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"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Photo gallery for "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Dine on the roof deck with a great views! (There are 4 chairs)
Captain's Lookout! Front door, 2nd floor deck, spiral stairs and roof deck.
View toward the small boat launch area at end of street, from roof deck.
Broader view of kitchen and dining, from couch. Patio doors to left.
Renovated dining and kitchen areas. TV can be rotated toward wall to "minimize"

Reviews

9.8 out of 10
Exceptional
1 bedroom1 bathroomSleeps 346.5 sq m

Popular amenities

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

Explore the area

View 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)
    ‪24 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 · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Enjoy the ambiance of a New England Seaside Getaway, without the crowds!

Quick Note: We have a two night minimum stay Sunday through Thursday, and a five night minimum for any rentals that include Friday and or Saturday night.

This lovely, romantic townhouse sits near the water with fantastic views of Gloucester Harbor, especially from the middle and rooftop decks.

Located on a quiet side street in the seaside neighborhood of Rocky Neck, a peninsula that hangs out into Gloucester Harbor. The house is on a very private, and quiet street which ends at the water where there is a boat ramp (about 80 feet from the property). Here, you can launch your kayak, canoe, or paddle-board (nothing larger).

Rocky Neck is a fun, festive art colony with many active music-filled restaurants and art galleries. The Gloucester Stage Company is a 7 minute walk. There is a small beach around the corner for swimming, and Good Harbor Beach, one of the top beaches on the North Shore, is just 7 minutes away by car.

This townhouse is the front unit of a two-family house. I’ve been renting the rear townhouse for over 30 years. Visit https://www.vrbo.com/181237 to see the reviews (Ranked “Exceptional” with a rating of 9.8/10, and over 60 reviews).

Second Floor Bedroom
• Queen-sized bed with a TempurPedic mattress
• Second floor deck and roof deck access are off the bedroom.
• Black-out curtains
• Plenty of storage space in bedroom closet and bureau.

Bathroom
• Second floor, off bedroom
• Tub/shower combo.
• It has been upgraded in the past year with beautiful accents.
• Bathroom has space for your essentials.

Kitchen
• Recently updated with a new fridge, microwave, and toaster oven as well as other conveniences, including a Keurig or coffeemaker.
• All the pots, pans, and dishes you may need are there, including non-breakables for decks!
• Sun deck just outside kitchen door with table, 4 chairs and umbrella.


General Info
• There are three choice locations to relax and eat outside at the Captain's Lookout: on the pretty sun deck off the kitchen/living room, at the middle deck off the bedroom, or on the roof deck where the views are fantastic!
• High quality linens for bed and bath.
• There are a few antique furnishings and/or artwork in the house, some collected by "the captain", in her worldwide travels! Most of the artwork in the downstairs is by Rocky Neck Artists!

Parking
• Private parking for your one car. (Shared with the other unit - room for 2 cars total).

Miscellaneous
• Easily sleeps two but can accommodate 3-4 (family or good friends), with full-size sleep sofa.
• The whole unit has central AC, plus there’s a ceiling fan in the bedroom. The sea breezes from Gloucester Harbor often create a lovely freshness to the place, so you can turn off the AC and open the windows to let in the breeze!
• New Samsung Smart TV with multiple cable channels. Premium channels not included, but Netflix, Prime, etc. is easily accessed. Roku is available, please enquire.
• There is a two burner gas grill on the sun deck by the kitchen, and if you need something bigger, there is a four burner gas grill at the back of the building, Grilling tools are provided.
• There is a laundromat about a ½ mile away and cleaning supplies are provided in the townhouse, if needed.
• This is a safe and friendly area where people often don't even lock doors! But I prefer that you lock anyway. There is an outdoor key box.

It is a great getaway for a couple or single person to enjoy the summer in this lovely area. Gloucester and Cape Ann abound with many cultural and recreational activities. In Gloucester, enjoy whale watching, large sailboat cruises and many cultural activities and events from Saint Peter's Fiesta in late June to the Tall Ships Parade and Mayor's Cup Race over Labor Day. Nearby in Rockport you can browse around Bear Skin Neck, view incredible scenery including "Motif #1", explore Halibut Point State Park, attend a concert at the Rockport Music-Shalin Liu Performance Center or a dance performance at Windhover in Rockport. There are plenty things to do on Cape Ann!

