Holiday houses in Oakwood Village

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Top-rated holiday rentals in Oakwood Village

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Guest favourite

Home in Chagrin Falls

5.0 out of 5 average rating, 199 reviews

Cottage in the Village * Walk to shops/restaurants

This cute little century home (1000 sq. ft.) is located on a quiet street just steps from the shops and restaurants in the village. Park your car and walk to the falls, grab a bite to eat, and explore. Back at the house, grab a book and read on the covered front porch, or relax in the sun on the back deck. The lower level yard has a fire ring to roast marshmallows and a circular staircase leading up to a playhouse for the kids. This cozy spot is the perfect place to be to explore Chagrin Falls!

20–27 Aug

$366 NZD per night

Guest favourite

Guesthouse in University Heights

4.98 out of 5 average rating, 226 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.

19–26 Sep

$241 NZD per night

Guest favourite

Guesthouse in Chardon

4.94 out of 5 average rating, 157 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.

30 Aug – 6 Sep

$158 NZD per night

Guest favourite

Apartment in Chagrin Falls

4.97 out of 5 average rating, 498 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.

9–16 Oct

$198 NZD per night

Guest favourite

Cabin in Solon

4.84 out of 5 average rating, 136 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

27 May – 3 Jun

$280 NZD per night

Guest favourite

Apartment in Chagrin Falls

4.88 out of 5 average rating, 168 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.

22–29 Jul

$224 NZD per night

Guest favourite

Farm stay in Peninsula

4.97 out of 5 average rating, 114 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.

22–29 Oct

$261 NZD per night

Guest favourite

Home in Parma

4.99 out of 5 average rating, 156 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!

15–22 Oct

$230 NZD per night

Guest favourite

Home in Parma

4.9 out of 5 average rating, 394 reviews

Cozy Cape Cod at Tuxedo - Self Check-In & Parking

Welcome to the coziest home Cleveland has to offer. Rest from your travels in our comfy beds, spacious living areas, 2 smart tvs, a workout room, and free parking. This home has been remodeled from top to bottom and has stylish touches throughout. The Cape Cod is on a quiet residential street with a private yard. It is minutes from downtown Cleveland, the hospital systems, the Metroparks, and more. Enjoy coffee in-house, venture to 2 nearby Starbucks, or any of Tremont's roasteries.

9–16 Oct

$212 NZD per night

Guest favourite

Cabin in Euclid

4.93 out of 5 average rating, 191 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.

8–15 Oct

$201 NZD per night

Guest favourite

Apartment in Northfield

4.97 out of 5 average rating, 303 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.

18–25 Jan

$337 NZD per night

Guest favourite

Apartment in Bedford

4.93 out of 5 average rating, 202 reviews

Quaint 1 BR Apt Above Bicycle Shop

Quiet and cozy one bedroom apartment in a historic downtown Bedford building. It is ideal for a comfortable get away that is readily accessible to the major highways in the greater Cleveland area and is easy to get to The Cuyahoga County National Park, Cleveland Metroparks and local Hospital campuses. We are located directly above a bicycle shop near several restaurants, bars and grills, coffee shops, and unique shops.

5–12 Feb

$165 NZD per night