Title: "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester Vacation home in Gloucester with kitchen and patio ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102180000/102170900/102170825/459fa095.jpg?impolicy=resizecrop&rw=598&ra=fit) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102180000/102170900/102170825/613fe0f8.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102180000/102170900/102170825/54ba4187.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Beach](https://images.trvl-media.com/lodging/103000000/102180000/102170900/102170825/9ba645e1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102180000/102170900/102170825/f29c5811.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Close to Good Harbor Beach, "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester has plenty to offer. Stay connected with free in-room WiFi. 10 Exceptional ### Entire home 1 bedroom1 bathroomSleeps 3500 sq ft ## Popular amenities - Parking available - Air conditioning - Barbecue grill - Outdoor space - Kitchen - Free WiFi ## Add dates for prices Check-in Check-out Travellers ## 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" 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 ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transportation - Wheelchair-accessible parking and van parking available ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Electric kettle - Ice maker - Lobster/crab pot - Microwave - Oven - Refrigerator - Stovetop ### Bedrooms - Bedroom - Bedsheets provided ### Bathroom - 1 bathroom - Bathtub or shower - Hair dryer - Shampoo - Soap - Toilet paper - Towels provided ### 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. - 1 accessible parking space - 2 steps to reach entrance - Area rugs in public areas - Hardwood flooring in public areas - Upper floors accessible by stairs only - Wheelchair-accessible parking - Wheelchair-accessible van parking - Smoking not allowed ### 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 - Unit size: 500 square feet ## Similar properties ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34390000/34385600/34385554/dc3573e0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester Gloucester, - Ocean view - Kitchen - Free WiFi - Air conditioning 9.8 Exceptional 80 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&selected=34385554&PinnedHotelID=34385554&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, books](https://images.trvl-media.com/lodging/102000000/101200000/101198600/101198528/6b159726.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy two bedroom house in the heart of Gloucester Gloucester - Kitchen - Washer - Dryer - Free WiFi 9.6 Exceptional 12 reviews CA $201 CA $436 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03&selected=101198528&PinnedHotelID=101198528&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95810000/95805300/95805292/48d58349.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Shore Cottage - Coastal gem, a traveler favorite! 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Cottage on Whittier, new construction Marblehead - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 140 reviews CA $399 CA $589 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&selected=60638080&PinnedHotelID=60638080&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 ### 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 Pets not 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 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 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 Property Registration Number C0243251070 ### We should mention This property does not have elevators ## About the area Gloucester is home to this vacation home. The area's natural beauty can be seen at Good Harbor Beach and Cape Ann. Schooner Adventure and Maritime Gloucester are also worth visiting. [Visit our Gloucester travel guide](https://www.expedia.ca/Gloucester.dx8008) [View more Vacation homes in Gloucester](https://www.expedia.ca/Gloucester-Private-Vacation-Homes.d8008-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C42.60398%2C-70.65799&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=oJwTTlRfhbcxAJG-4WWryW51DTg=) Gloucester, MA ### What's nearby - Rocky Neck Art Colony - 2 min walk - 0.2 km - Good Harbor Beach - 4 min drive - 2.9 km - Maritime Gloucester - 4 min drive - 3.2 km - Half Moon Beach - 6 min drive - 5.0 km - Wingaersheek Beach - 14 min drive - 12.5 km ### Getting around - Gloucester Station - 11 min drive - Beverly, MA (BVY-Beverly Municipal) - 28 min drive ### Restaurants - ‪Source Bakery - ‬5 min drive - ‪Dunkin' - ‬5 min drive - ‪Blue Collar Lobster Co. - ‬5 min drive - ‪Oak To Ember - ‬5 min drive - ‪Drift - ‬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. ### 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? > Check-out is at 10:00 AM. ### Where is "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester located? > Situated in Gloucester, this vacation home is within a 5-minute walk of Rocky Neck Art Colony and Ten Pound Lighthouse. Bryan Gallery and Niles Beach are also within 15 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 9.8 Location ### 10 Property conditions & facilities 10 - Excellent 18 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### Trish C. Jul 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Captain's Lookout is a tiny bit of heaven! ##### Trish C. Stayed 4 nights in Jun 2025 ### 10/10 Excellent #### Gloria C. Jun 25, 2025 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. ##### Gloria C. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Peter F. Jun 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Beautiful little place on a quiet street in a perfect spot. Thank you ##### Peter F. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Emma S. Oct 14, 2024 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. ##### Emma S. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Erica Q. Oct 31, 2024 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 ##### Erica Q. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Kathy M. Sep 30, 2024 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 👍 ##### Kathy M. Stayed 6 nights in Sep 2024 ### 10/10 Excellent #### Marla S. Oct 7, 2024 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! ##### Marla S. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### barbara d. Aug 11, 2024 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. ##### barbara d. Stayed 11 nights in Jul 2024 ### 10/10 Excellent #### David K. Jun 21, 2024 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! ##### David K. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Alan R. Aug 19, 2024 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. ##### Alan R. Stayed 4 nights in Aug 2024 ### 8/10 Good #### Dawn A. Oct 23, 2024 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! ##### Dawn A. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Mary C. Jul 22, 2024 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. ##### Mary C. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Elisa Aug 3, 2025 Liked: Cleanliness, property conditions & facilities, communication ##### Elisa Stayed 6 nights in Jul 2025 ### 10/10 Excellent #### Ettore Jun 19, 2025 ##### Ettore Stayed 3 nights in Jun 2025 ### 10/10 Excellent #### Jennifer C. Nov 16, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Jennifer C. 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