Overview
Topside Inn offers a unique variety of in-town accommodations spread among the main house and two summer guesthouses, named Windward and Leeward.
All rooms are non-smoking and include private in-suite baths, cable TV and dial-out telephone with free local calls. We have wireless internet in public areas for laptop users. Some rooms have additional features, such as refrigerators in the Leeward guesthouse or VCRs in the main house rooms. There's free parking, a shuffleboard court, croquet, and chairs to sit and enjoy the view—in sun or shade.
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. A fan can be found in every room, and heat as well!
Main House Rooms
The main house is open from early May until the end of October. The rooms are detailed below, including relevant personality traits—it's an old house and each room is unique in size, shape, features and decor.
Room 1: Our only first floor guestroom is just off the entry hall. Two huge window bays on the front porch offer views across the lawn to the ocean, and down the hill to the inner harbor. A king bed (new in 2008), nice sitting area with comfortable easy chairs, and full bath.
Room 2: At the rear of the second floor, a queen bed with great view of the footbridge and inner harbor. The full bath has a perfect view of sunset. A small dressing room in back includes a second sink, closet and bureau.
Room 3: In the southeast front corner, second floor with amazing harbor and ocean views. A charming room with black iron queen bed set in the window bay, soothing colors, hardwood floor, extra large bathroom with a tile and glass block shower.
Room 4: The big room, second floor with incredible water and sunset views. A romantic king bed, lots of room to spread out, extra large bathroom with two separate vanity areas. This is the one that returning guests ask for first!
Room 5: Upstairs at the rear of the third floor, our smallest room has a postcard view of the famous footbridge over the inner harbor. A very cozy spot for a single only, the bathroom shower is short in height so this room is NOT for tall people.
Room 6: The front view from the top is breathtaking - lounge in the window seat staring out to sea, or in the king bed, watching the inner harbor. Cool green colors, a spacious room, and a vaulted ceiling in the bathroom.
Room 7: From the window seat in front, you'll find an ocean view you can't take your eyes from. Unless you're looking out the side windows at the sunset. A wonderful top corner room with a queen bed and a generous-sized bath.
Windward Guest House
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.
Eight rooms are visible from the lawn: Rooms 9 - 12 on the first floor and Rooms 14 - 17 above. At the far end a stairway leads down to Room 8. Rooms 8, 9, and 14 have southern exposure windows facing the outer harbor and ocean view.
The second floor rooms (like Room 14 pictured here) have one queen bed. Each room has a distinct design and all enjoy views from the covered back porch.
The first floor rooms have either two beds or king. On the ends, rooms 9 and 12 each have a queen and twin bed, great for three or a couple needing a second bed. In the center of the building, room 10 has a king and room 11 two doubles. As the center pair of doors are together, rooms 10 and 11 create the closest situation we have for adjoining rooms, without the interior connection.
As the hill behind Windward slopes away, Room 8 is the hidden gem on the lower level. This unique unit includes a private deck with water view, a sitting room open to a king bedroom, and large bath with double vanity. A refrigerator and microwave are tucked in one of the closets.
Leeward Guest House
Perched at the edge of the wooded western hillside, Leeward is actually an addition to the property's original cottage. It expands from a single story at the edge of our parking area, into a 3-story building with five additional guestrooms.
The three rooms on the top floor are accessible with minimal stairs, but offer the height to enjoy a great view fo the harbor and islands through the picture window. There is also a nice spot on the sitting porch for each room to continue enjoying the view.
The middle level rooms enter on the view side of the building, and are really two stories off ground. These two rooms, one with king and the other two doubles, also include sitting porch space with water view at the entrance to each room.
All of Leeward's well-sized rooms include a refrigerator, second sink outside the bathroom, and ample closet space.
Room 23 is the top floor end unit, four stories off the ground and with views of the western harbor and the incredible sunset.
Room 25 is another great spot to rest comfortably and enjoy the sitting porch. This room is neighbor to the innkeepers' quarters - not just anyone gets to stay here!