
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.

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.

Gorgeous Farm Stay In HEART of Northeastern Ohio
We have a lovely 2 bedroom, FIRST FLOOR guesthouse on our FAMILY farm with lush gardens and farm animals. ASK for farm tour on the gator from Eric! Cozy space with garden views, eat-in kitchen, full bath, comfy twin bed, queen bed, & pull out living room couch. We include all your soaps, shampoo, and linens. In Summer, feel free to pick a few veggies for your dinner from our large gardens! Grab a bouquet of flowers, too! Friendly, well-behaved PETS WELCOME w/ fee. Ask Me for long-term rates!

“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)

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.

Cabin in the Woods
Our cozy cabin is located near Lake Rockwell with lots of trees and outside space. The inside of our home has 4 skylights that welcome lots of natural sunshine. There is a sauna in the basement and a wonderful park called Towner's Woods located just a mile and a half away. We are also 10 minutes from Kent State University and downtown Kent. We recommend having a an all wheel or 4 wheel drive car for winter. If there’s a lot of snow and you don’t, you could get stuck!

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

Entire home 10 minutes from Cuyahoga National Park
Enjoy a stylish and peaceful experience at this centrally-located bungalow. Summit house is conveniently located 7 minutes to University of Akron and all of the hospitals. Centrally located, Summit House offers easy access to Cuyahoga Valley National Park, Stan Hywet Hall, Brandywine and Boston Mills Ski Resort, Blossom Music Center, Akron Zoo, Akron Art Museum, local metro parks and a range of exciting attractions.

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.
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

River House; by River 'n Draft

Cozy guesthouse w/pond overlook

Hudson Hideaway

Cozy spot near downtown C. Falls/national parks

Harmon House

Suite

Clean and Quiet 2 Bedroom Condo Stow

Downtown Kent NY Style Penthouse
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.
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 $104 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!
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- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Progressive Field
- Rock & Roll Hall of Fame
- Pro Football Hall of Fame
- Nelson-Kennedy Ledges State Park
- The Arcade Cleveland
- Headlands Beach State Park
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Firestone Country Club
- Cleveland Museum of Natural History
- Boston Mills
- Guilford Lake State Park
- West Branch State Park
- Lake Milton State Park
- The Quarry Golf Club & Venue
- Brandywine Ski Area
- Memphis Kiddie Park
- Pepper Pike Club
- Cleveland Botanical Garden
- Reserve Run Golf Course




