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Search results; Over 1,000 homes in Chesterland

Superhost
Tiny home in Chesterland
Private Tiny House /Farm Stay/Hello Goats!
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.91 out of 5 average rating, 171 reviews
Top guest favourite
Home in Chesterland
Tennis House
3 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chesterland
*MUST SEE* Spacious & Private Colonial
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Kirtland
Relaxing Lakeview, Boating, Fishing, & Bonfire!
6 bedrooms, 7 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Chardon
Avonlea Gardens & Inn - Entire House
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Superhost
Home in Gates Mills
Luxurious Hidden Gem in Suburbs of Cleveland OH
4 bedrooms, 4 beds, 4.5 bathrooms
6–11 Sept
New place to stay
Top guest favourite
Home in Chardon
Lakeview Retreat
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 159 reviews
Top guest favourite
Room in Kirtland
House in the woods
4 beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 85 reviews
Guest favourite
Cottage in Kirtland
Willow Woods Retreat | Historic Farmhouse + Pond
4 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.8 out of 5 average rating, 198 reviews
Top guest favourite
Home in Chardon
Cozy Farmhouse on 13 acres
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Cottage in Chagrin Falls
Iron Works Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 164 reviews
Top guest favourite
Flat in Chagrin Falls
The Mill House
2 bedrooms, 2 queen beds, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Home in Kirtland
Kirtland, Oh 3 Bd/2 ba Parking for Camper/RV/Boat
3 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Room in Chagrin Falls
Large Private Suite in the Chagrin Falls Area
1 queen bed, 1 bathroom
14–19 Oct
4.92 out of 5 average rating, 143 reviews
Top guest favourite
Home in Painesville
Great Group Getaway: Games Galore + Outdoor Oasis
7 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
4.95 out of 5 average rating, 107 reviews
Guest favourite
Home in Cleveland
Log Cabin I Nature's Oasis I Fire Pit + Gazebo
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.85 out of 5 average rating, 86 reviews
Top guest favourite
Home in Mentor
Super Upscale Ranch!
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 273 reviews
Top guest favourite
Home in Mentor
Cozy Renovated Ranch, 3 Bed, 1.5 Bath
3 bedrooms, 3 beds, 1.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Chagrin Falls
Bright, Spacious 3-Bed Retreat/Walkable to Village
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 36 reviews