
Vacation rentals in Streetsboro
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Top-rated vacation 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.

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

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.

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)

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!

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.

The Garden Apartment at Heritage Farms
The Garden Apartment (PSTR Permit #2025-20) is a quiet and relaxing home away from home to enjoy after exploring the Cuyahoga Valley National Park. The Garden Apartment features a large bedroom with queen-sized bed, a den with a large sandstone wood-burning fireplace, full kitchen and bathroom with a shower. You'll surely fall in love with this cozy rental! There is a sandstone patio, which offers a shaded sitting area and grill for outdoor cooking, plus a fire ring for evening bonfires.

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 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.

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

Fay's House

Stay Awhile on Waldo

River House; by River 'n Draft

Bright & Modern Tremont Apartment | Free Parking

West Akron home

Cozy in Cuyahoga Falls

Charming Akron Abode

Balcony Room, Queen + Lots More!
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 vacation rentals in Streetsboro

Total vacation rentals
Explore 20 vacation rentals in Streetsboro

Nightly prices starting at
Streetsboro vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Streetsboro vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- 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
- Pepper Pike Club
- Cleveland Botanical Garden
- Reserve Run Golf Course




