Search Guest Houses in Chesterland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Chesterland guest houses

1. Tall Oaks Resort

Tall Oaks Resort
4.0 star property
Willoughby
9.4 out of 10, Exceptional, (37 reviews)
"The facility was extremely clean & well maintained. We were the only people staying on the property (no staff) so that was different. Instructions were clear for accessing our room, etc."
United States
Gina
The price is Rp2.695.261
Rp3.665.421 total
includes taxes & fees
9 Nov - 10 Nov
Tall Oaks Resort

2. Steele Mansion

Steele Mansion
3.5 star property
Painesville
10.0 out of 10, Exceptional, (475 reviews)
"I was impressed with how well maintained the property is and the historyI would definitely visit again."
United States
Susan
The price is Rp3.313.905
Rp3.819.311 total
includes taxes & fees
9 Nov - 10 Nov
Steele Mansion

3. Stone Gables Inn

Stone Gables Inn
2.0 star property
Ohio City
9.6 out of 10, Exceptional, (354 reviews)
"Great location!"
United States
Stephen
The price is Rp2.134.502
Rp2.720.947 total
includes taxes & fees
9 Nov - 10 Nov
Stone Gables Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chesterland

Maple syrup flows freely at Patterson Fruit Farm, where families pick seasonal produce and enjoy fresh-baked treats. Explore the Western Reserve's rural charm at Holden Arboretum in nearby Kirtland, or sample local wines along the Grand River Valley wine trail.

A wooden bridge over a snow-covered path in a forest.