Windward Guest House

The 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, With modern updates. Rooms 8 through 12  evoke memories of a simpler time with painted wood walls in soft colors, mariner quilts, and bright furnishings. Rooms 14 – 17 have been completely remodeled, while maintaining the Maine cottage feel with white-washed wood and light colors, the rooms now have vaulted ceilings, ceiling fans, sliding barn doors and built-in furniture. 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 with combination tub/showers. All rooms in the guesthouse buildings have a small refrigerator, flat-screen cable TV and air conditioning.

The 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.