Modern Luxuries With Classic Coastal Charm

Windward Guest House Topside Inn

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!

 

View of Room 8 at Topside Inn with paintings from Allen Bunker Fine Art

Room #8

  KING BED :: Windward Guesthouse :: Private Lower Level All rooms in the Windward guesthouse have been completely renovated. This ‘junior’ suite is private, roomy and beautifully appointed. Sitting

Room 9 bed

Room #9

  KING BED :: Windward Guesthouse :: First Floor All rooms in the Windward Guesthouse have been completely renovated. Spectacular water views of the harbor, islands and out to sea,

Room 10 bed and view

Room #10

  KING BED :: Windward Guesthouse :: First Floor with Easy Access All rooms in the Windward Guesthouse have been completely renovated. Nice views of the western harbor, gardens and

Room 11 bed and view

Room #11

  KING BED :: Windward Guesthouse :: First Floor with Easy Access All rooms in the Windward Guesthouse have been completely renovated. Nice views of the harbor, gardens and wooded

Room 12 bed and view

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 –

Room 14 view of bedroom

Room #14

  KING BED :: Windward Guesthouse :: Second Floor All rooms in the WIndward Guesthouse have been completely remodeled, with room 14 being one of our most popular rooms. If

Room 15 bed

Room #15

  KING BED :: Windward Guesthouse :: Second Floor All rooms in the Windward Guesthouse have been completely remodeled. Amenities: Exceptional views from the covered sitting porch and comfortable sofa

Room 16 bed and view

Room #16

  KING BED :: Windward Guesthouse :: Second Floor All rooms in the Windward Guesthouse have been completely remodeled Amenities: Exceptional views from the covered sitting porch and comfortable sofa

Room 17 bed and view

Room #17

  KING BED :: Windward Guesthouse :: Second Floor All rooms in the Windward Guesthouse have been completely remodeled. Amenities: Exceptional views from the covered sitting porch and comfortable sofa