Dock View

3 Bed | 2 Bath | Sleeps 6

113 Commercial Street
Boothbay Harbor, Maine 04538

Lake House and Dock

Lake House

2 Bed I 2 Bath I Sleeps 4
208 Lakeside Drive
Boothbay Harbor, Maine 04538

View from room 17

Windward Select Harbor View

Located on the top floor of the Windward Guesthouse, our three Windward Select Harbor View King rooms feature exceptional views from the covered sitting porch with a built-in sectional sofa.

View of the outside of 129 Commercial Street, the Boat House

Boat House

3 Bed | 2 Bath | Sleeps 7

129 Commercial Street
Boothbay Harbor, Maine 04538

Relax and unwind in room 3.

Main House Queen

  Located in the main house on the 2nd or 3rd floors, our three Main House Queen rooms feature easterly views over town and inner harbor or southerly views over

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

Room 6 window view

Main House Harbor View King

Located in the main house on the 2nd or 3rd floors, our two Main House Harbor View King rooms offer spectacular views of the harbor, islands, lighthouses, and sunset. The

Room 14 bedroom

Windward Premium Harbor View King

The Premium Harbor View King rooms are located in our Windward guesthouse and are two of our most popular rooms on the property. Very light, bright, and airy, each offers

Room 8

Windward Jr. Suite

The Windward Jr. Suite is private, spacious, and beautifully appointed. Enter the room from the 180 sq/ft open-air private deck overlooking the harbor. The sitting area right inside the door

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,