Captain's Lookout | Roof Deck & Harbor Views

Photo gallery for Captain's Lookout | Roof Deck & Harbor Views

A residential area with houses, a dock, and a body of water in the background.
A two-story house with a spiral staircase, a porch, and a small garden area.
A cozy living room with a blue sofa, two armchairs, and a wooden coffee table. There are framed pictures on the wall, a mirror, and a window with curtains.
A kitchen with white cabinets, a stainless steel refrigerator, and a dining table with chairs.
A room with a large window, a table with chairs, and a lamp.

Reviews

9.8 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Niles Beach

Popular amenities

  • Balcony
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Laundry room

Explore the area

View in a map
Gloucester, MA
  • Place, Rocky Neck Art Colony
    ‪2 min walk‬
  • Place, The Gorton Theatre
    ‪5 min walk‬
  • Place, Niles Beach
    ‪16 min walk‬
  • Airport, Beverly, MA (BVY-Beverly Municipal)
    ‪29 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed

Living Room 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms
Dining area

Add dates for prices

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About the area

Gloucester

Located near the beach, this apartment is in Rocky Neck, a neighbourhood in Gloucester. Ten Pound Lighthouse and Eastern Point Lighthouse are local landmarks, and the area's natural beauty can be seen at Ravenswood Park and Thatcher Island National Wildlife Refuge. Rocky Neck Art Colony and Maritime Gloucester are also worth visiting. Scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and ecotours nearby.
Map
Gloucester, MA

What's nearby

  • Massachusetts Bay - 1 min walk - 0.0 km
  • Rocky Neck Art Colony - 2 min walk - 0.2 km
  • The Gorton Theatre - 5 min walk - 0.5 km
  • Niles Beach - 16 min walk - 1.4 km
  • Good Harbor Beach - 4 min drive - 3.3 km

Getting around

  • Gloucester Station - 11 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 28 min drive

Restaurants

  • ‪The Lobster of Gloucester - ‬2 min drive
  • ‪Seaport Grille - ‬5 min drive
  • ‪Dunkin' - ‬5 min drive
  • ‪The Burn Tavern - ‬5 min drive
  • ‪Mom's Kitchen - ‬6 min drive

Frequently asked questions

Is Captain's Lookout | Roof Deck & Harbor Views pet-friendly?

No, pets are not allowed at this property.

How much is parking at Captain's Lookout | Roof Deck & Harbor Views?

On-site parking is available at the property.

What time is check-in at Captain's Lookout | Roof Deck & Harbor Views?

Check-in begins at 4:00 PM.

What time is check-out at Captain's Lookout | Roof Deck & Harbor Views?

Checkout is at 10:00 AM.

Where is Captain's Lookout | Roof Deck & Harbor Views located?

Located in Rocky Neck, this apartment building is steps away from Massachusetts Bay and Rocky Neck Art Colony. Ten Pound Lighthouse and Niles Beach are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 30 out of 32 reviews
Rating 8 - Good. 1 out of 32 reviews
Rating 6 - Okay. 0 out of 32 reviews
Rating 4 - Poor. 1 out of 32 reviews
Rating 2 - Terrible. 0 out of 32 reviews

10/10

Cleanliness

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time! Clean, cozy and plenty to do within walking distance. A beautiful fall getaway even if it was a nor’easter! Very quiet neighborhood, many great restaurants close by! Loved it, thank you Tom & Elizabeth!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
It was very beautiful, comfortable and very clean.The parking was tight, but fine for smaller cars
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The rental was extremely clean and had everything we needed. The hosts were so friendly and very communicative which made our stay perfect. I would definitely recommend this rental and will be coming back!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay at Captain's Lookout was delightful. The decks provided great views and the house was clean and cozy. The neighborhood was peaceful and Captain's Lookout was the perfect place to unwind after spending a day in bustling Gloucester and the surrounding area. It was fun to be able to walk to art galleries, restaurants and even a local ice cream shop.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Captain's Lookout is a tiny bit of heaven!
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the views from all the decks! Quiet location and minutes to downtown Gloucester! House is adorable!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

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.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

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.
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful little place on a quiet street in a perfect spot. Thank you
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Aug 2025
Response from VrboOwner on 3 Sept 2025
So glad you enjoyed your stay, Linda and thank you! Yes, there are many lovely walks within short drives. I would also venture to say that many (including myself) also enjoy walking "around the Neck", looking at the paint factory (a Gloucester Harbor landmark), homes, gardens, art galleries and water views that abound! One can spend just 5 minutes or much longer, if exploring all the little streets on Rocky Neck.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

The best weekend!

