A calm river with boats, wooden docks, and buildings along the shore.

Chester cottage rentals

We found 74 cottage rentals — enter your dates for availability

Explore Chester cottage rentals

Image of Updated cottage "Beriozka" on Cedar Lake

Premier Host

Updated cottage "Beriozka" on Cedar Lake

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of The little cottage on the ct river

Premier Host

The little cottage on the ct river

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of 1-bedroom cottage with Grove Beach 🏖️ access.

Premier Host

1-bedroom cottage with Grove Beach 🏖️ access.

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Saybrook Point Cottage - Charming and Private

Premier Host

Saybrook Point Cottage - Charming and Private

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Lovely Cottage by Lake Hayward

Premier Host

Lovely Cottage by Lake Hayward

Sleeps 7 · 3 bedrooms · 1 bathroom

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value