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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
Superhost
Home in Gates Mills
Luxurious Hidden Gem in Suburbs of Cleveland OH
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
4.67 out of 5 average rating, 3 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
Room in Mayfield
Comfy and Cozy! One bedroom in a beautiful house!
2 queen beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 3 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 Chagrin Falls
Your Chagrin Falls Village Home Away From Home
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.95 out of 5 average rating, 158 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, 165 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
Top guest favourite
Home in Chardon
Historic Century Home on Chardon Square
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 76 reviews
Guest favourite
Home in Chagrin Falls
The May House | Walk to Chagrin Falls + Hot Tub
2 bedrooms, 2 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chagrin Falls
Trendy upscale retreat w/hot tub
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 29 reviews
Home in Burton
Graham Keller House
3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Chagrin Falls
Curran’s Crossing-#1- Queen bed-private entrance
1 queen bed, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 174 reviews
Top guest favourite
Home in Chardon
Lakeview Retreat
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 159 reviews
Guest favourite
Home in Shaker Heights
5-BR Colonial, King Bed, Main Floor BR, Pool Table
5 bedrooms, 8 beds, 3.5 bathrooms
7–12 Sept
4.82 out of 5 average rating, 88 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
Guest favourite
Flat in Chagrin Falls
Cozy Solar Powered Hideaway (Pet Friendly)
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.87 out of 5 average rating, 255 reviews