Entire home

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

Photo gallery for WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

A wooden deck with wicker chairs and a small table, a sliding glass door leading to a covered patio area, and a view of a lake and buildings in the distance.
A sunroom with wicker furniture, large windows, and a view of a cityscape and water.
A cozy living room with a fireplace, wicker chairs, and a view of the outdoors.
A modern kitchen with a central island, stainless steel appliances, and a view to the outside.
A harbor with boats docked, a red building, and a white building with a grey roof.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
Overlooking the ocean, this vacation home features 3 bedrooms and 2 bathrooms, accommodating 6 guests. Enjoy adventure activities like windsurfing and kayaking nearby. The outdoor patio offers a great space for relaxation, while golf options nearby support active pursuits. Visit attractions such as Schooner Adventure and Capt Bill & Sons Whale Watch.

Highlights

  • Made for relaxation

    Top-rated for comfort — guests feel right at home here.
  • Garage parking available

    Enjoy the convenience of garage parking - a rare offering in the area.
  • Centrally-located

    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks

    Close to Cape Ann Museum
3 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Toys
  • Garage parking available
  • Gas grill
  • Patio
  • Washer
  • Air conditioning

Explore the area

View in a map
Gloucester, MA
  • Place, Capt Bill & Sons Whale Watch
    ‪8 min walk‬
  • Place, Cape Ann Museum
    ‪8 min walk‬
  • Place, Maritime Gloucester
    ‪10 min walk‬
  • Airport, Boston, MA (BNH-Boston Harbor Seaplane Base)
    ‪61 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Twin Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only · Jetted bathtub

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Garden

About this property

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all things is the sunroom chaise overlooking the harbor, but there are also two spacious desk areas including one in the living room which can be closed off for privacy while your family enjoys the rest of the house! (Then, of course, go to the beach!) Vaccination preferred, though no longer required.

WELCOME
From this convenient in-town location enjoy restful refinement while also delighting in being part of the Gloucester experience. This 2800 sq ft, easy-to-live-in home is perched above the sparkling waters of Gloucester's inner harbor. Watch the gulls soar and fishing boats return from the comfort of your enclosed sunporch or adjacent outdoor deck, family room or spacious, fully-equipped kitchen. Or fire up some tasty burgers on our new gas grill on the patio overlooking the garden.

Walk an easy five to ten minutes to great restaurants, our favorite whale watch boat, schooner sailing, harbor water shuttle, fun and funky shops, and maritime and art museums. In a five minute drive, you can also be at Good Harbor Beach, Niles Beach, Rocky Neck Art Colony or the commuter rail to Boston.

With a peaceful décor and open floor plan, guests tell us this is an especially comfortable place to call home. On the main floor, all overlooking Gloucester's inner harbor are the sunroom, adjacent outdoor porch, family room and fully-equipped kitchen; plus there are a half bath, formal dining room and living room with a baby grand piano. Upstairs are three bedrooms, two full baths, and laundry. The master bedroom with en suite bath overlooks the inner harbor and has a king bed, reading chairs and desk area. Your other two bedrooms include one with a queen bed, and one with two twins. These rooms share the adjacent hall bath with double vanity sinks. Ceiling vented, room-controlled Air Conditioning and ceiling fans in all bedrooms. Family Room/Kitchen area also has a ceiling fan and split AC/Heat unit for any unusually hot days.

BASIC DETAILS
When you arrive, on the kitchen island you’ll find a garage door opener, extra keys, house and travel directions (including wifi code); a list of favorite restaurants, activities, and links to explore local events, plus brochures for fun activities around town and in Boston.

FAMILY ROOM
Enjoy wireless internet, a 55" flat-screen Smart TV in the family room, books and games, Bose wireless speakers to listen to your favorite music from your phone or computer. Smart TV is loaded with Netflix and Amazon Prime free videos and music. Or load your subscription streaming services. (Be sure to log out when you depart.)

KITCHEN & DINING
Our kitchen is well-equipped so it's easy to 'eat-in' if you wish.
Seating for four on the kitchen island; seating for six in the dining room. Lovely linens, dishes, silver, glassware...
You are welcome to use the spices you'll find in the kitchen.
There's also a Weber gas grill on the patio in the back yard - available early Spring thru late Fall.

GARAGE & PARKING
The garage under the house holds two carefully parked medium-sized cars or one larger car. There is also easy, free, on-street parking on Friend St. Beach equipment is in the garage for you. (Beach chairs, 2 kid chairs, coolers, toys and pails, noodles, boogie boards for the kids.) Beach towels are in the linen closet upstairs.

TELL US ABOUT YOU!
When inquiring please tell me something about yourself, what brings you to Gloucester, and what you love to do. It will help me know you a bit better and it also helps me have some sense of the kinds of activities I might recommend for you while visiting. About a week before your reservation I'll send you a welcome note with Arrival Tips (address, unloading, parking . . . ) plus highlights of Special Events happening while you are with us. Nice people of all races, cultures, faiths, sexual preference and political views are welcome here.

