Holiday rentals in Oakwood Village

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Top-rated holiday rentals in Oakwood Village

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Guest favourite

Guest house in University Heights

4.98 out of 5 average rating, 228 reviews

Tyndall Carriage House-Private Guesthouse

Price includes cleaning and occupancy fees. Tyndall Carriage House is a quiet and private guesthouse, located in a detached unit behind our home, above the garages. Perfect for a weekend getaway or longer stays. The neighborhood is walk/bike-able, close to John Carroll University, Cedar-Lee District, Fairmount Circle, and Van Aken District with many fun shops and exciting restaurants nearby. A fifteen minute drive takes you to downtown Cleveland, The Cleveland Clinic and other city attractions.

Guest favourite

Guest house in Chardon

4.94 out of 5 average rating, 162 reviews

Chardon Loft

Large private studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels are provided. The furnace is nontraditional. It is open and not in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Guest favourite

Flat in Chagrin Falls

4.97 out of 5 average rating, 501 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.

Guest favourite

Home in Garrettsville

5.0 out of 5 average rating, 312 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.

Guest favourite

Cabin in Solon

4.84 out of 5 average rating, 137 reviews

Cabin in the woods

We have a 900 sq.ft. , log cabin in the woods. The woods of Solon, OH. A southeast suburb of Cleveland. The cabin has 2 bedrooms, each with a queen bed and lots of built in cabinets. They share full bath. As you enter the mud room, to the right is a laundry room with washer & dryer, straight ahead the great room complete with a stone fireplace lots of windows and a small functional kitchen. Welcome to your home in the woods!! We have installed a brand new furnace, keeping the cabin toasty

Guest favourite

Flat in Chagrin Falls

4.87 out of 5 average rating, 171 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

Farm stay in Peninsula

4.97 out of 5 average rating, 115 reviews

The Garden Apartment at Heritage Farms

The Garden Apartment (PSTR Permit #2024-20) 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.

Guest favourite

Home in Parma

4.99 out of 5 average rating, 157 reviews

"Arranged for Two" Read my reviews!

"Arranged for Two", Kelly’s Kempt Corner-remodeled PRIVATE home: living room, kitchen, study, bedroom on first floor, and bonus room. Perfect for couples seeking a KING size bed or fantastic for professionals traveling! Military and Public Service friendly. The king size bed is completely incased and layered: Calvin Klein pillows, 100% polyester microfiber sheets, and comforter duvet, and a smooth, luxury satin quilt. Clean and comfortable! Parties or gatherings will not be permitted!

Guest favourite

Cabin in Euclid

4.92 out of 5 average rating, 194 reviews

Century-plus Summer Cabin - The Perfect Getaway!

Cabin.141 is a 120 year old summer cabin that has been added on to & modified more than a few times over the years! Situated in the inner-ring suburb of Euclid, this charming property is just a few houses from Lake Erie and is nestled on a large lot on a quiet street. The home is comfortably furnished with an eclectic mix of antiques & mid-century modern pieces. Beautiful in any season, this property is the ideal spot for a weekend get-away or an extended stay.

Guest favourite

Guest house in Cleveland Heights

4.98 out of 5 average rating, 377 reviews

Clean and Cozy Carriage House Getaway

Sunny and cozy carriage house in safe, historic neighborhood - perfectly appointed for overnight guests or extended stay visitors. Close proximity to Cleveland Clinic, Case Western, John Carroll University, Shaker Lakes & University Circle. Enjoy the charm of staying in this premier neighborhood with the comforts of home including updated kitchen, furnishings, bed/bedding and spa shower. Beautiful, safe, tree-lined street with private entrance and parking spot.

Guest favourite

Flat in Shaker Heights

4.9 out of 5 average rating, 124 reviews

Historic District 2BR on 2nd Floor near CLE Clinic

This newly updated historic district unit is in a great location and only 15 minutes from the Cleveland Clinic main campus. Come relax in a safe but vibrant neighborhood during your stay in Cleveland. Our unit is also within a mile of plenty of great food options. This is a NON SMOKING (that includes medical marijuana, vaping, and everything else) and NO PARTY building. Please do NOT smoke or throw a party or you will be asked to leave without a refund.

Guest favourite

Flat in Northfield

4.97 out of 5 average rating, 306 reviews

Brandywine Falls Hike, Bike & Relaxation Suite

Private comfortable suite in the beautiful Cuyahoga Valley National Park. Mid-way between Cleve. & Akron. Adjacent to miles of paved walk/bike trails. Bring your bike or use rentals nearby. Visit historic villages of Hudson & Peninsula. Fine dining. Quiet Country estate setting. 5 minute walk to spectacular Brandywine Falls or rest your feet on the ottoman. Spring, Summer and Fall foliage is stunning. Among Ohios most beautiful sight seeing areas.