
Holiday houses in Streetsboro
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Top-rated holiday rentals in Streetsboro
Guests agree: these stays are highly rated for location, cleanliness and more.

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 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.

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)

Brupoppy Farm/ A Cozy Retreat Near National Park
Escape to Brupoppy Farm—your private retreat on 8 peaceful acres just minutes from Cuyahoga Valley National Park. Cozy interiors, a welcoming vibe, and plenty of open space make this the perfect getaway for families, couples, and adventures. 25 miles to Cleveland, 15 to Akron and easily accessible to all highways. We have two houses attached into one house. We live in the other house. They each have their own entrance. The focus is on unique amenities & hospitality. Sleep5/6, fee may apply.

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.

“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.

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

Brick Loft in Historic Downtown Canal Fulton
Located in the heart of historic downtown Canal Fulton, this charming brick loft will truly take you back in time. Walk or bike to all the local restaurants and shops around town or grab coffee at The Exchange downstairs. The 13 large windows give a panoramic water view of the canal way and downtown. Every detail in this space has been lovingly created with comfort and inspiration in mind. Relax and enjoy this one of a kind location.

The Triangle: A-Frame Cabin for your city retreat
Cabin retreat in the Village of West Farmington. This 400 sq. ft. A-Frame cabin is perfect for a weekend away from the city to relax, rejuvenate, and rest. The welcoming nature of the cabin is immediately apparent when you walk in - the wood-burning stove, the exposed beams throughout, and the many small details will draw you in to your weekend home. Brand new deck in Fall 2024! Extremely close to The Place at 534.

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.

Cozy cottage close to I-76
Our cozy, farmhouse inspired one bedroom apartment has lots to offer. Constructed from 95% up-cycled materials with amenities that include 1 mile from I-76, NEOMED, Kent State University, Hartville, Portage County Randolph Fairgrounds, CVNP, West Branch State Park, Dusty Armadillo, etc. Designated parking with plenty of room for a trailer.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

Maison Durieux

River House; by River 'n Draft

Cozy guesthouse w/pond overlook

Hudson Hideaway

Cozy spot near downtown C. Falls/national parks

Harmon House

2 Bd Townhome~Walk to Town~CVNP~WRAcademy~Blossom

Clean and Quiet 2 Bedroom Condo Stow
Quick stats about holiday rentals in Streetsboro

Total holiday rentals
Explore 20 holiday rentals in Streetsboro

Nightly prices starting at
Streetsboro holiday rentals start at $105 NZD per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Streetsboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Streetsboro rentals

4.8 Average rating
Streetsboro stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Progressive Field
- Rock and Roll Hall of Fame
- Nelson-Kennedy Ledges State Park
- Pro Football Hall of Fame
- Headlands Beach State Park
- Gervasi Vineyard
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Firestone Country Club
- Cleveland Museum of Natural History
- Guilford Lake State Park
- West Branch State Park
- Boston Mills
- The Quarry Golf Club & Venue
- Lake Milton State Park
- Cleveland Botanical Garden
- Reserve Run Golf Course
- Memphis Kiddie Park
- Brandywine Ski Area
- Pepper Pike Club