Vacation rentals in Chesterland

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Popular amenities for Chesterland vacation rentals

Stay near Chesterland's top sights

Guido's Pizza Haven, Restaurant, and Preferred Catering Service4 locals recommend
Oak & Embers Tavern3 locals recommend
Red, Wine & Brew - Chesterland3 locals recommend

Other great vacation rentals in Chesterland

Superhost
Home in Parma
4.88 out of 5 average rating, 8 reviews

Beautiful spacious home for your next gathering

MariaRating, 5 stars2 weeks ago
The house was very clean, roomy and comfortable. Great location to stores, restaurants, etc. Highly recommend if you have a large group - we had 6.
Top guest favorite
Cabin in Hinckley
5 out of 5 average rating, 23 reviews

Vacation Home with Hot Tub

KyleRating, 5 stars1 month ago
Photos don’t do this place justice! There’s plenty of outdoor space to gather and relax. The additional building was perfect for our group—we spent most of our time there. The host was very responsive to all our questions. With its great location near Cleveland and excellent amenities, we’ll definitely be back!
Guest favorite
Home in Medina
4.97 out of 5 average rating, 114 reviews

Medina 57 - Easy walk to Medina Historic District

AliceRating, 5 stars3 weeks ago
We had a wonderful time staying here! It was a great location to visit Cuyahoga Valley NP and within walking distance of the cute downtown area. Our kids also loved the yard! A huge space that was perfect for kids of all ages with a small play structure and room to run around and explore.
Top guest favorite
Cottage in Geneva
4.93 out of 5 average rating, 69 reviews

Dylan's Light House (Sunshine cottages)

ChristinaRating, 5 stars8 months ago
If you're looking for a charming getaway, Dylan's Lighthouse is a delightful choice! The place is quaint and so cute! The cleanliness was impeccable, making our stay both comfortable and worry-free. One of the highlights of our stay was the inviting outdoor space. We spent both evenings relaxing around the fire pit. Location-wise, Dylan's Lighthouse is conveniently close to the strip, so we had easy access to popular restaurants and bars. Even better, we could walk to the nightlife, which was incredibly convenient and a real treat for us! David, the owner, was so friendly and responsive, always quick to answer our questions and offer helpful recommendations. In summary, Dylan's Lighthouse is a gem of a place with wonderful hosts, and we highly recommend it for anyone looking for a peaceful retreat with easy access to local amenities.
Top guest favorite
Cottage in Geneva
5 out of 5 average rating, 16 reviews

GOTL Family Cottage: kitchen, ctrl HVAC,14 guests

MarkRating, 5 stars7 months ago
Nice place, we would stay there if in town again
Top guest favorite
Home in Medina
5 out of 5 average rating, 48 reviews

The Chelsea of Medina | Walk to Historic Square

JerryRating, 5 stars2 weeks ago
Story book home with perfect location. This was by far the best Air BnB we've stayed at. From the immaculate cleanliness to the comfortable beds and even the condition of the walls and floors. We bought some walnuts in the shall for the squirrels in the expansive back yard. Hopefully we don't get in trouble for feeding the squirrels ;)
Top guest favorite
Apartment in Downtown Cleveland
5 out of 5 average rating, 11 reviews

City Getaway | Free Parking | 24/7 Hour Gym

LouisRating, 5 stars1 week ago
Beautiful location,very nicely appointed.
Top guest favorite
Home in Ashtabula
4.96 out of 5 average rating, 101 reviews

Point Break 3 BR near beach, dining, and shopping

ImariRating, 5 stars2 weeks ago
Very nice, very comfortable! Walking distance to downtown love the fact that they were recommendations for restaurants and things to do. I hadn’t been to Walnut Park since I was a kid so it was amazing being able to walk to. It will definitely be staying again.

Destinations to explore

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  2. United States
  3. Ohio
  4. Geauga County
  5. Chesterland