Guest Rooms

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 the views.

 These rooms require 1 or 2 steps to access. 

Harbor View King rooms are 10, 11, 12, 19, 20 and 21.

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 the main harbor.

These rooms are located in the main house and require 1 or 2 sets of stairs to access.

Main House Queen rooms are 2, 3 and 7.

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. The rooms are bright and airy with vaulted ceilings, a ceiling fan, and recessed lighting.

These rooms have one set of stairs to access. 

Windward Select Harbor View rooms are 15, 16 and 17.

Our three Premium Harbor View King rooms, located on the top floor of the Leeward Guesthouse, feature breathtaking views of the harbor, islands, and lighthouses through a large picture window and from the private covered sitting porch. Bright and airy, these rooms have vaulted ceilings with ceiling fans. Access to these rooms are made available by ramp, which allows guests enjoy top-floor views without the need for stairs.

Leeward Premium Harbor View rooms are 23, 24 and 25.

Located in the main house on the 2nd or 3rd floors, our Main House Harbor View King room offers spectacular views of the harbor, islands, lighthouses, and sunset. The two largest rooms in the original 1865 sea captain’s home, these rooms are large, bright, and airy.

This room is located in the main house and requires 2 sets of stairs to access.

Main House Harbor View King is room 6.

With southern and westerly views, this room is believed to be the original owner’s bedroom, when the house was built in 1865. This newly renovated and refreshed guest room features beautiful harbor views, a wet room bathroom complete with a soaking tub and walk-in shower, dual vanities, a seating area, a refrigerator, and more. This romantic room is light-filled by day and met with dramatic lighting by night.

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 some of our best water views of the harbor, islands, and out to sea—especially delightful from the private covered corner sitting porch.

Windward Premium Harbor View King rooms are 9 and 14.

The Windward Junior 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 features bathing with a view—the soaking tub for two overlooks the private deck and harbor beyond. Past the sitting area is the bedroom and bathroom with double vanities and walk-in shower.

Accessibility Notes: While this is the closest room to the harbor, it is the furthest from the parking area and requires one set of stairs to access. Tall guests, please note: while large in size, this suite has lower (7′) ceilings and a center beam (6′). The Windward Junior Suite is room 8.

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, the newly renovated and beautifully furnished suite provides seclusion and privacy for a perfectly relaxing Boothbay Harbor vacation.

The Topside Leeward Suite is room 26.

The Carriage House Suite is a bright and airy space perfect for getaways, wedding preparations, and extended stays. The 600 square foot loft offers a spacious sleeping area featuring a luxurious mattress by Harrison Spinks, bathroom with tiled walk-in shower, and a separate dressing area with a second vanity. The seating area looks out across the entire bay. The kitchenette is well equipped with a wet bar with ice machine, refrigerator, microwave drawer, and Nespresso coffee maker. There is also room to get cozy next to the two-sided fireplace. Both sides have a dedicated TV.

Located directly in front of the main house, the Carriage House Suite offers a private parking space for convenient access. Guests are welcome to drive up to the main parking lot or walk across the front lawn to enjoy the main house where the breakfast is served each morning.

Please Note: A flight of stairs is required to access the Carriage House Suite.

Enjoy the comfort of our boutique cottage, featuring two bedrooms, a den/office, a full bath upstairs, and a half bath with laundry downstairs. The open living, dining, and kitchen spaces lead to a spacious deck with stunning harbor views. Only steps away from The Cottage is the Main House where you can indulge in a locally inspired full breakfast each morning during your visit. 

Perfect for two couples, especially on longer stays, the fully-equipped kitchen makes dining a breeze. The Cottage also allows private parking for two vehicles. Topside Inn is an adult-oriented property and pet-free, we’re happy to recommend nearby family and pet-friendly options.

Please contact us at (207) 633-5404 to reserve this room!