
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.

Best Deal in Akron: 1 br Modern Comfort Near CVNP
Please don't let the exterior fool you. Once you enter your private space on the 3rd floor, you'll be pleasantly surprised. Relax in a clean, conveniently located converted 1906 home. 1BR apartment with an open floor plan & furnished with comfort in mind. Close to Route 8 & minutes to downtown Akron and CVNP. Perfect for travel nurses, couples,and nature lovers. Please be aware this is an old attic refurbished,so the ceilings are low. May not be comfortable for anyone over 6 ft NO Cleaning Fee

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

Private upstairs guest suit.
Conveniently located 1 bedroom upstairs guest suite right off I-90. Near the Lorain Antique market strip. 1 minute drive to Gordon Square arts district. 2 minutes to Edgewater beach. A mile to beautiful Ohio city and about 10 minutes to Downtown. Close to Lakewood for all their restaurants and unique shops. This apartment offers all the standard amenities in a colorful old-timey MCM decor to help make you feel right at home. Access through a private back entry via a hassle free electronic lock.

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.

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)

Restored Farmhouse on 88 acre near Cleveland/Akron
Feel refreshed when you stay in this rustic gem. This fully restored 1833 farmhouse incorporates some modern amenities while maintaining the historical look and feel of an early American farmhouse. Explore the nearly 40 acres of private woodlands, or walk around the crop fields on this 88 acre property. Enjoy the use of the large patio and outdoor fireplace. We are a pet friendly property with a $100 pet cleaning charge assessed at the time of booking. A great getaway for guests of all ages!

Clean and Quiet 2 Bedroom Condo Stow
Beautiful two bedroom condo in Stow, Ohio located 3 minutes from route 8. Near Hudson, Kent, Akron, Blossom Music Center, and the Cuyahoga Valley National Park. Local owner! This first floor condo has everything you need to have a comfortable stay. Stocked kitchen, high speed Wifi, and HD smart TV! Private entrance from outside with parking about 15 feet from the entrance. No common hallways; washer and dryer in your unit and plenty of closet space. *We’ve had a long term guest 3 months*

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.

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.

Robin's Nest
Spread out in this spacious ground-floor MIL suite with kitchenette, close to Western Reserve and shopping in charming downtown Hudson. Cuyahoga Valley National Park (Brandywine Falls, Virginia Kendall Ledges) is a quick 15 minute drive. Just minutes from I-80 and I-480. Very quiet residential neighborhood. STR-21-6.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

Fay's House

Tallmage bedroom ,Full size bed

NEW! Immaculate Lakeside Home in Kent

Spacious room, newly renovated with great view

Balcony Room, Queen + Lots More!

Chic & Cozy | Minutes from Downtown & MetroHealth

Cozy Space in a Quaint Place

Large Yard & Fire Pit: Pet-Friendly Ravenna Home!
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
- 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
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- 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
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Boston Mills
- Cleveland Museum of Natural History
- Gervasi Vineyard
- Cleveland Botanical Garden
- Laurentia Vineyard & Winery
- Case Western Reserve University
- Debonné Vineyards
- The Arcade Cleveland
- Agora Theatre & Ballroom
- Playhouse Square
- Rocky River Reservation
- Huntington Convention Center of Cleveland
- Cleveland Museum of Art




