Holiday houses in Streetsboro

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Top-rated holiday rentals in Streetsboro

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Guest favourite
The living room showcases a modern design with wood paneling and comfortable seating. A bar cart is visible, ready for refreshments. The bedroom features a geometric accent wall behind a queen bed with coordinated pillows, promoting a balanced aesthetic.
Townhouse in Hudson
4.98 out of 5 average rating, 100 reviews

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

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, 101 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
A cozy bedroom features a queen-size bed with a light green coverlet. Decorative floral prints adorn the walls. A bedside lamp and a wooden nightstand are positioned nearby. A sliding mirrored closet door reflects the space, adding depth to the inviting atmosphere.
Apartment in Chagrin Falls
4.97 out of 5 average rating, 600 reviews

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.

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, 474 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
A warm entryway is presented with a dark accent wall. A wooden bench is paired with hooks for coats and bags, creating an inviting first impression. Storage cabinets are neatly arranged on one side, complemented by greenery in a vase.
Apartment in Mantua
5 out of 5 average rating, 108 reviews

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)

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, 224 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 bedroom features a large bed with a gray blanket and decorative pillows. Two windows with gray curtains allow natural light to enter. A wooden dresser and a small workspace with a chair are also present, enhancing the room's functionality.
Home in Kent
4.94 out of 5 average rating, 157 reviews

Bright Kent Retreat | Walk to Downtown & KSU

🛏 3 bedrooms • 1.5 bathrooms • Sleeps 6 ☕ Bright sunroom • Dedicated workspace 🍳 Updated kitchen • Fully stocked for home cooking 🚶 Walk to downtown Kent’s shops, cafés & restaurants, and KSU! 🐾 Pet-friendly • Free off-street parking for 2 cars (3 cars should fit but can be tight) 💻 Ideal for families, remote work, or university visits Find comfort and charm in this spacious Kent retreat—perfectly located just minutes from downtown and Kent State University.

Top 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
4.97 out of 5 average rating, 179 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
An open living area features a comfortable sofa and an accent chair, set against a backdrop of vaulted ceilings. Natural light enters through several windows, illuminating the space. A fireplace and a view into the kitchen area can also be seen.
Home in North Hill
4.92 out of 5 average rating, 287 reviews

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.

Superhost
The A-Frame cabin stands among towering trees, showcasing its distinct triangular shape and large front deck. Surrounded by lush greenery, the wooden façade and black accents blend harmoniously with the natural environment, creating a sense of privacy and seclusion.
Cabin in West Farmington
4.9 out of 5 average rating, 728 reviews

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.

Guest favourite
The living area features a light-filled space with a cozy sectional sofa and a wooden coffee table. A flat-screen TV stands on a console against the wall, while a dining area is set with a round table and elegant chairs. Sliding glass doors lead to the outside.
Apartment in Hudson
4.92 out of 5 average rating, 180 reviews

Relaxing Retreat Near Blossom & CVNP

Escape to our beautifully updated 2-bedroom home in picturesque Hudson, Ohio, just minutes away from the stunning Cuyahoga Valley National Park, Blossom Music Center, and Boston Mills Ski Resort. Our location is also conveniently close to Western Reserve Academy and excellent local restaurants, making it the perfect retreat for families or groups of friends.

Guest favourite
An inviting covered outdoor sitting area is enhanced by string lights overhead, creating a cozy atmosphere. Two wooden chairs are positioned beside a small table on a textured rug, with a decorative window in the background adding charm to the space.
Guesthouse in Rootstown
4.88 out of 5 average rating, 177 reviews

Cozy cottage close to I-76

Our cozy, farmhouse inspired one bedroom apartment has lots to offer. Constructed from 95% up-cycled materials with amenities that include 1 mile from I-76, NEOMED, Kent State University, Hartville, Portage County Randolph Fairgrounds, CVNP, West Branch State Park, Dusty Armadillo, etc. Designated parking with plenty of room for a trailer.

Popular amenities for Streetsboro holiday rentals

Frequently Asked Questions

  • 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.

  • Are there pet-friendly vacation rentals in Streetsboro?

    Four-legged friends are welcome in Streetsboro. Choose from more than 10 vacation rentals for guests traveling with pets.

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 $92 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!

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