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!

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 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 25 bed and view

Leeward Premium Harbor View

  Our three Premium Harbor View King rooms, located in the Leeward Guesthouse, feature beautiful views of the harbor, islands, and lighthouses through a large picture window and from the

The view of the living area in the Suite at Topside Inn

Topside Leeward Suite

Located in our Leeward Guesthouse, this is our largest suite on the property and fantastic for longer stays or luxurious getaways. With a full kitchen, living room, and separate bedroom,