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Captain’s Lookout with Harbor Views & Roof Deck

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Photo gallery for Captain’s Lookout with Harbor Views & Roof Deck

A beach with boats, a flag, and a lighthouse.
A view through a window with a clear sky, a body of water, and a residential area with houses and trees.
A balcony with wicker chairs and a table, overlooking a body of water and houses in the background.
A cozy living room with a blue sofa, a round table with a colorful tablecloth, and a staircase leading to another level.
A two-story house with a green exterior, a visible number '15', and a metal staircase leading to a balcony.

Reviews

9.8 out of 10
Exceptional

Entire home

1 bedroom1 bathroomSleeps 3

Popular amenities

  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • Parking available
  • Barbecue grill

Explore the area

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

Room options

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The price is €168
includes taxes & fees
2 Sept - 3 Sept
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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Captain’s Lookout with Harbor Views & Roof Deck

Relax at Captain’s Lookout, a charming harbor-view townhouse apartment on Gloucester’s historic Rocky Neck. Enjoy spectacular water views from the rooftop deck, sea breezes, and walkable access to beaches, galleries, restaurants, and live music. This cozy coastal retreat features three outdoor spaces, a queen Tempur-Pedic bed, strong WiFi, private parking, and easy access to scenic Wonson Cove for kayaking and paddleboarding.

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)

Availability
• 4-night minimum for weekends
• 2-night minimum during weekdays
• Weekly rentals available at discounted rates
• Available June 6 through October 31
During your stay at this vacation home, you're just a quick walk from Massachusetts Bay. The vacation home offers free WiFi and a kitchen.
  • Air-conditioned home with kitchen, patio, and living room
  • Free WiFi (speed: 500+ Mbps (good for 6+ people or 10+ devices))
  • 8 minutes by car from Good Harbor Beach and 10 minutes from Cape Ann
This vacation home offers its guests barbecue grills. The front desk is open around the clock.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Wheelchair-accessible parking and van parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 steps to reach entrance
  • Accessible parking space
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Double-glazed windows
  • Property does not allow children

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Do not to go up onto roof deck when wet with rain, snow, or ice.
Being under influence of drugs and alcohol is not advised or permitted while out on the decks or staircase.
It is not permitted to go outside the railings onto the roof or elsewhere. Landlord does not accept responsibility if injuries result.

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
Property Registration Number C0243251070

Property is also known as

3f974083-ccb4-45e1-b302-77b68a18f2eb

Captain’s Lookout with Harbor Views & Roof Deck Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 25 out of 27 reviews
Rating 8 - Good. 1 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 1 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.8/10

Cleanliness

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Trish C.

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

Terry R.

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

Bailey R.

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

Emma S.

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

Gloria C.

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

Peter F.

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

Linda E.

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
Verified review

10/10 Excellent

Susan K.

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

Erica Q.

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

Debra S.

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
Verified review

10/10 Excellent

Kathy M.

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
Verified review

10/10 Excellent

Marla S.

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
Verified review

10/10 Excellent

Anthony D.

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

barbara d.

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

David K.

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
Verified review

10/10 Excellent

Alan R.

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
Verified review

8/10 Good

Dawn A.

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

Kalem M.

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
Verified review

10/10 Excellent

Mary C.

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

Lynn G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 9 nights in Sep 2025
Verified review

10/10 Excellent

Elisa

Liked: Cleanliness, property conditions & facilities, communication
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

Ettore

Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Jennifer C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Oct 2024