
Holiday houses 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

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.

“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.

Entire Home Highland Square/CVNP
Enjoy a comfortable experience at this centrally-located home 1 block away from the strip in Highland Square. Central air, 2 bedrooms with brand new queen beds. Large kitchen with dishwasher. Netflix & Prime Video on tv's. Comfortable leather couches, front and back deck, and fire pit. Being 5 minutes from Downtown Akron, 35 minutes from Downtown Cleveland, and 10 minutes from Cuyahoga Valley National Park, there is a lot of nightlife, hiking and biking in the area. All are welcome!

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

Relaxing Retreat Near Blossom & CVNP
Escape to our beautifully updated 2-bedroom home in picturesque Hudson, Ohio, just minutes away from the stunning Cuyahoga Valley National Park, Blossom Music Center, and Boston Mills Ski Resort. Our location is also conveniently close to Western Reserve Academy and excellent local restaurants, making it the perfect retreat for families or groups of friends.

Pav's Place 1BD/1BA Private w/Queen Bed!
Welcome to your home away from home in Akron! This renovated duplex was built in 1919 and is located in a safe & calm residential neighborhood. Easy access to downtown, exploring Cuyahoga National Park or seeing a show at Blossom. Student or traveling medical professional? Akron University, Cleveland Clinic and Summa Health are all within a 5min drive.
Tremont • urban cottage
-Cottage size / urban vibe- Private, Secure & Convenient location w/ off street parking! block steam shower w/heated towel bar. polished concrete floors/Italian pro kitchenette /washer dryer combo. Check out our other Airbnb listing right next door! Tremont • urban flat https://www.airbnb.com/rooms/45341618?viralityEntryPoint=1&s=76
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

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

Studio apartment near Cuyahoga National Park

Cozy guesthouse w/pond overlook

Hudson Hideaway

Crooked River Retreat

Best Deal in Akron: 1 br Modern Comfort Near CVNP

Clean and Quiet 2 Bedroom Condo Stow

Restored Farmhouse near Cleveland/Akron
Frequently Asked Questions
Are there family-friendly vacation rentals in Streetsboro?
Streetsboro has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Streetsboro?
Yes! Work meets play with ease at over 10 vacation rentals in Streetsboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
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
- Indianapolis Holiday rentals
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- Detroit Holiday rentals
- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Cleveland Browns Stadium
- Rock & Roll Hall of Fame
- Progressive Field
- Pro Football Hall of Fame
- Headlands Beach State Park
- Little Italy
- Mosquito Lake State Park
- 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
- The Arcade Cleveland
- Playhouse Square
- Cleveland Museum of Art
- Huntington Convention Center of Cleveland
- Edgewater Park Beach




