
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.

Cozy + Bright Lakeshore Cottage
Relax in this sunny cottage steps away from the Lake Erie shore. Comfy living room opens to the dining room (or home office - you choose!) Kitchen is well stocked and ready for the chef. Main bedroom and full bath are loft-style on the second level. Additional smaller bedroom and half bath on the first floor. Washer/dryer in the basement. Private driveway. Friendly and authentic Cleveland neighborhood. Terrific natural sunlight will brighten your stay and make THIS your Cleveland *happy place!*

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.

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

Spacious 2 Bedroom House
Spacious two bedroom house in a quiet neighborhood away from city noise and only 7 minutes away from Downtown Akron where many go for dining and experiences. There is plenty of parking in the driveway. We offer many amenities and the property is fully secured. Beautiful, tranquil fish pond outside to admire on warm summer days in Ohio. There will be someone available at all times to assist you if you should need anything.

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

Vintage apartment

River House; by River 'n Draft

Cozy guesthouse w/pond overlook

Hudson Hideaway

Harmon House

Cozy cottage close to I-76

Cozy Country Retreat

Woodside Estate
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 $91 AUD 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
- Pro Football Hall of Fame
- Nelson-Kennedy Ledges State Park
- Headlands Beach State Park
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Cleveland Museum of Natural History
- Firestone Country Club
- Boston Mills
- Guilford Lake State Park
- West Branch State Park
- Lake Milton State Park
- The Quarry Golf Club & Venue
- Memphis Kiddie Park
- Brandywine Ski Area
- Cleveland Botanical Garden
- Reserve Run Golf Course
- Pepper Pike Club
- Funtimes Fun Park




