
Holiday houses in Streetsboro
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Top-rated holiday rentals in Streetsboro
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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

Luxury Condo in Akron Northside District
Lux. 2 bed/2 bath condo in beautiful Northside district of Akron! Large windows in the living/ bedrooms showing great views of the historic Cuyahoga Valley with easy access to walking/ biking trails. Well appointed space for that family wishing to be close and explore all our beautiful city has to offer or for the business traveler needing a cozy home away for home. Fine dinning, quick bites, and shopping all steps away. Quick highway access to Cleveland or Canton both within a 30 minute drive!

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)

Cozy Cottage in Woods/Cuyahoga Valley NP, Blossom
Kick back and relax in this peaceful cottage in the woods! So quiet and private but very close to CVNP, Blossom Music Center, restaurants, shopping, Stan Hywet Hall, Weathervane Theater, and much more! Centrally located between Akron and Cleveland. Mountain Bike trails are just 1/2 mile away. Front and back porches to enjoy nature, tall trees, and ravines. Fully-equipped kitchen, gas fireplace. First-floor queen bed, two comfy twin beds in upstairs bedroom, and loft for reading or work.

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.

Brupoppy Farm A Cozy Farmhouse Near National Park
Escape to Brupoppy Farm, a private retreat set on 8 peaceful acres & minutes from Cuyahoga Valley National Park. The home blends cozy, refined interiors with open green space—ideal for families, couples, and outdoor enthusiasts. Located 25 miles from Cleveland and 15 miles from Akron, The home consists of 2 attached residences, each with its own private entrance. We reside in the adjoining home and are available as needed, while always respecting guest privacy.

Little House on the Farm
The accommodation is a 2 bedroom cottage on our small farm that has been recently renovated. It is wheel chair accessible. We are in the middle of the fourth largest Amish community in the world. We are half a mile from the center of Mesopotamia, which is known for the End of the Commons General Store and the annual OX roast over the 4th of July. Cleveland and Youngstown are both approximately 45 minutes away. Lake Erie is 30 minutes north.

Davis Ranch 5 Bedrooms Sleeps 10 & 3 1/2 baths
Overlooking Davis Lake, beautiful sunrises & 8 Acres. Will rent to 2 - 10 people on any given night. Guests will have the entire home as Host does not book more than one guest. No 1 Night stays please. Children under 2 there is no charge. Dogs no charge. I believe in making your stay a very memorable occasion. Please read the reviews that really tell the Ranch Story. In this Century Home you will have Three Full Baths and One 1/2 bath.

Downtown Brick Loft Above The Exchange Coffee Co
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.

Unique Farm Stay -Brandywine Falls -Peaceful CVNP
Unique guest house located on an authentic farmstead. Property borders the Cuyahoga Valley National Park where countless adventures await. Walk to Brandywine Falls, the park's crown jewel, from the farm. It is a 10 minute walk. Nearby attractions include the historic areas of Hudson and Peninsula, and Stan Hywet Hall & Gardens. Bucolic Amish country less than an hour drive. Cleveland and Akron city centers are not too far.

The Cottage at FarmFlanagan
We are a cottage like residence in one of the few small towns between the cities of Cleveland and Akron, Ohio; right down the road from Michael Angelo's Winery and not far from the beautiful Cuyahoga Valley National Park, Boston Mills + Brandywine Ski Resorts, and under an hour to the Pro Football Hall of Fame. The cottage is tucked a driveway away from our old farm house and century old barn. Enjoy this relaxing getaway!
Popular amenities for Streetsboro holiday rentals
Other great holiday rentals in Streetsboro

Christmas Cabin at the Rootstown Reindeer Farm

Amaryllis 3 BDR House Country Quiet near Kent OH

Cozy guesthouse w/pond overlook

Hudson Hideaway

Hop House - Historic home, Kent

Short walk to river or downtown

Restored Farmhouse near Cleveland/Akron

Quaint + Modern - Walkable to town/WRA!
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
- Progressive Field
- Rock & Roll Hall of Fame
- Pro Football Hall of Fame
- Cleveland Browns Stadium
- 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
- Agora Theatre & Ballroom
- Case Western Reserve University
- The Arcade Cleveland
- Huntington Convention Center of Cleveland
- Cleveland Museum of Art
- Rocky River Reservation
- Debonné Vineyards
- Geneva State Park




