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Search results; Over 1,000 homes in Chesterland

Guest favourite
Tiny home in Chesterland
Private Tiny House /Farm Stay/Hello Goats!
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 166 reviews
Top guest favourite
Home in Chesterland
*MUST SEE* Spacious & Private Colonial
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Home in Chesterland
Tennis House
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Chardon
Lakeview Retreat
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Home in Chardon
Avonlea Gardens & Inn - Bluebell Suite
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Kirtland
Relaxing Lakeview, Boating, Fishing, & Bonfire!
6 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Garrettsville
“Willow Ledge at Silver Creek”with Private Hot Tub
2 bedrooms, 2 king beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 561 reviews
Guest favourite
Home in Cleveland
Log Cabin I Nature's Oasis I Fire Pit + Gazebo
3 bedrooms, 4 beds, 1.5 bathrooms
31 Aug – 5 Sept
4.84 out of 5 average rating, 82 reviews
Guest favourite
Flat in Chagrin Falls
Cozy Solar Powered Hideaway (Pet Friendly)
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 252 reviews
Top guest favourite
Guest house in Chardon
Chardon Loft
1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 346 reviews
Home in Chagrin Falls
The May House | Walk to Chagrin Falls + Hot Tub
2 bedrooms, 2 beds, 2 bathrooms
16–21 Oct
Top guest favourite
Flat in Chagrin Falls
Cozy Apartment in Charming Village
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 650 reviews
Top guest favourite
Cottage in Willowick
Lake House with Amazing Views
1 king bed, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 341 reviews
Superhost
Home in Eastlake
Modern & Stylish | Cozy 3BR Home w/ hot tub
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.79 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Newbury Township
The Loft
1 bedroom, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Loft in Chagrin Falls
Your Main Street Studio
2 beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 153 reviews
Top guest favourite
Home in Chardon
Exhale...
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
4.99 out of 5 average rating, 125 reviews
Top guest favourite
Campsite in Chardon
Rustic Rock Lake Cabin
1 bedroom, 2 bunk beds, No bathroom
16–21 Aug
4.99 out of 5 average rating, 157 reviews
Superhost
Home in Euclid
Elinore Estates
4 bedrooms, 4 queen beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews