Perched on the edge of the wooded western hillside, Leeward is an addition to the property’s original guest cottage (now the new suite (room #26), offering relaxed bed and breakfast lodging at our coastal Maine inn. When viewed as one structure from the front lawn, it expands from a single story at the edge of our front parking area into a 3-story building at the far end, providing access to rooms on all levels without climbing flights of stairs.

On the top floor, Rooms 23 – 25 offer bright and airy rooms with 11 foot vaulted ceilings with light pickled wood finish and ceiling fans, king beds and great views to the south and west, including Burnt Island and the Cuckolds lighthouses. The suite offers 14 foot vaulted ceilings with skylights, gas fireplace, full open kitchen, master bedroom with king bed and large bathroom with glass shower and separate soaking tub. Just a few steps up from ground level, rooms are entered from a walkway along the north side of the building – top floor rooms with no stairs! Each room features a picture window of the view, and a back door from each leads to the shared sitting covered porch with privacy dividers, new cable railings and comfortable chairs.

Rooms 19, 20 and 21 offer glimpses of the harbor, with entry and sitting porch on the south side of the building.

Rooms 19 and 20 include a refrigerator, a second sink outside the private en-suite bathroom with combination tub/shower, and ample closet space. Room 21 has been completely remodeled with wood paneled walls and ceilings, recessed lighting, glass shower and a ceramic oyster shell vessel sink created by local artist Alison Evans.

Room 19

Room #19

KING BED :: Leeward Guesthouse :: Middle Floor with Easy Access Check Availability Room 19 is a beautiful corner room in Leeward Guesthouse. Enjoy a scenic sunset from the luxurious

Room #20

King Bed :: Leeward Guesthouse :: Middle Floor with Easy Access Check Availability Offers partial harbor views, as well as views of the lower lawn, gardens and newly planted orchard

Room #21

KING BED :: Leeward Guesthouse :: First Floor Check Availability This newly renovated and beautifully furnished first-floor room has been completely redone with wood paneling on ceiling and walls, recessed lighting,

Room 23

Room #23

KING BED :: Leeward Guesthouse :: Top Floor with Easy Access :: End Room with Corner Balcony Check Availability This gorgeous newly renovated corner room offers breathtaking harbor views, vaulted

Bedroom with King Bed

Room #24

KING BED :: Leeward Guesthouse :: Top Floor with Easy Access Check Availability This beautiful Leeward room is located on the top floor, complete with breathtaking views of the harbor,

Bed and Nightstand

Room #25

KING BED :: Leeward Guesthouse :: Top Floor with Easy Access Check Availability From this beautiful top-floor Leeward Guesthouse room you can enjoy breathtaking views of the harbor, bright vaulted

Suite

KING BED :: Leeward Guesthouse :: Second Floor with Private Access Check Availability This newly renovated and beautifully furnished suite provides seclusion and privacy for a perfectly relaxing Boothbay Harbor vacation.