WindwardThe Windward House sits at the west edge of the front lawn, closest to the outer harbor view and just steps away from the Main House.

Capturing the spirit of a Maine summer cottage, these rooms evoke memories of a simpler time with painted wood walls in soft colors, mariner quilts, and bright furnishings. Windward rooms 9 – 17 are accessed directly from the outside via covered porches that overlook the lawn and eastern side of the harbor. Each of these rooms also has access out the back door to a covered porch facing the harbor, western coves and sunset. The built in comfortable banquettes and new cable railings provide a great place to relax and take in the view.

Viewed from the lawn, Rooms 9 – 12 are left to right along the main level, and upstairs Rooms 14 – 17 comprise the second floor. All have private in-suite bathrooms – modestly sized but efficient with combination tub/showers. All rooms in the guesthouse buildings have a small refrigerator, flat-screen cable TV and air conditioning.

Windward PorchThe end rooms have the advantage of three extra windows in the side walls, giving Rooms 9 and 14 magnificent “laying-in-bed” views of the harbor, and bringing lots of extra light from the gardens to Rooms 12 and 17.

At the far end of the building, a stairway leads down to Room 8: a gem on the hidden lower level. Room 8 takes advantage of the walk-out level with a large private deck and covered sitting porch. Inside there is a sitting room, king-bed, air conditioning and large bathroom. Room 8 may be short on ceiling height, but it is high on privacy and space with a nice view over the historic Boothbay Boatyard.

Windward-Guesthouse-Room-8

Room #8

KING BED :: Windward Guesthouse :: Private Lower Level A hidden spot situated alone on the entire lower level Spacious open-air deck exclusively for your room Sitting room with comfortable

Room #9

KING BED :: Windward Guesthouse :: First Floor with Easy Access Spectacular water views of the harbor, islands and out to sea, plus more from the covered sitting porch Coveted

Room #10

KING BED :: Windward Guesthouse :: First Floor with Easy Access Nice views of the western harbor, gardens and wooded hillside from the covered sitting porch KING bed with light

Windward Porch

Room #11

1 KING BED :: Windward Guesthouse :: First Floor with Easy Access Nice views of the harbor, gardens and wooded hillside from the covered sitting porch. 1 KING bed with

Room #12

KING BED :: Windward Guesthouse :: First Floor with Easy Access Nice views of the western harbor, gardens and wooded hillside from the covered sitting porch End room – very

Room #14

KING BED :: Windward Guesthouse :: Second Floor One of our most popular rooms, being completely remodeled for the 2017 season. Exceptional “laying in bed” water views of the harbor,

Room #15

KING BED :: Windward Guesthouse :: Second Floor Rooms 14 – 17 are being completely remodeled for the 2017 season (ready by May 5th opening) Exceptional views from the covered

Room #16

KING BED :: Windward Guesthouse :: Second Floor Rooms 14 – 17 are being completely remodeled for the 2017 season (ready by May 5th opening) Exceptional views from the covered

Room #17

KING BED :: Windward Guesthouse :: Second Floor Rooms 14 – 17 are being completely remodeled for the 2017 season (ready by May 5th opening) Exceptional views from the covered