CHECK-IN & DEPARTURE: Check-in any time after 3PM / Check-out by 11 AM.

RESERVATIONS & PAYMENT: Available online via VRBO. They will add a 4-9% service fee to your rental fee. 25% of fees are due at time of reservation. Balance due 60 days prior to arrival. VRBO will send you payment reminders.

LIABILITY & DAMAGES: You agree that the homeowner is not responsible for any accident, injury or illness that occurs to you or anyone in your party. Only guests or visitors agreed to at the time of your making the reservation are to be on the property. No parties without approval prior to reservation. Any visitors are solely your responsibility. You also agree that you are solely responsible for the safekeeping of your personal belongings. In the unusual event of any damage you cause, you agree to pay for the entire repair.

WE ARE HERE TO HELP: I’m happy to answer any questions you may have and to help you in any way prior to or during your visit to assure your stay is most enjoyable. Be in touch any time.

WINTER VISITORS: Please be aware that we have a petite well-behaved seal point Birman cat who lives with us here typically January/February, though our home is available for guests throughout the entire year. (When guests are here we live in Rockport, the town next door. )You'll find the house super clean, but if you have severe cat allergies, please be aware of this and do what works for you.

Welcome to Gloucester!
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

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Children

Children allowed: ages 0-17

Glass tables, hardwood floors, oriental rugs.

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Events

No events allowed

Talk w/ owner re. small special events

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Pets

No pets allowed

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Smoking

Smoking is not permitted

No smoking of any kind in or on the property.

Important information

You need to know

Property Registration Number C0109621070
Property # 192597ha
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
Note from host: Talk w/ owner re. small special events
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, a first aid kit, and a deadbolt lock
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

About the neighborhood

Gloucester

Located near the beach, this vacation home is in Downtown Gloucester, a neighborhood in Gloucester. Schooner Adventure and Cape Ann Museum are cultural highlights, and some of the area's attractions include Maritime Gloucester and Rocky Neck Art Colony. Essex Shipbuilding Museum and Cogswell's Grant are also worth visiting. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with horse riding and cycling.
Map
Gloucester, MA

What's nearby

  • Schooner Adventure - 2 min walk - 0.2 km
  • Capt Bill & Sons Whale Watch - 8 min walk - 0.7 km
  • Cape Ann Museum - 8 min walk - 0.7 km
  • Maritime Gloucester - 10 min walk - 0.9 km
  • Pavilion Beach - 16 min walk - 1.4 km

Getting around

  • Gloucester Station - 15 min walk
  • Beverly, MA (BVY-Beverly Municipal) - 22 min drive

Restaurants

  • ‪McDonald's - ‬15 min walk
  • ‪Chipotle Mexican Grill - ‬3 min drive
  • ‪The Lobster of Gloucester - ‬15 min walk
  • ‪Seaport Grille - ‬4 min walk
  • ‪Dunkin' - ‬7 min walk

Frequently asked questions

Is WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC?

As of Sep 19, 2026, prices found for a 1-night stay for 2 adults at WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC on Oct 4, 2026 start from $538, 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?

Onsite parking is available at the property.

What time is check-in at WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC?

Check-in begins at 3:00 PM.

What time is check-out at WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC?

Check-out is at 11:00 AM.

Where is WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC located?

Located in Downtown Gloucester, this vacation home is within a 10-minute walk of Schooner Adventure, Cape Ann Museum, and Capt Bill & Sons Whale Watch. Maritime Gloucester and Cape Ann Historical Museum are also within 15 minutes. Gloucester Station is 15 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 144 out of 151 reviews
Rating 8 - Good. 6 out of 151 reviews
Rating 6 - Okay. 1 out of 151 reviews
Rating 4 - Poor. 0 out of 151 reviews
Rating 2 - Terrible. 0 out of 151 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home is a great location. Easy walking distance to everything in town. We loved it.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, location
Fantastic place, fantastic host
Stayed 10 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Home, well maintained. Communication throughout was excellent! We really enjoyed our stay.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Certainly, met our needs and more.
Stayed 8 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house in a great location in Gloucester. Plenty of space to read, socialize, or look toward the harbor. Good setup for cooking and dining. Our whole party really loved the space. Host was very helpful and responsive.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was impeccable and just amazing and better than described
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

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

Beautiful place with a great view of the water.

