Captain's Lookout | Roof Deck & Harbor Views

Enjoy relaxing coastal living at Captain’s Lookout, a charming loft-style townhouse apartment located on Gloucester’s historic Rocky Neck, surrounded by the waters of Gloucester Harbor.

This private two-story apartment offers beautiful harbor views, sea breezes, and three separate outdoor spaces—including a rooftop deck with spectacular water views.

Perfect for couples, solo travelers, or a small group of up to three guests, the apartment combines classic Cape Ann charm with comfort, privacy, and walkable access to beaches, restaurants, galleries, and live music.

The space

This bright loft-style apartment features an open-concept living, dining, and kitchen area on the first floor, with a private upstairs bedroom and adjoining bath.

Enjoy water views from every level:
• Rooftop deck with spectacular water views, outdoor dining table and seating for four — perfect for cocktails, dinner, or stargazing
• Private “coffee deck” off the bedroom
• Ground-floor deck off the living area with outdoor table and seating for four
Sleeping arrangements:
• Upstairs bedroom with queen Tempur-Pedic mattress and adjoining bathroom
• Queen sleeper sofa in the living room
Please note that the upstairs bathroom is accessed through the bedroom, making the space best suited for couples or close friends rather than multiple couples or families with young children.

Amenities include:
• Quality linens and blackout shades
• Samsung 34" Smart TV with streaming access for your favorite services
• Keurig coffee maker
• Strong WiFi
• Beach chairs
• Private parking for one vehicle
• Central air conditioning and heat
• Ceiling fan and natural ocean breezes
• Gas grill
• Guest information book with local recommendations

Neighborhood highlights:
• A short walk to a small swimmable beach
• Small public launch area approximately 130 feet from the house for SUPs, kayaks, and canoes
• Easy access to scenic Wonson Cove, a peaceful and fun part of Gloucester Harbor

Wonson Cove is tidal, creating a unique coastal experience. At low tide you can walk out onto the flats, while mid-to-high tide is ideal for launching kayaks, canoes, and paddleboards.

• Walkable restaurants, galleries, and live music on Rocky Neck
• Nearby theater company and cultural events throughout Gloucester and Cape Ann

Gloucester and nearby Rockport offer whale watches, sailing excursions, beaches, hiking, art galleries, live music, and coastal New England charm throughout the summer season. Guests can explore Bearskin Neck, Halibut Point State Park, the Shalin Liu Performance Center, and seasonal events including Saint Peter’s Fiesta and the Gloucester Schooner Festival.

Parking:
• One private off-street parking space included
• Due to the narrow layout of this historic waterfront neighborhood, additional parking is not available directly on the street near the property
• Additional vehicles may park nearby on adjacent streets or in the free municipal parking lot approximately a 4-minute walk away

Laundry:
• The basement and laundry area are not part of the standard rental space
• Laundry access may be available for guests staying one week or longer upon request
• A nearby laundromat is located approximately ½ mile away (about a 3-minute drive)

Available June 6 through October 31.

Rental options:
• 3-night minimum for weekends
• 2-night minimum during weekdays
• Weekly rentals available at discounted rates