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Vacation rentals in Chesterland

Vacation rentals in Chesterland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesterland

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Modern solid log home.  Great for a quiet getaway.
    SUPERHOSTEntire cabin · 6 guests · 5 beds · 3 bathrooms
    Modern solid log home. Great for a quiet getaway.

    Cozy and spacious modern log cabin close to downtown Cleveland. Get away from the hustle of the city or recharge at night in a four bedroom, three bath, cabin on five acres with woods and a fully stocked 1/3 acre pond. Spacious kitchen w/ granite counter top, glass walk in shower, and Peloton bikes give modern conveniences without sacrificing the warmth and relaxation of a much deserved get-away. The cabin has all of the amenities of an upscale hotel while being tucked away in a quiet suburb.

    What guests are saying:

    “This home is a beautiful home with a nice scenic backyard. It feels like a secluded getaway but also has the advantage of being right near a town with everything you could need including many restaurant options. (We chose this property because we were looking for a secluded lodging that wasn't too far from Cuyahoga Valley National Park -and its about a 20 minute drive). The deck is lovely-We saw a few deer come out near the backyard pond one of the nights, and a wild turkey in the yard the day we left. The sleeping areas were perfect and our kids enjoyed having some games and toys to play with during our stay (our sons and daughter were satisfied equally). The kids also enjoyed the swing by the pond. The kitchen table has a great view of the yard and there is a lot of counter space. Another perk was having the chance to try a Peleton bike. The owners were very responsive to all of our communication. Thanks for a great trip!”

  • Lake House
    SUPERHOSTEntire house · 2 guests · 1 bed · 1 bathroom
    Lake House

    The Lake House is off by itself so you can enjoy your seclusion but we live about 200 feet away so we can assist you if you need us. It has a large kitchen and a bath with a shower. The combination living room bedroom with queen bed is perfectly situated to view the Lake and it's sunsets.

    What guests are saying:

    “Wow! Sitting on the edge of Lake Erie, this huge studio Airbnb has walk to wall stunning water views! Enjoyed the spacious deck with nice furniture & well equipped kitchen,private & quiet setting & comfy bed... we’d return here in a heartbeat. Host, Mark, was prompt & helpful in all communications. Enjoyed hiking at Mentor Lagoons Nature Preserve, Headlands State Park & wineries. Take out dinner from Tuscans (just a block from Airbnb) provided enough for meals for 2 days & was delicious!”

  • Little Italy - Heart of it all...
    SUPERHOSTEntire house · 3 guests · 1 bed · 1 bathroom
    Little Italy - Heart of it all...

    Modern, fully furnished, one-bedroom apartment (includes sofa bed for 3rd person). Set up for both short and longer comfortable stays. Cooking utensils supplied; dishwasher, gas stove & microwave; In-suite Laundry Walk, bike or take public transport (Health Line) to University Hospitals and the Cleveland Clinic or to Case Western Reserve University. Restaurants, Museums, & Specialty shops within close walking distance Off-street parking Weekly and Monthly Rates

    What guests are saying:

    “I loved staying here and wish that I wasn't just breezing through. The apartment is one of the most complete, pretty and comfortable I've stayed in. As others have noted, Linda thoughtfully leaves snacks and drinks for her guests. The Lake View Cemetery is a beautiful place to happen upon for a walk. I hope to return with my husband in tow, to explore the museums and concert halls, nearby and the neighborhood shops and restaurants when they re-open.”

Holiday rentals for every style

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Popular amenities for Chesterland holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chesterland

Cora's Cottage
SUPERHOSTEntire house
Cora's Cottage
Price:€89 / night
Cozy Room near University Circle and Downtown!
SUPERHOSTPrivate room
Cozy Room near University Circle and Downtown!
Price:€28 / night
Inviting Queen Retreat/TV in SE CLE burb (Solon)
SUPERHOSTPrivate room
Inviting Queen Retreat/TV in SE CLE burb (Solon)
Price:€31 / night
1 BR  - WiFi - self check in - heavy cleaning done
SUPERHOSTEntire flat
1 BR - WiFi - self check in - heavy cleaning done
Price:€53 / night
Brick Bungalow/Upstairs Bedroom
SUPERHOSTPrivate room
Brick Bungalow/Upstairs Bedroom
Price:€24 / night
Large Suite in the Chagrin Falls Area
SUPERHOSTPrivate room
Large Suite in the Chagrin Falls Area
Price:€44 / night
Charming Relaxing Cozy Lake Erie Getaway Cottage
SUPERHOSTEntire house
Charming Relaxing Cozy Lake Erie Getaway Cottage
Price:€66 / night
Private Room with Queen Bed & Breakfast in Aurora
SUPERHOSTPrivate room
Private Room with Queen Bed & Breakfast in Aurora
Price:€31 / night
Situated on a golf course with amazing views.
SUPERHOSTPrivate room
Situated on a golf course with amazing views.
Price:€53 / night
The Yellow Room at 291
Private room
The Yellow Room at 291
Price:€89 / night
Cozy,private whole house with Parking incl
Entire house
Cozy,private whole house with Parking incl
Price:€43 / night
Cozy & Comfortable Suite near Lake Erie
SUPERHOSTEntire house
Cozy & Comfortable Suite near Lake Erie
Price:€62 / night
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