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Search results; Over 1,000 homes in Chesterland

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Top guest favourite
Home in Chesterland
Tennis House
3 bedrooms, 4 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.96 out of 5 average rating, 28 reviews
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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
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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
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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
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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
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Guest favourite
Home in Gates Mills
Greater Cleveland Modern Farmhouse Gates Mills
3 bedrooms, 3 beds, 1.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Kirtland
Kirtland, Oh 3 Bd/2 ba Parking for Camper/RV/Boat
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Chardon
Lakeview Retreat
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 157 reviews
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Guest favourite
Tiny home in Chesterland
Private Tiny House /Farm Stay/Hello Goats!
1 bedroom, 1 king bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Painesville
Great Group Getaway: Games Galore + Outdoor Oasis
7 bedrooms, 11 beds, 4.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 106 reviews
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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
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Superhost
Home in South Euclid
Pet-Friendly 3BR Retreat Near Cleveland
3 bedrooms, 3 queen beds, 1 bathroom
6–11 Sept
4.82 out of 5 average rating, 201 reviews
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Guest favourite
Home in Moreland Hills
Renovated Cottage-Game Room-Fire Pit-Sleeps 8
3 bedrooms, 5 beds, 1 bathroom
17–22 Oct
4.89 out of 5 average rating, 19 reviews
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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
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Home in South Euclid
South Euclid 3BR Cozy Home — Near Clinic
3 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.92 out of 5 average rating, 26 reviews
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Home in Chardon
Cozy Farmhouse on 13 acres
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Room in Chagrin Falls
Large Private Suite in the Chagrin Falls Area
1 queen bed, 1 bathroom
3–8 Sept
4.92 out of 5 average rating, 143 reviews
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Home in Beachwood
Stay at Supreme!
4 bedrooms, 9 beds, 3.5 bathrooms
7–12 Sept
4.86 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Chagrin Falls
Trendy upscale retreat w/hot tub
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 28 reviews