shops, cafés & restaurants, and KSU! 🐾 Pet-friendly • Free off-street parking for 2 cars (3 cars should fit but can be tight) 💻 Ideal for families, remote work, or university visits Find comfort and charm in this spacious Kent retreat—perfectly located just minutes from downtown and Kent State University.

Brupoppy Farm A Cozy Farmhouse Near National Park
Escape to Brupoppy Farm, a private retreat set on 8 peaceful acres & minutes from Cuyahoga Valley National Park. The home blends cozy, refined interiors with open green space—ideal for families, couples, and outdoor enthusiasts. Located 25 miles from Cleveland and 15 miles from Akron, The home consists of 2 attached residences, each with its own private entrance. We reside in the adjoining home and are available as needed, while always respecting guest privacy.

Treetop views in Kent
Located 2 miles from Kent State University and 3 miles from NEOMED . This is a safe quiet country apartment suitable for a quick getaway or a professional longer term work stay. Private, clean, and organized. BIG space and full modern kitchen. Secure and quiet. Simple, cozy, comfortable, and all yours - skip the hotel room and feel at home. Cook and eat healthy! STAY SMALL/STAY SAFE. ENHANCED cleaning per CDC. NO SMOKING OR VAPING ALLOWED

Unique Farm Stay -Brandywine Falls -Peaceful CVNP
Unique guest house located on an authentic farmstead. Property borders the Cuyahoga Valley National Park where countless adventures await. Walk to Brandywine Falls, the park's crown jewel, from the farm. It is a 10 minute walk. Nearby attractions include the historic areas of Hudson and Peninsula, and Stan Hywet Hall & Gardens. Bucolic Amish country less than an hour drive. Cleveland and Akron city centers are not too far.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

The Octagon at Deerfield

Pvt. Cabin 30Ac. Horses, Pool, River & Trails

Christmas Cabin at the Rootstown Reindeer Farm

Solitude in the Cuyahoga Valley

Cottage on the lake

The Gathering Place

The Cottage at Bath Hollow Farm | Visit CVNP

Charming 2 BR 20 m. from Boston Mills & Blossom
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
- Niagara Falls Holiday rentals
- Indianapolis Holiday rentals
- Pittsburgh Holiday rentals
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- 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
- Agora Theatre & Ballroom
- Case Western Reserve University
- Cleveland Museum of Art
- The Arcade Cleveland
- Huntington Convention Center of Cleveland
- Debonné Vineyards
- Rocky River Reservation
- Geneva State Park