Excellent restaurants close by.
Stayed 6 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views and very comfortable home
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was beautiful and the view was fantastic!
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was easily accessed with the train Boston, Salem, Rockport, etc. Train station was 5 minutes away. Places to eat were close as well. So enjoyable!
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our visit to 21 Friend was outstanding as usual. We are repeat customers for this location for numerous reasons. The first reason is the hostess. Kathy is a true professional in what she provides as a hostess to every guest. She is easy to contact and willing to assist you in any way possible, The next positive factor is the amenties 21 Friend provides. I have rented Vrbo units worldwide and I have never seen a location exceeds the features/supplies and household items offered in 21 Friend street. As an example where have you found a grand piano in a rental unit - one is here. The kitchen is fully equipped with the basic essentials and Kathy has added bonus items such as a trash compacture, two ovens, and a cord of fire wood for the fireplace. Additionally, if you need something, just ask Kathy and she will probably find it somewhere in the house. Another important factor for choosing this location is the excellent cleaning aspects of 21 Friend st. After the cleaning service completes their work, Kathy followups with love and attention to every detail. Finally, the view from 21 Friend of the Gloucester Harbor is beautiful and every attraction the city has to offer is within a 10 minute drive. This is a great location to visit and my family and I look forward to every visit. p.s. we are already booked for 2027. Thanks Kathy
Stayed 8 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this home! Owner was quick to respond to all questions, super helpful, informative and friendly. Clean, full of light and we really loved the sun porch overlooking harbor. We will definitely be back!
Harbor view
Sunroom
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Amazing Stay in Gloucester

Stunning place, fantastic host. Highly recommend.
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

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

Perfect location

We had the best time in Gloucester staying at Kathy’s home. The location is perfect and even walking distance to restaurants and the downtown area. We also really enjoyed the great view from the front room. We had an unforgettable stay!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We hsd a very comfortable 5 night stay. Great neighborhood, with an easy walk to town. Loved the sunroom and living area off of the kitchen, as well as the Master suite. I also really appreciated the garage, having a rental car. Kathy checked in regularly and left good instructions for everything. Highly recommend.
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

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

Gloucester Vacation

The house was great and more room then we needed but better to much than not enough. The beds were so comfy.
Stayed 6 nights in Jul 2024
Verified review

10/10 Excellent

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

Excellent rental .. highly reccommend!

An extremely comfortable place to stay! Kathy is a GREAT host and the property is close to everything! So much to do in the area, I would definitely return. Best, Kate
Stayed 4 nights in May 2021
Verified review

10/10 Excellent

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

The home better than expected, and the perfect host!

This home could not have been more perfect for our visit to Gloucester! We were four retired siblings meeting up for some special time together. The sunroom was the icing of the cake. I would definitely consider staying here again.
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

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

Beautiful stay in downtown Gloucester

We had a wonderful time here. The house is beautiful, comfortable, spacious, and incredibly designed. The location couldn't have been more perfect. And Kathy was a kind and attentive host.
Stayed 4 nights in Dec 2022
Verified review

10/10 Excellent

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

The perfect getaway

The home and location was everything we were hoping for and more. Host was helpful, communicative, and kind. Our whole family had an incredible time and were sad to leave!
Stayed 5 nights in Jun 2023
Verified review

10/10 Excellent

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

fabulous

this location was a luxury retreat with views over looking the water- our hostess went above and beyond to make our stay spectacular!
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

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

Great stay

A beautiful home with great views and a super location with in walking distance of downtown GLO. Great communications with owner. Thanks.
Stayed 4 nights in Feb 2024
Verified review

10/10 Excellent

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

Beautiful Home

This was such a beautiful home and an ideal location for our trip. Kathy was a great host, providing lots of great recommendations for restaurants and activities. I’m already thinking about when I can come back with my husband.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

Absolutely beautiful stay!

Me and my friends had the best time at Kathy’s beautiful home, she was absolutely amazing!! She left us a list of fun things to do as well as emailed us an interesting boat tour we ended up going on & lucked out getting the entire yacht :) it was literally a dream vacation thanks to all of her suggestions I would definitely come back and stay here when I visit again.
Stayed 5 nights in Oct 2023
Verified review

10/10 Excellent

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

Gloucester stay

Kathy is a fantastic owner. Sweet, attentive to any needs. We loved our stay, my best friend and my daughter felt right at home. We’ll be contacting Kathy again for future stays
Stayed 6 nights in Oct 2024

About the host

Hosted by Kathy Eckles

Host profile image

I love welcoming guests to our home! I grew up outside of Cleveland and have lived on Cape Ann since 1997 when I purchased this home. My first career was as a senior executive in the retail industry for 24 years. I now provide psychology, coaching and​ group facilitation services for private individuals and business, civic, and religious leaders.

Why they chose this property

Cape Ann is inspiring. I love the sea, huge rocks, and rugged, genuine people. Once I knew I wanted to move here, I had a dream in which I saw the exact same view we have overlooking the inner harbor, so the moment I walked into this home, I knew I was in the right place.

What makes this property unique

Especially love the entire back of the house - kitchen, family room, sunroom, outdoor porch and master bedroom. As they all overlook the inner harbor, there's a peaceful sense of being steeped in the vibrant blend of beauty and everyday life. Guests also tell us they enjoy that we are an easy walk to the harbor, schooner sailing, the whale watch boat, downtown Gloucester restaurants and fun shops, and Cape Ann Museum.

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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