
Holiday rentals 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.

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.

Stylish and comfortable! Close to downtown Akron
Recently renovated, this cozy 2-story colonial offers a full kitchen with gas range, espresso machine, air fryer, dishwasher, and wine fridge. The kitchen side door opens to a fenced-in backyard. The living room has a sofa, large SmartTV and a dining area with seating for 4. The main level bedroom has a twin trundle bed and vanity. Upstairs is a large loft-style bedroom with king-size bed, faux fireplace, work desk, closet and sturdy oak storage furniture. Washer/dryer available in basement.

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.

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.

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!

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

Cuyahoga Country Home
Peninsula OH (Permit # 2026-21) is a friendly village in Summit County with a population of 600. It’s conveniently located close to the Cleveland and Akron Metro areas. Our house is located in the middle of the Cuyahoga Valley National Park which is renowned for cycling and hiking, with countless trails of varying degrees of difficulty. Bicycles can be rented a mere 1/2 mile away. We welcome visitors from all walks of life.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

Fay's House

River House; by River 'n Draft

Heather's Irish Cottage

NEW Peaceful Cottage in Brady Lake

Peaceful 3BR Home • Fully Stocked • Self Check-In

Cozy in Cuyahoga Falls

NEW! Immaculate Lakeside Home in Kent

University of Akron/ Summa Area Attic Apartment
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area 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
- Agora Theatre & Ballroom
- Laurentia Vineyard & Winery
- Case Western Reserve University
- Debonné Vineyards
- Huntington Convention Center of Cleveland
- Cleveland Museum of Art
- The Arcade Cleveland
- Rocky River Reservation
- Playhouse Square




