Get a Room!
Topside Inn offers a unique variety of stylish, comfortable, in-town accommodations spread among the historic Main House and two summer guesthouses named Windward and Leeward.
All guestrooms offer views of the water that vary from glimpses of the inner harbor and famous footbridge, to broad stunning views southward overlooking the islands and out to sea across two lighthouses.
All rooms are non-smoking and include private in-suite baths, cable TV, free wireless internet and local phone calls, bath amenities, hairdryers, irons and ironing boards. Some rooms have special features as noted on the reservation website.
It's true, we don't have air conditioning—and hardly ever need it—with normal summer highs in the upper 70s, and our spot at the top of the hill attracting an almost constant sea breeze. All rooms have fans to help circulate the ocean air. And yes, guestrooms do have heat!
Main House (rooms 1 - 7)
A classic Maine seacoast home from 1864, the large porch welcomes you to the the historic main house from three directions, offering 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 upper levels have three guestrooms on each floor. Rooms are accessed from interior hallways and each room is unique in size, shape, features and decor.
The very best views are from rooms 3, 4, 6 and 7, the front-facing rooms on the second and third floors. Room 2 has a delightful postcard view of the inner harbor and famous footbridge.
Windward Guest House (rooms 8 - 17)
Windward sits at the west edge of the front lawn, closest to the outer harbor view. Capturing the spirit of a Maine summer cottage, the rooms evoke memories of a simpler time with painted wood walls in soft colors, mariner quilts and bright furnishings. All rooms have private baths, and direct access to the shared porches that stretch across the front and back.
The entrances to most rooms are visible from the lawn: rooms 9 - 12 run left to right along the the first floor, and rooms 14 - 17 comprise the second floor above. At the far end of the building, a stairway leads down to room 8, nestled on the hidden lower level. The very best views in Windward are from rooms 8, 9, and 14.
Leeward Guest House (rooms 19 - 25)
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.
The top floor rooms 23 - 25 offer great views south and west including Burnt Island and the Cuckolds lighthouses. Rooms 19 and 20 share the same vista from a lower vantage point. Each room features a picture window of the southwestern view, and space on the sitting porch to enjoy the outdoors.
All of Leeward's well-sized rooms include a refrigerator, second sink outside the bathroom, and ample closet space.
