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Topside Inn offers a unique variety of stylish, comfortable, in-town lodging in Boothbay Harbor, Maine. Accommodations are spread among the historic Main House and two summer guesthouses named Windward and Leeward. The diversity of these buildings means that there's something for everyone - from large and luxurious rooms with "laying-in-bed" views of the ocean, to more modest spaces with scenic views from the sitting porch.

Our hilltop location offers something that you won't find in area hotels. Surrounded on three sides by water, it is all about the view, and you'll find one in every room: from glimpses of the inner harbor and famous footbridge, to broad stunning views southward overlooking the islands and out to sea across two lighthouses, over to the western cove and sunset.

All guestrooms include private in-suite baths, cable TV, complimentary wireless Internet, bath amenities, plush towels, hairdryers, irons and ironing boards. Bedding includes crisp sheets, plenty of pillows, and extra blankets on the closet shelf for cool nights. Special features are listed in each room's details on the reservation system, so if you need your own refrigerator, or are concerned about stairs, look for those specifics when you check availability.

It's true, some of our rooms don't have air conditioning. We hardly ever need it, with normal summer highs in the upper 70s and lows in the 50s, and our spot at the top of the hill attracting an almost constant sea breeze. Some of our returning guests would never consider using it when here, regardless of the weather. But to keep stride with the needs for some guests, Windward rooms (#8 - #17) have air conditioning!  All rooms have fans to help circulate the ocean air. And yes, guestrooms do have heat!


A classic Maine seacoast home from 1840, the large porch welcomes you to the the historic main house with views across the lawn, above the harbor, into the sea beyond. Inside, the first level includes common areas, dining room, the front desk, and Room 1. The second floor has three guest rooms, and the third floor has two guest rooms plus a great lookout from the center dormer.


Windward sits at the west edge of the front lawn, closest to the outer harbor view. Capturing the spirit of a Maine summer cottage, rooms with modern comforts evoke memories of a simpler time. All rooms have private baths, and direct access to the shared porches that stretch across the front and back. Windward rooms are air conditioned!


Perched on the edge of the wooded western hillside, Leeward (the left side of the building in this picture) is an addition to the property's original cottage (the smaller portion to the right). Viewed as one structure from the front lawn, it expands from a single story at the edge of our parking area into a 3-story building, providing access to rooms on all levels without climbing flights of stairs.