Holiday houses in Streetsboro

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Top-rated holiday rentals in Streetsboro

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Guest favourite
A cozy indoor space features a spacious bed with rustic wooden accents and layered textures. A comfortable sectional sofa is adorned with soft throws and cushions. Natural light filters through large windows, illuminating a decorative console table with sunflowers and various books.
Barn in Mantua
4.95 out of 5 average rating, 104 reviews

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.

Top Guest favourite
Cabin in Middlefield
4.96 out of 5 average rating, 105 reviews

The Wildflower

Come enjoy this brand new cabin in a private wooded setting. Sit on the front porch swing or relax by the fireplace. Enjoy the whirlpool for two and new stylish decor with black metal railing against a backdrop of the finest craftsmenship of woodworking. This cabin was built by local Amish and Mennonite builders. There is a double reclining loveseat and a queen size pull out sofa with a memory foam mattress. We provide snacks, sodas, coffee, tea, cereal, juice, pancaKe mix & maple syrup!

Guest favourite
A secluded Safari tent is situated among trees, illuminated by string lights. A gravel area features several dark wooden Adirondack chairs arranged around a fire pit, inviting relaxation in the serene outdoor setting.
Place to stay in Wooster
4.98 out of 5 average rating, 132 reviews

Luxury Creekside Safari Tent w/ King Bed *Hot Tub*

Escape to a secluded luxury Safari tent situated on 60 wooded acres that overlooks Little Killbuck Creek. Enjoy hiking trails & a natural waterfall a short hike upstream. The tent is built on a platform deck with canvas sides, metal roof, high end luxury flooring, luxurious King size bed, full kitchen, dining, A/C, ceiling fans & heaters. The large separate bath house boasts a rainfall shower and bluetooth speakers. Enjoy a hot tub that overlooks the creek & front porch for bird watching.

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, 141 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.

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.

Guest favourite
A comfortable living area features a spacious sofa and a leather chair beside a coffee table. Large windows allow natural light to enter, framed by patterned curtains. A flat-screen TV is mounted on a light wood console, and a potted plant adds a touch of greenery.
Home in Hiram
4.96 out of 5 average rating, 145 reviews

“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.

Top Guest favourite
The exterior of Apple Blossom Cottage is showcased with a modern white facade and a distinctive metal roof. A welcoming porch features rocking chairs and a scenic view of the rolling hills in the background. The landscape includes well-maintained greenery and a gravel pathway.
Cottage in Millersburg
4.99 out of 5 average rating, 244 reviews

Apple Blossom by Olde Orchard Cottages

Welcome to Apple Blossom Cottage... We invite you to be our guest! For years Mary + John, the founders of White Cottage Company, dreamed of creating a space for people to retreat to that would be so cozy, peaceful, and relaxing that guests wouldn't want to leave! Their dream is now a reality with the completion of Olde Orchard Cottages Apple Blossom + Sparrow's Nest - nestled within the serene rolling hills in the heart of beautiful Amish Country.

Top Guest favourite
A welcoming entrance features a vibrant yellow door surrounded by decorative garlands and twinkling lights. A white wreath adorns the door, while a festive snowman stands on the stone steps, complemented by a red scarf. A snowflake decorates the adjacent wall.
Guesthouse in Chardon
5 out of 5 average rating, 157 reviews

Private, Quiet 1 BR 1 Bath Chardon Guesthouse

Enjoy a respite at this peaceful and centrally-located, newly renovated guesthouse. Large 1BR w full bath. Sleep with the windows open - it's that quiet. Living room and full, eat-in kitchen. Private patio for outdoor dining. Walk to historic Chardon Square and enjoy its many festivals & activities. Easy drive to Amish country, wineries, Lake Erie and its coastal towns and beaches, The Great Geauga County Fair, 40 minutes to downtown Cleveland.

Guest favourite
A bright bedroom features a spacious bed with plaid bedding and decorative yellow pillows. Two bedside tables hold matching lamps, providing soft illumination. Natural light filters through horizontal blinds, creating a warm atmosphere. A framed artwork is displayed above the headboard, complementing the serene décor.
Apartment in Ravenna
4.96 out of 5 average rating, 183 reviews

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

Top Guest favourite
The exterior of a cottage features a welcoming entrance with a wooden deck, adorned with potted flowers. A bench provides a seating area, while greenery enhances the landscape. The cottage's siding showcases a neutral tone, and a gabled roof adds architectural interest.
Guesthouse in Middlefield
4.97 out of 5 average rating, 165 reviews

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.

Top Guest favourite
The living area features comfortable seating with a plush sofa and a leather armchair. Natural light filters through the windows, illuminating an inviting atmosphere. A small table with chairs is visible, along with a decorative rug enhancing the space's warmth.
Home in Peninsula
4.99 out of 5 average rating, 250 reviews

Cuyahoga Country Home

Peninsula OH (Permit # 2026-21) is a friendly village in Summit County with a population of 600. It’s conveniently located close to the Cleveland and Akron Metro areas. Our house is located in the middle of the Cuyahoga Valley National Park which is renowned for cycling and hiking, with countless trails of varying degrees of difficulty. Bicycles can be rented a mere 1/2 mile away. We welcome visitors from all walks of life.

Top Guest favourite
The spacious studio features original exposed brick walls and high ceilings with rustic wooden beams. Large windows allow natural light to illuminate the area. A dining table is centered, surrounded by comfortable seating, and a wall adorned with historical remnants is visible in the background.
Loft in Minerva
4.99 out of 5 average rating, 474 reviews

Luxury Brewery Loft | Steps to Taproom | King Bed

Nestled in downtown Minerva just two doors from Sandy Springs Brewing Co., The BQ is a luxury historic 1800s second-floor studio. Original brick walls, exposed beams, warm finishes, a copper kitchen sink, and a digital rain shower with body jets create a cozy yet elevated stay. Enjoy a king bed, leather chesterfield chair, and sleeper sofa. Walk to the brewery. Check-in beers included.

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