Apartment

Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach

Photo gallery for Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach

A harbor with a sailboat docked, a stone breakwater, and houses in the background.
A cozy living room with exposed wooden beams, a brown leather sofa, a beige armchair, and a wooden coffee table.
A room with a wooden table, chairs, a red door, and large windows.
A small ice cream store with a red door and a sign that reads "The Ice Cream Store."
A garden with yellow flowers and trees.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Top-rated comfy beds
    Guests liked the comfy beds here.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Front Beach
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Balcony or patio
  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Non-smoking
  • Microwave

Explore the area

View in a map
ROCKPORT, MA
  • Place, Motif No 1
    ‪2 min walk‬
  • Place, Shalin Liu Performance Center
    ‪5 min walk‬
  • Place, Front Beach
    ‪8 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪69 min drive‬

Where you'll sleep

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach

Stay just steps from Rockport’s beautiful beaches, charming shops, and local dining in this inviting coastal retreat. Captain’s Quarters blends classic seaside charm with modern comfort, creating the perfect home base for couples or small families seeking a relaxing North Shore escape.



Wake up and stroll to Front Beach for a morning swim, explore Bearskin Neck’s art galleries and boutiques, or enjoy fresh seafood by the harbor — all within easy walking distance. After a day by the ocean, return to unwind in a peaceful setting designed for comfort and convenience.



Inside, you’ll find a bright and welcoming living space, a fully equipped kitchen for preparing meals, and thoughtfully appointed bedrooms designed for restful nights. Whether you’re here for a beach getaway, a romantic weekend, or a quiet coastal recharge, Captain’s Quarters offers everything you need for a stress-free stay.



Guests love the unbeatable walkable location and relaxed seaside atmosphere. Park once and enjoy Rockport entirely on foot.

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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
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Events

No events allowed
Quiet hours begin at 9PM. Strict.
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Pets

No pets allowed
No pets
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Smoking

Smoking is not permitted
Guest is required to sign a Rental Agreement. Security Deposit Required of $195. A cancellation fee applies.
Minimum age to rent is 25. NO Smoking. NO pets. NO parties/events. NO outside guests. Infants are counted as guests.
No Smoking, Pets, or extra guests shall be fined from security deposit at owners discretion.

Important information

You need to know

Property Registration Number C0161352520
Property # 1296558vb
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
Note from host: Quiet hours begin at 9PM. Strict.
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 and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Rockport

Located in Rockport, this apartment is in the city centre and near the beach. Motif No 1 and Paper House are local landmarks, and some of the area's attractions include Schooner Adventure and Maritime Gloucester. Rocky Neck Art Colony and Essex Shipbuilding Museum are also worth visiting. Kayaking, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Apartments in RockportOpens in a new window
Map
ROCKPORT, MA

What's nearby

  • Bradley Wharf - 2 min walk - 0.2 km
  • Motif No 1 - 2 min walk - 0.2 km
  • Rockport Art Association & Museum - 3 min walk - 0.3 km
  • Shalin Liu Performance Center - 5 min walk - 0.5 km
  • Front Beach - 8 min walk - 0.7 km

Getting around

  • Rockport Station - 15 min walk
  • Beverly, MA (BVY-Beverly Municipal) - 27 min drive

Restaurants

  • ‪Chipotle Mexican Grill - ‬8 min drive
  • ‪Dunkin' - ‬6 min drive
  • ‪Surfside Subs - ‬7 min drive
  • ‪Common Crow Natural Market - ‬5 min drive
  • ‪Long Beach Dairy Maid - ‬7 min drive

Frequently asked questions

Is Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach?

As of 6 Oct, 2026, prices found for a 1-night stay for 2 adults at Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach on 8 Nov, 2026 start from S$984, 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 Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach?

On-site parking is available at the property.

What time is check-in at Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach?

Check-in begins at 3:00 PM.

What time is check-out at Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach?

Checkout is at 11:00 AM.

Where is Filing Site of Widows Bay! Rockport Coastal Retreat Walk To Beach located?

Located in the heart of Rockport, this apartment building is steps away from Bradley Wharf, Motif No 1 and T Wharf. Rockport Art Association & Museum and Shalin Liu Performance Center are also within 5 minutes. Rockport Station is 15 minutes by foot.

Reviews

9.4

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. 33 out of 44 reviews
Rating 8 - Good. 8 out of 44 reviews
Rating 6 - Okay. 3 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

9.4/10

Cleanliness

10/10

Amenities

8.0/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful few days here with lots of great food and sites. Great location to visit and go Whale Watching.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fun place to stay in the middle of everything right downtown super cute vintage cottage would absolutely stay here again. Everything was in walking distance. Me and my wife had a lot of fun.
Stayed 3 nights in May 2026
Response from VrboOwner on 28 May, 2026
Thanks Gabe, so glad you enjoyed your visit!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I came back! I love this spot. It’s so full of coziness and character, and the views are picturesque. Our host Matt was super helpful and gracious. Very grateful for our stay!
Stayed 2 nights in Mar 2026
From a partner site

10/10 Excellent

Great Vacation Stay

Our family of three stayed at the Captain's Quarters for a week and it was a wonderful vacation. The location was surprisingly quiet and peaceful, yet central to everything. We had everything we needed in the apartment and beds were comfortable for us.
Verified review

10/10 Excellent

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

Cute place!

