Comfortable Accommodations on the Western Hillside

Drone view of the Leeward Guest House at Topside Inn

The Leeward Guesthouse 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!

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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 Guesthouse rooms below and find the perfect space for your Boothbay Harbor getaway!

Room 19, Windward Guest House, king bed with luxury firm mattress, tub/shower combination in the private bath

Room #19

  KING BED :: Leeward Guesthouse :: First Floor with Easy Access All rooms in the Leeward Guesthouse have been completely renovated Amenities: End room with extra west-facing window and

The bed inside Room 20 at the Topside Inn

Room #20

  KING BED :: Leeward Guesthouse :: First Floor with Easy Access All rooms in the Leeward Guesthouse have been completely renovated Amenities: Beautifully appointed room with original artwork and

Room 21, Windward Guest House, King bed with luxury firm mattress, private bathroom with walk-in shower

Room #21

  KING BED :: Leeward Guesthouse :: First Floor with Easy Access All rooms in the Leeward Guesthouse have been completely renovated Amenities: Beautifully appointed room with original artwork and

King bed with luxury firm mattress

Room #23

  KING BED :: Leeward Guesthouse :: Top Floor with Easy Access :: End Room with Corner Balcony All rooms in the Leeward Guesthouse have been recently renovated Amenities: Great

LED Fireplace

Room #24

  KING BED :: Leeward Guesthouse :: Top Floor with Easy Access All rooms in the Leeward Guesthouse have been recently renovated Amenities: Great views of the harbor, islands and

King Bed with luxury firm mattress

Room #25

KING BED :: Leeward Guesthouse :: Top Floor with Easy Access All rooms in the Leeward Guesthouse have been recently renovated Amenities: Great views of the harbor, islands and lighthouses

Suite

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