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
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

AIS national show in Rockport

Cozy and comfortable. Missing a tv remote and instructions for departure. Great location. Everything we needed 👍
Stayed 6 nights in Sep 2024
Response from VrboOwner on 10 Oct 2024
Glad you found it comfortable and cozy! Actually, the TV remote is unnecessary, as we've been told by the cable company. So we put it out of sight to avoid confusion. Check out info is in VRBO, which you may not have had access to if you didn't bring your computer or log in info. We'll put something in the new guestbook. Thanks for pointing that out!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Seaside Paradise

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!
Stayed 4 nights in Jul 2025
Response from VrboOwner on 19 Aug 2025
Thank you, we love it when people not only enjoy being in Gloucester but enjoy our little neighborhood as well! There are so many special things about Rocky Neck and we’re glad you took advantage of a little beach around the corner :-)! Happy that you found beach chairs in the back of the house, and the beach towels to use as well! Happy to know you’ll be back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful spot!

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!
Stayed 2 nights in Oct 2024
Response from VrboOwner on 22 Oct 2024
We love to hear when people have a good time and enjoy our place. Thanks Marla! We think it's pretty special to be on "the Neck", with water in most directions and with wide water views from the roof deck. And we try to make everything comfortable and pretty. (The bed is a tempur-pedic, by the way!).
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rocky Neck Townhouse

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.
Stayed 11 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous Gloucester

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!
Stayed 2 nights in Jun 2024
Response from VrboOwner on 21 Jun 2024
I’m so happy you folks had a good time, David! I love to know when people take full advantage of both being on Rocky Neck, on Cape Ann and simply being on North Shore! :-). Thanks so much for leaving some great suggestions for others to do, both here and also in the guest notebook.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Workspaces weren't loud or noisy in the slightest.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and great host

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.
Stayed 4 nights in Aug 2024
Response from VrboOwner on 30 Sept 2024
We're so glad you and your wife had a good time, Alan! We try to make the property as inviting and pleasant as possible.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

What an adorable place!

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!
Stayed 2 nights in Oct 2024
Verified review

4/10 Poor

Liked: Check-in, communication
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.
Stayed 4 nights in Oct 2025
Response from VrboOwner on 5 Nov 2025
I appreciate your comments and always try to learn and improve so that my guest's experiences are great. To be honest, this is a surprising "first" in terms of displeasure. I'm sorry if you didn't enjoy your stay and that you had to experience the negativity of a neighbor who usually keeps to herself. She was upset that you blocked her in to her own driveway. Her driveway is next door to and on the other side of my house. My driveway is the one that goes right along the entry to my house, as you learned. I will try to make that more clear-we're working on a video. The house was freshly painted last year, as well as having many other upgrades. There is no water damage to the walls. I describe the house as being "quirky" and rightly so as the it is over 100 years old. As far as unlevel floors, the bedroom floor has some little dips, but with the new carpeting, even my 97 year old Mom did fine on it this summer! I think I have represented it well in the descriptions. People usually report it being better than expected. Again, I'm sorry if that wasn't your experience.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Captain’s Lookout definitely lived up to our expectations

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.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This quiet beautiful little place was perfect for my husband and I. The roof balcony was beautiful for sunrises and sunsets. Very convenient to the commuter train and close to great places to eat and amazing views. Thank you for such a cozy place.
Stayed 5 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing time! Place was fantastic! Neighbors were friendly, it was quaint and very quiet. Will be back!!
Stayed 7 nights in Jul 2026
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