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.

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 from room 17

Windward Select Harbor View

Located on the top floor of the Windward Guesthouse, our three Windward Select Harbor View King rooms feature exceptional views from the covered sitting porch with a built-in sectional sofa.

Room 19 bedroom

Harbor View King

  Located on the lower levels of the Windward and Leeward Guesthouses, our six Harbor View King rooms overlook the gardens and harbor and offer private, covered porches to enjoy

Room 14 bedroom

Windward Premium Harbor View King

The Premium Harbor View King rooms are located in our Windward guesthouse and are two of our most popular rooms on the property. Very light, bright, and airy, each offers

Room 8

Windward Jr. Suite

The Windward Jr. Suite is private, spacious, and beautifully appointed. Enter the room from the 180 sq/ft open-air private deck overlooking the harbor. The sitting area right inside the door