Entire home
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
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Reviews
9.8 out of 10
Exceptional
1 bedroom1 bathroomSleeps 346.5 sq m
Popular amenities
Explore the area

Gloucester, MA
- Place, Rocky Neck Art Colony2 min walk
- Place, Bryan Gallery5 min walk
- Place, Niles Beach16 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
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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10.0 out of 10, Exceptional, (76 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Adults only
Events
No events allowed
Pets
No pets 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
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.

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
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
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 window9.8/10
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 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
Trish C.
11 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Trish C.
Stayed 4 nights in Jun 2025
Verified
10/10 Excellent
Bailey R.
1 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Bailey R.
Stayed 3 nights in Oct 2025
Verified
10/10 Excellent
Gloria C.
25 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect!
Gloria C.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Linda E.
19 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Linda E.
Stayed 5 nights in Aug 2025
Verified
10/10 Excellent
Peter F.
11 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peter F.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Susan K.
9 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Susan K.
Stayed 5 nights in Aug 2025
Verified
10/10 Excellent
Emma S.
14 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Emma S.
Stayed 2 nights in Oct 2024
Verified
10/10 Excellent
Anthony D.
20 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anthony D.
Stayed 4 nights in Oct 2025
Verified
10/10 Excellent
Debra S.
4 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Seaside Paradise


Debra S.
Stayed 4 nights in Jul 2025
Verified
10/10 Excellent
Erica Q.
31 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
The best weekend!
Erica Q.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
Kathy M.
30 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
AIS national show in Rockport
Kathy M.
Stayed 6 nights in Sep 2024
Verified
10/10 Excellent
Marla S.
7 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful spot!
Marla S.
Stayed 2 nights in Oct 2024
Verified
10/10 Excellent
barbara d.
11 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rocky Neck Townhouse
barbara d.
Stayed 11 nights in Jul 2024
Verified
10/10 Excellent
David K.
21 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous Gloucester
David K.
Stayed 2 nights in Jun 2024
Verified
10/10 Excellent
Alan R.
19 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and great host
Alan R.
Stayed 4 nights in Aug 2024
Verified
8/10 Good
Dawn A.
23 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
What an adorable place!
Dawn A.
Stayed 2 nights in Oct 2024
Verified
4/10 Poor
Kalem M.
22 October 2025
Liked: Check-in, communication
Kalem M.
Stayed 4 nights in Oct 2025
Verified
10/10 Excellent
Mary C.
22 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Captain’s Lookout definitely lived up to our expectations
Mary C.
Stayed 3 nights in Jul 2024
Verified
10/10 Excellent
Lynn G.
30 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lynn G.
Stayed 9 nights in Sep 2025
Verified
10/10 Excellent
Elisa
3 August 2025
Liked: Cleanliness, property conditions & facilities, communication
Elisa
Stayed 6 nights in Jul 2025
Verified
10/10 Excellent
Ettore
19 June 2025
Ettore
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
Jennifer C.
16 November 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer C.
Stayed 4 nights in Oct 2024
About the host
Hosted by Elizabeth Lewis
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!
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!
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:
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