Modern Luxuries With Classic Coastal Charm

Windward Guest House Topside Inn

The Windward Guest House 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 Guest House 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 Completely renovated in 2018, this ‘junior’ suite is private, roomy and beautifully appointed. Sitting room with comfortable seating area, coffee

Enjoy spectacular views from this coveted corner room, with a king bed and tub/shower combination

Room #9

  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

Plenty of sunshine enters the room, a ideal place to relax and unwind

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 Completely renovated for

A king bed with a custom headboard, wood panel walls are featured in this modern guest room

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. Completely renovated in

This guest room has plenty of natural light to showcase its modern furnishing and vaulted ceiling.

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 –

Coveted corner room in the Windward Guest House, with lots of natural sunlight, vaulted ceilings and a luxury firm mattress

Room #14

  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

Room 15, Windward Guest House, King bed with tub/shower combination

Room #15

  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

The bed inside Room 16 in the Windward Guest House at Topside Inn

Room #16

  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.

The bed inside Room 17 at the Topside Inn

Room #17

  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