Modern Luxuries With Classic Coastal Charm

The Windward Guesthouse sits at the western edge of our front lawn, just steps away from the Main House. It captures the spirit of a Maine summer cottage with plenty of modern updates.
We completely remodeled the Windward rooms while preserving their coastal feel with white-washed wood, light colors, sliding barn doors, and built-in furniture. All of them have private en-suite bathrooms with combination tubs and showers, small refrigerators, and flat-screen TVs. Rooms 14 through 17 on the second floor also feature vaulted ceilings.
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You can access Rooms 9 through 17 via covered porches that overlook the lawn and eastern side of the harbor. They also provide access to a covered porch facing the harbor, western coves, and sunset. The built-in banquettes and cable railings make it a fantastic place to relax and take in the views. The end rooms feature three extra windows, giving Rooms 9 and 14 magnificent views of the harbor and Rooms 12 and 17 plenty of natural light from the gardens. Room 8 is a gem on the lower level with a large private sundeck, covered porch, king-size bed, and large bathroom. It’s big on privacy and space with a beautiful view of the historic Boothbay Boatyard.
Scroll down to explore the Windward Guesthouse and find your ideal retreat!
KING BED :: Windward Guesthouse :: Private Lower Level Completely renovated in 2018, this ‘junior’ suite is private, roomy and beautifully appointed. Sitting room with comfortable seating area, coffee …
KING BED :: Windward Guesthouse :: Completely in Spring 2018 Spectacular water views of the harbor, islands and out to sea, plus more from the covered sitting porch Coveted …
KING BED :: Windward Guesthouse :: First Floor with Easy Access Nice views of the western harbor, gardens and wooded hillside from the covered sitting porch Completely renovated for …
1 KING BED :: Windward Guesthouse :: First Floor with Easy Access Nice views of the harbor, gardens and wooded hillside from the covered sitting porch. Completely renovated in …
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 – …
KING BED :: Windward Guesthouse :: Second Floor Room #14 was completely remodeled for the 2017 season and is one of our most popular rooms. If you are looking …
KING BED :: Windward Guesthouse :: Second Floor This gorgeous Windward Guesthouse room, Room #15, was completely remodeled for the 2017 season. Enjoy breathtaking harbor views from this room and …
KING BED :: Windward Guesthouse :: Second Floor Rooms #16 was completely remodeled for the 2017 season. This bright room features a King bed, vaulted ceilings, and great views. …
KING BED :: Windward Guesthouse :: Second Floor This beautiful corner room was completely remodeled for the 2017 season. From Room 17, you can enjoy gorgeous harbor views from your sitting …