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

Chesterland house rentals

We found 110 house rentals — enter your dates for availability

Explore Chesterland house rentals

Image of -MUST SEE- Spacious Chesterland Colonial

-MUST SEE- Spacious Chesterland Colonial

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Image of Peaceful Historic Home on 10 Acres w/ Lake, Barn & Fire Pit - 5 Bedrooms

Premier Host

Peaceful Historic Home on 10 Acres w/ Lake, Barn & Fire Pit - 5 Bedrooms

Sleeps 10 · 6 bedrooms · 2+ bathrooms

Image of Private Peacful 4000 sq. home

Private Peacful 4000 sq. home

Sleeps 6 · 3 bedrooms · 3+ bathrooms

Image of The Thistle House off Chardon Square

Premier Host

The Thistle House off Chardon Square

Sleeps 10 · 4 bedrooms · 2 bathrooms

Image of Family 3BR Home King Bed Close to Everything

Family 3BR Home King Bed Close to Everything

Sleeps 5 · 3 bedrooms · 1 bathroom

Image of Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Premier Host

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Sleeps 6 · 3 bedrooms · 0+ bathrooms

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