31 Chester Square, Gloucester, MA 01930

Winter Rental: Available October 1, 2025-April 30, 2026 (Utilities Included)

Located in the heart of the quaint and charming village of Annisquam, this newly... renovated Gloucester cottage offers the perfect off-season home. The bright and airy ground floor has many windows, letting in lots of natural light. The full bathroom on the main level has a shower over tub. A three-season sunroom runs the length of the house with two additional beds. The dining room is classic and formal with a drop leaf table and ceiling fan.

Upstairs, there are 3 bedrooms and a full bath with clawfoot tub and shower. All bedrooms have closet space and dressers for storage. The primary bedroom has a queen bed, bedroom two has a full, and the third has two twins.

The private back yard has garden furniture and parking both at the top and bottom of the driveway.

Take a walk back in history by strolling through the prototypical colonial village with its white clapboard and black shuttered homes and picturesque lanes that were created to accommodate horse-drawn carriages. This is what you come to New England for -- history on the water!

Dogs OK. Cats OK.
Internet and water/sewer included. Electric and gas heat included up to $400/mo.
First, last, & a half month's security deposit due at signing.
No smoking. No events or parties. Read More