Comfortable Accommodations on the Western Hillside

Drone view of the Leeward Guest House at Topside Inn

The Leeward Guest House is an addition to the original carriage house at Topside Inn. It’s home to six rooms and a suite that all feature coastal decor and modern amenities. Plus, each room includes a private covered porch with cozy chairs that are perfect for sitting outside and taking in the scenery.

Rooms 19, 20 and 21 offer glimpses of the harbor over our newly planted orchard as well as a convenient entrance and sitting porch on the south side of the building. Rooms 23, 24, and 25 offer bright and airy spaces with 11-foot vaulted ceilings, king beds, walk-in showers, LED image fireplaces, and stunning views. Even though they’re on the top floor, Leeward’s hillside location lets you enter without having to climb any stairs!

For peaceful retreats with plenty of privacy, we recommend the suite. It has 14-foot vaulted ceilings with skylights, a gas fireplace, full kitchen, king bed, and a large master bathroom with a glass shower and separate soaking tub. What more could you ask for?

Explore the Leeward Guest House rooms below and find the perfect space for your Boothbay Harbor getaway!

Room #19

  KING BED :: Leeward Guesthouse :: Middle Floor with Easy Access Room 19 is a beautiful corner room in Leeward Guesthouse. Enjoy a scenic sunset from the luxurious king

Room #20

  King Bed :: Leeward Guesthouse :: Middle Floor with Easy Access Offers partial harbor views, as well as views of the lower lawn, gardens and newly planted orchard from

Room #21

  KING BED :: Leeward Guesthouse :: First Floor This newly renovated and beautifully furnished first-floor room has been completely redone with wood paneling on ceiling and walls, recessed lighting, all

Room 23

Room #23

  KING BED :: Leeward Guesthouse :: Top Floor with Easy Access :: End Room with Corner Balcony This gorgeous corner room has been newly renovated for the 2019 season,

Bedroom with king-size bed at Topside Inn

Room #24

  KING BED :: Leeward Guesthouse :: Top Floor with Easy Access This beautiful guest room has been newly renovated for the 2019 season and is located on the top

Bed and Nightstand

Room #25

KING BED :: Leeward Guesthouse :: Top Floor with Easy Access Check Availability This beautiful room has been newly renovated for the 2019 season. From this top-floor room in the

Suite

KING BED :: Leeward Guesthouse :: Second Floor with Private Access Check Availability This newly renovated and beautifully furnished suite provides seclusion and privacy for a perfectly relaxing Boothbay Harbor vacation.