Vacation rentals in Highland Hills

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Top-rated vacation rentals in Highland Hills

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Guest favourite

Guesthouse in University Heights

4.98 out of 5 average rating, 223 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.

Nov. 3 – 10

$182 CAD per night

Guest favourite

Guesthouse in Chardon

4.94 out of 5 average rating, 154 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.

Jul. 26 – Aug. 2

$124 CAD per night

Guest favourite

Apartment in Cleveland Heights

4.97 out of 5 average rating, 155 reviews

2nd Floor Semi Private Apartment Cleveland Heights

Near East Side. 2nd floor "in-law" apt. private bed rooms, bath, living room and kitchen and a semi-private entrance. Off-street parking and back yard grill,laundry facilities available for guest use. Close to University Circle (Case Western, Cleveland Clinic, University Hospital, many museums, Severance Hall, etc.). Great public trans access. Great for couples, solo or business travelers, small families, motorcyclists, bicyclists, and anyone who likes cats. LGBTQ, all ethnicities welcome.

Oct. 30 – Nov. 6

$120 CAD per night

Guest favourite

Apartment in Chagrin Falls

4.97 out of 5 average rating, 493 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.

Sep. 27 – Oct. 4

$163 CAD per night

Guest favourite

Cabin in Solon

4.84 out of 5 average rating, 135 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

Jul. 11 – 18

$245 CAD per night

Guest favourite

Apartment in Chagrin Falls

4.88 out of 5 average rating, 165 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.

May 17 – 24

$172 CAD per night

Guest favourite

Apartment in Cleveland Heights

4.88 out of 5 average rating, 211 reviews

Map Room I Cute Studio Near CLE Clinic, UH, CWRU

As world travelers, your hosts are fascinated by maps and have decorated the apartment with some of their favorites - both local and from around the globe. The apartment was just renovated from floor to ceiling in the summer of 2019, so you'll enjoy a brand new space that's clean and modern and has everything you need for your time in Cleveland. We're just 10 minutes from the Cleveland Clinic, Case Western Reserve University, and all the cultural treasures of University Circle.

Feb. 5 – 12

$147 CAD per night

Guest favourite

Home in Cleveland Heights

4.91 out of 5 average rating, 126 reviews

Cozy Heights Oasis-Walk to Restaurants

Private and cozy second floor 2 bedroom spacious unit in the Cedar-Lee district of Cleveland Heights. Completely refurbished. Walk to restaurants on Lee Road or Cain Park. Open the windows and listen to a chorus of birds-a true oasis from the hub-bub. A private patio and outdoor living right off the living room. Note: Quiet hours after 10 p.m. This unit is not suitable for partying, loud music and disruptive behavior that impacts neighbors or guests in other apartments.

Apr. 24 – May 1

$197 CAD per night

Guest favourite

Cabin in Euclid

4.93 out of 5 average rating, 188 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.

Sep. 6 – 13

$168 CAD per night

Guest favourite

Guesthouse in Cleveland Heights

4.98 out of 5 average rating, 371 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.

Jul. 12 – 19

$225 CAD per night

Guest favourite

Home in Cleveland Heights

4.91 out of 5 average rating, 135 reviews

Cozy Duplex in Cleveland Heights

Cozy duplex great for a weekend getaway or business stay. Very close to entertainment if you want to explore a cool and diverse neighborhood. Don't feel like going out? Stay in and host a small dinner or relax in our meditation room complete with massage table. 2 miles from Cleveland Clinic/University Hospital. Ideal for all traveling nurses and professionals looking for short term housing. Flexible with price for longer stays.

May 8 – 15

$213 CAD per night

Guest favourite

Apartment in Bedford

4.93 out of 5 average rating, 201 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.

Jan. 19 – 26

$135 CAD per night