Times to some destinations:
Rocky Neck Art Colony - 3-4 min walk
Niles Beach - 12 min walk
Maritime Gloucester - 5 min drive
Cape Ann Museum - 6 min drive
Good Harbor Beach - 7 min drive
Boston Logan International Airport (BOS) – 56 min drive
Beverly Regional Airport (BVY) – 24 min drive

And as always, the beauty of nature and all its opportunities for exercise and recreation, still abound.

This is available for:
June through October with reduced rates for stays of over 7 days. Also available as a winter rental (see Craig's list).

Keywords: Townhouse, Water Views, New Listing

Add dates for prices

Amenities

Kitchen
Free WiFi
Air conditioning
Outdoor space
Parking available
Barbecue

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
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.

Important information

You need to know

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
Property Registration Number C0243251070

We should mention

This property does not have any lifts

About the area

Gloucester

Rocky Neck, a neighbourhood in Gloucester, is home to this holiday home. Eastern Point Lighthouse and Sargent House Museum 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.
View more Holiday homes in GloucesterOpens in a new window
Map
Gloucester, MA

What's nearby

  • Rocky Neck Art Colony - 2 min walk - 0.2 km
  • Bryan Gallery - 5 min walk - 0.4 km
  • The Gorton Theatre - 5 min walk - 0.5 km
  • Niles Beach - 16 min walk - 1.4 km
  • Schooner Adventure - 2 min drive - 2.5 km

Getting around

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

Restaurants

  • ‪Dunkin' - ‬5 min drive
  • ‪Source Bakery - ‬5 min drive
  • ‪Blue Collar Lobster Co. - ‬5 min drive
  • ‪Tonno Restaurant - ‬6 min drive
  • ‪Minglewood Tavern - ‬5 min drive

Frequently asked questions

Is "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester?

As of 26 Mar 2026, prices found for a 1-night stay for 2 adults at "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester on 10 June 2026 start from AU$320, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester?

On-site parking is available at the property.

What time is check-in at "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester?

Check-in begins at 4:00 PM.

What time is check-out at "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester?

Checkout is at 10:00 AM.

Where is "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester located?

Located in Rocky Neck, this holiday home is within a 10-minute walk of Rocky Neck Art Colony, Bryan Gallery and The Gorton Theatre. Niles Beach and Massachusetts Bay are also within 1 mile (2 km).

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. 21 out of 23 reviews
Rating 8 - Good. 1 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 1 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Lynn G.

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

10/10 Excellent

Elisa

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

10/10 Excellent

Ettore

Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Jennifer C.

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

About the host

Hosted by Elizabeth Lewis

Host profile image
I'm a physical therapist who is currently working full time in my private practice. I love this area for all it's charm and natural beauty, the abundance and availability of outdoor recreation, it's culture and it's quirky, artsy people! When I'm not working, I sometimes go paddle boarding out on Gloucester Harbor or take advantage of this beautiful area in other as. I now am living in Ipswich with my new husband, Tom, where we enjoy hiking on trails in some of the many conservation areas the North Shore offers. We often come to Gloucester and stay in the front town house for a couple of days, as that used to be my home and I can't be far from that very special area for long in the summer. We can be reached if you have any questions or concerns.

We really hope you enjoy your stay!

Why they chose this property

I decided to buy a vacation rental in this location because I wanted to spend time on Cape Ann, especially Rocky Neck, which is a beautiful and unique place year round.

What makes this property unique

Staying at this property is wonderful. As described in the listing, there are water views from the property and beautiful views all around, just steps away. You will find that the place is quiet, clean and charming and as many artists have said, the light is unique on Rocky Neck (and Cape Ann), which is why it attracts many artists. Almost any road on Rocky Neck has some kind of view of the water, so you can see great beauty from dawn to dusk and then there's the night sky....!

There are lots of fun things to do just an easy walk away from the property on Rocky Neck in the summer, as it's still a flourishing 'art colony'.

You will enjoy taking walks to several beaches, from here. It's just great!

Languages:

English

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