Captain’s Lookout with Harbor Views & Roof Deck

Lovely stay! The rooftop patio has an amazing view :) Got to have a quick interaction with the host right as I was jetting off to catch my flight and she was very sweet!

House is super small. Very “ quirky “. Walls are water damaged. Floors have multiple dips and unlevel. Has a very fall apart feel to it. The fold out bed is almost impossible to use. Owner has left little notes EVERYWHERE . Neighbors were incredibly rude. Instructions say to park at rear, we used the drive way opposite of the front door, which apparently was the wrong one. Neighbor was BEATING on the door in the morning, very unhappy. After she yelled at us, we moved, apologized and didn’t make the mistake again. I still got a message from the owner the following morning about not using her drive way, and only allowed one vehicle, even though we only had one car. End of the day, you can get much more bang for your buck, with a lot less fear of falling through a floor.

Workspaces weren't loud or noisy in the slightest.

Loved the views from all the decks! Quiet location and minutes to downtown Gloucester! House is adorable!

Charming townhome perfect for my get-away. Lovely casual decor, spotless, with all needed amenties, ideal location with views of the ocean. I sought a quiet place for writing with access to options for wqlks, which were easily accessible within 5-10 min drives. The owner was cooperative & helpful— would highly recommend.

Had a great time at Captain's Lookout! This adorable house was beautifully clean and had every amenity we could have wanted. It was in a great location, in walking distance to a couple of great restaurants on the harbor and many galleries, and in near driving distance to all of Gloucester, Bass Rocks, and Rockport. There is so much to do there! We had a great time, and would definitely book this again if we're in the Cape Ann area. Thank you!

This is a very inviting property in a beautiful neighborhood. The home is lovely and homey, equipped with everything we needed. We loved walking around the area, felt very safe and not much traffic. There’s a nice beach just a two minute walk from home. There were even beach chairs and towels for guest. The owners thought of everything and pleasantly. We’ll be back!

Captain's Lookout is a tiny bit of heaven!

Captain’s Lookout is a gem! It was beautiful, clean, comfortable and had so many inviting spaces to relax and enjoy. The owners seem to go the extra mile to make it a really pleasant stay. I thoroughly enjoyed our time there.

Beautiful little place on a quiet street in a perfect spot. Thank you

We had so much fun!! This house was so so great the patio was the perfect place to relax and enjoy the sea air after a long day. Our trip was for Salem but I definitely want to go back this summer just for the house! This was such a seamless and lovely stay

Quick mother/daughter trip so that we could head into Salem and enjoy time. Adorable cottage style and perfect for 2 people. Futon worked for my teen. Parking is tight behind house if you have a large vehicle, this is not a knock, just a point of awareness. Views and the rooftop access are a huge bonus. I did not locate any wifi, but we really didn't stay in - there is to much to see! I would stay there again and thanks to the host!

We had a great time at Captains lookout. The pictures were accurate and we love the view from the roof. The host was very accommodating and helpful.

We had a lovely weekend stay at this Rocky Neck cottage. Most spectacular, unique. rooftop views of the harbor coupled with comfy bed, nice bathroom, well-equipped kitchen, and two additional porches for outdoor enjoyment. Peaceful and quiet, but a short drive to downtown Gloucester, we did a lot of local biking, eating, relaxing, and exploring. Thanks for a great stay! Highly recommend!

Cozy and comfortable. Missing a tv remote and instructions for departure. Great location. Everything we needed ?

My wife and I stayed for several days and the apartment was perfect for our needs. Everything in the apartment was spotless, fresh linens and soft towels. The multiple decks offer a variety of places to sit, read and listen to the ocean. The neighborhood was super safe and quiet; you could hear a pin drop at night and the breeze off the ocean was delightful. We enjoyed the local beaches, had dinner with friends at Tonnos and breakfast at the Source bakery. Rockport is a short drive and there are many other great shopping areas. Communication with the owner was easy and we had a lovely stay.

We stayed a week in this adorable, artsy townhouse, which has outdoor decks on three floors (top floor is a widow watch). It was perfect for kayaking, as the launch was 20 feet away. Also good for walking to restaurants, art shops and seafood markets. Comfortable and convenient.

This was the perfect respite for us. As an artist I have wanted to visit Rocky Neck to find inspiration for new work. This cute little townhouse was right in the heart of Rocky Neck and just the right size for two of us. The description and photos were an accurate depiction of the cozy cottage feel of this townhouse. We had breakfast on the porch in the morning. The bed and bath were upstairs with plenty of closet space for clothes and such. The bed was very comfortable. The bathroom clean and newly updated. The porch off of the bedroom has an upper level with great 360 views of the harbor and neighborhood. We could walk to the galleries and restaurants and the Cultural Center is right down the hill with exhibits and concerts on Thursday nights in the summer. I was able to set up and paint right up the street from where we were staying. The neighbors were all very nice. We had dinner on the outer deck at 51 Rocky Neck and lunch a few times at Duckworth’s. The North Shore Art Association was also a destination, a .75mile walk over the bridge. Gloucester was a short drive where we visited the Cape Ann Museum and had dinner at Tonno, one of our favorite spots whenever we come to Cape Ann. We also visited the Sleeper, McCann House up the street from the Rocky Neck area. We will definitely return to Rocky Neck and hope to stay at Captain’s Lookout on our next trip.

Rocky Neck is a hidden gem- quaint neighborhood, gorgeous views, and a cozy, eclectic home away from home at Captain’s Lookout. Host left us a warm welcome and everything we needed for a wonderful stay. We attended the Prescott Park music festival in Portsmouth, explored Rockport, had seafood at Woodman’s in Essex, a sunset cruise on Gloucester’s Schooner Lannon. Morning walks past galleries and beaches, and quiet evenings on the porch made our seaside getaway a dream!