
Holiday houses in Streetsboro
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Top-rated holiday rentals in Streetsboro
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Hudson Hideaway
Welcome to our cozy suite in charming Hudson, OH – an idyllic retreat perfect for couples or solo travelers looking for a private, peaceful escape. This intimate space combines comfort, style and relaxation with touches of luxury to make your stay unforgettable. Private patio and screened porch/entryway, two-person infrared sauna, fireplace, two Roku TVs and fully equipped kitchen with complimentary coffee bar. Minutes from downtown Hudson, Cuyahoga Valley National Park and Blossom Music Center.

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.

Cozy guesthouse w/pond overlook
Experience this peaceful and centrally-located 2-bedroom, 1-bath space. Close to shopping and highways, yet with an out-in-the-country feel. Roam our 4.5 private acres, fish in the stocked pond, or relax by the fire pit. Owners live on-site with 2 friendly dogs who’d love to say hello. Nearby attractions include CV National parks, Blossom Music Center, downtown Cleveland, and Boulder Creek—an award-winning golf course just minutes away. Wineries, bike trails, and canoe adventures await as well.

“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.

White Pond Drive get away
Home Away at White Pond Drive Contemporary decore in this clean 900 Square foot ranch. Home all to yourself. Large, new kitchen, full bathroom, sunroom, internet, basic cable & DVD (TV in LR & MBR) treadmill, W&D in basement. Train tracks across the street, so you will hear the train rumble by and the horn. West Akron less than a mile from restaurants, close to expressway. Nestled between Highland square, Fairlawn, and Copley. Great location. Pet friendly for one pet only please!

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.

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

The School House Streetsboro
This special place is close to everything, making it easy to plan your visit. The school house is one of streetsboro first one room school houses it has been remodeled as stand alone house. Conveniently located in down town Streetsboro, minutes from almost every store and restaurant, and close to the turnpike and 480. It sits on a secluded, tree lined acre lot.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

NEW! Clean & Private Remodeled Home in Kent

Studio apartment near Cuyahoga National Park

Harmon House

Crooked River Retreat

Short walk to river or downtown

Woodside Estate

Best Deal in Akron: 1 br Modern Comfort Near CVNP

Clean and Comfortable 2 Bedroom Condo in Stow
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
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- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
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- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Cleveland Browns Stadium
- Progressive Field
- Rock & Roll Hall of Fame
- Pro Football Hall of Fame
- Headlands Beach State Park
- Mosquito Lake State Park
- Little Italy
- Cleveland Metroparks Zoo
- Punderson State Park
- Boston Mills
- Cleveland Museum of Natural History
- Gervasi Vineyard
- Cleveland Botanical Garden
- Laurentia Vineyard & Winery
- Agora Theatre & Ballroom
- Case Western Reserve University
- Cleveland Museum of Art
- Huntington Convention Center of Cleveland
- Debonné Vineyards
- Playhouse Square
- The Arcade Cleveland
- Rocky River Reservation




