Holiday houses in Streetsboro

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Top-rated holiday rentals in Streetsboro

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Top Guest favourite
Cabin in Madison
4.96 out of 5 average rating, 238 reviews

LemonDrop Lake-Front Cottage

Fully remodeled in 2024, LemonDrop Cottage is a Lake-Front property, with direct access by stairwell down to a small private beach directly on Lake Erie. Lake is viewable from the Kitchen or Bedroom windows. All New Windows, Hickory hardwood floors, shower, electric flat-top oven, retro-Fridge, retro-Microwave/Toaster, Keurig, King-size mattress, Twin sofa-bed, BBQ grill (propane provided), and fire pit with wood provided. Cottage built in 1949 as a fishing cottage, adorable Lake-Front Cabin wit

Top Guest favourite
The exterior of a modern ranch house is showcased, featuring a vibrant red façade and a metal roof. A spacious deck is visible, complete with outdoor seating and a view of the nearby creek and surrounding trees. A gravel driveway leads to the entrance.
Home in Garrettsville
4.99 out of 5 average rating, 511 reviews

“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.

Top Guest favourite
An aerial view of a historic home surrounded by vibrant fall foliage, showcasing a mix of oranges, yellows, and greens. The property is set against a backdrop of trees, with a clear view of the main road in front. The home's charming exterior complements the natural landscape.
Home in Peninsula
4.97 out of 5 average rating, 115 reviews

Hot Tub, CVNP, Private Waterfall Trail, Firepit

Welcome to River Rock Retreat, a haven in the heart of Cuyahoga Valley National Park. Enjoy the hot tub with a nature view and explore the private trail leading to a stunning waterfall. Unwind by the outdoor fire pit, surrounded by bistro lights, and savor a barbecue with the gas grill. Walk to downtown Peninsula's coffee shop, dining, and shops, or trails in CVNP and the Cuyahoga Valley Scenic Railroad. A short drive brings you to Brandywine/Boston Mills Ski Resorts and Blossom Music Center.

Top Guest favourite
The cottage is set amidst tall trees, showcasing a serene front porch that invites relaxation. Lush green grass surrounds the home, complemented by a decorative birdbath in the foreground. The exterior features a mix of green siding and white trim, harmonizing with the natural surroundings.
Home in Cuyahoga Falls
4.98 out of 5 average rating, 142 reviews

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.

Top Guest favourite
A spacious living area features a leather sofa paired with two green armchairs, arranged around a wooden coffee table. Large windows provide views of the forest, while a dining table for six is situated in the background beneath a light fixture.
Chalet in Middleburg Heights
4.96 out of 5 average rating, 108 reviews

Groovy Cedar Chalet Forest View

Our retro inspired chalet offers a secluded forest setting with excellent access to convenient amenities! Our family-friendly space comfortably sleeps 6 guests. Each room has been thoughtfully appointed for your convenience and authentic aesthetic. The entire home is yours to use. The fully equipped kitchen and laundry room are a great bonus. On Sunny and rainy days alike- sip a fresh cup of coffee on the spacious front porch. An attached 3 car garage and driveway allows for ample parking.

Guest favourite
An open-concept living space features a modern kitchen with stainless steel appliances and a spacious wooden countertop. Black bar stools sit against the island, and a comfortable gray couch with a throw blanket is positioned nearby. A ladder leads to the loft area, with a door leading to the bedroom visible in the background.
Apartment in Chagrin Falls
4.87 out of 5 average rating, 233 reviews

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.

Top Guest favourite
A spacious backyard is highlighted by a large, weeping willow tree providing shade over a grass area. Outdoor seating with lounge chairs is positioned facing Lake Erie, offering a view of the water. A peaceful atmosphere is accentuated by a small decorative planter in the foreground.
Cottage in Willoughby
4.99 out of 5 average rating, 206 reviews

Lydia's Lake Erie Cottage

In the heart of Willoughby, a cozy cottage awaits you as the perfect getaway spot. Situated on the shores of Lake Erie, you'll be able to enjoy stunning lake views on the water's edge. Inside, you'll find a cozy and well-appointed space, complete with a fully stocked kitchen and outdoor grill, Unwind by the fireplace in the living room or catch up on your favorite shows on the smart TV. Stay connected with the free WiFi, and take advantage of the laundry with a washing machine and dryer.

Top Guest favourite
The living area is furnished with comfortable leather couches and a wooden coffee table, creating a relaxing space. A large television displays streaming options, while natural light enters through the windows, highlighting decorative plants and wall art.
Home in Highland Square
4.95 out of 5 average rating, 159 reviews

Entire Home Highland Square/CVNP

Enjoy a comfortable experience at this centrally-located home 1 block away from the strip in Highland Square. Central air, 2 bedrooms with brand new queen beds. Large kitchen with dishwasher. Netflix & Prime Video on tv's. Comfortable leather couches, front and back deck, and fire pit. Being 5 minutes from Downtown Akron, 35 minutes from Downtown Cleveland, and 10 minutes from Cuyahoga Valley National Park, there is a lot of nightlife, hiking and biking in the area. All are welcome!

Top Guest favourite
A rustic cabin, made of cedar, is nestled in the woods. The structure features a wrap-around deck and is surrounded by a serene pond and vibrant greenery. Purple flowers in the foreground enhance the natural setting, providing a peaceful atmosphere.
Cabin in Burton
4.93 out of 5 average rating, 185 reviews

Ma & Pa’s Romantic Cabin Fireplace Outdoor Bath

Nestled in the Woods of Geauga County is the home of Ma & Pa’s Cabin. A Getaway perfect for the weary traveler or great vacation spot! Surrounded by mature woods. Ma & Pa’s offers a unique adventure but just like home experience. Private, Hiking/Biking Trail, Fireplace, Outdoor Wood Fire pit, Spacious Kitchen, Outdoor Bath (No Jets) including Wifi. Golfing, Skydiving, Cuyahoga Valley National Park, Nelson Ledges State Park, Amish Region. Adventure Awaits at Ma & Pa’s Cabin!

Top Guest favourite
A cozy living area features a comfortable gray sofa adorned with decorative cushions. A coffee table rests in front, and a television stands on a wooden stand. A brick fireplace serves as a focal point, surrounded by a subtle color palette and artwork.
Home in Mogadore
4.98 out of 5 average rating, 151 reviews

Amaryllis 3 BDR House Country Quiet near Kent OH

Amaryllis Guest House - a slice of country charm with lovely peaceful surroundings. Quiet, secluded home with country views and dark skies - great for birdwatching, golfing, hiking, relaxing. Guests from all walks of life are welcome, but absolutely no parties or events are allowed. Convenient for Kent (15 min), NEOMED (5 min), and Akron. Close to Dusty Armadillo, wineries, golfing, and hiking trails. Country peace and quiet but close enough to town for fine dining.

Top Guest favourite
An open-concept living area features exposed brick walls and high ceilings with dark beams. A large island sits in the kitchen, while comfortable seating is arranged nearby. Multiple windows provide natural light and a view of the surroundings, enhancing the spacious feel of the loft.
Loft in Canal Fulton
4.99 out of 5 average rating, 373 reviews

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.

Guest favourite
Home in Akron
4.83 out of 5 average rating, 202 reviews

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.

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