Really enjoyed the town and place!
Stayed 3 nights in Oct 2023
Response from VrboOwner on 23 Oct, 2023
Thanks for staying with us Jenna!
From a partner site

10/10 Excellent

Perfect!

Great charming place in a perfect location. Very clean and kitchen well stocked. Would def stay again.
From a partner site

10/10 Excellent

Amazing! Loved it

I had a great weekend getaway at Matt's place. Loved it and would definitely recommend/stay here again.
Verified review

10/10 Excellent

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

Captians Quarters

Had a great stay in the heart of Rockport's Bearskin Neck. Location is fantastic, walk to shops, restaurants, and beaches. Matt was a great host, very responsive to a couple of small issues that came up. Would definitely stay here again!
Stayed 13 nights in Apr 2025
Verified review

10/10 Excellent

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

Cute and Convenient

Great place to stay and very convenient to get to a lot of places easily.
Stayed 4 nights in Sep 2023
Verified review

8/10 Good

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

Getaway with a friend

Sweet, very comfortable lodging short term. Perfect street location off-season if looking for a quirky, quiet, historic spot with immediate access to beautiful Nature.
Stayed 2 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely beautiful place to stay! My kids already asked me if we can go back next year and stay in the same place. Everything was clean, the apartment is absolutely beautiful. The location is fantastic because it’s right down the street from a great beach and when you go out the door, you are right in the middle of all the beautiful little shops.My 15-year-old daughter thank me numerous times for bringing them there.
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place is in a great location for experiencing all the delights of Rockport. It’s cozy, well maintained, and nicely decorated. The stairs to the quarters are a little steep, but manageable. We had a wonderful time there.
Stayed 2 nights in May 2023
From a partner site

10/10 Excellent

Cozy village retreat

The nautical setting of the apartment added to our New England adventure. Hiking trails, local quarries, shops, and restaurants all within walking distance. Beautiful views of the sea and rocky terrain. Parking is inconvenient but doable. We were pleasantly surprised by the peacefulness at night considering we were staying in the middle of the village. Highly recommended for a couple looking for a weekend getaway.
Verified review

10/10 Excellent

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

Lovely Apt right in the action.

Lovely Apt right in the action.
Stayed 1 night in Apr 2024
Verified review

10/10 Excellent

Really cool place, great location

The house was clean, comfortable, and really easy to check in. Free parking was pretty easy to find if you’re willing to walk 5 minutes. Bearskin neck gets very busy with people during the day but is very quiet and peaceful at night. Would definitely stay here again.
Stayed 3 nights in Apr 2019
Response from VrboOwner on 3 Apr, 2020
Thanks for the nice review Brad! It was great having you as guests. We hope to see you again some day
Verified review

6/10 Okay

Liked: Cleanliness, communication
Nice location. Overall I’m satisfied, except parking is a challenge, especially for older adults, and the shower was extremely small and cramped. But we did enjoy our stay.
Stayed 3 nights in Jun 2024
Verified review

10/10 Excellent

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

By the sea

Lovely home located right by the water. Nestled amongst delicious restaurants, cozy cafes & local galleries/shops, close to grocery store & gas station. Clean & cozy.
Stayed 6 nights in Nov 2024
Verified review

10/10 Excellent

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

Sweet little spot in ideal Rockport Location

We have a toddler and a teenager. This afforded our youngest to nap between visiting beaches while our eldest could explore and keep busy.
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

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

Great location

If you like the charm of historic properties and being in the middle of it all, this is the property for you. Parking is offsite and typically a 4 min walk. We enjoyed being right on Bearskin Neck, close to shops, restaurants, coffee shops. Thanks Matt!
Stayed 5 nights in Sep 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy
My kids (10 and 12) and I really enjoyed staying here. The town is adorable and everything is within walking distance. The condo was easy to find and get into, with a cute view of the shops lining the street. The parking situation could be frustrating to some, but we live in a city without off-street parking so we’re used to it. The only day I chose to pay to park was when we went to the beach so I wouldn’t have to lug all of our stuff the whopping .3 miles lol. The rest of the time I parked for free on School street which was also .3 miles from the condo (opposite direction of the beach). There are a few things you should know before you go:•It’s a very old building and the floors are very wonky. Be careful if you aren’t sure footed, it kinda made me feel drunk.•The shower is so tiny! I’m 5’3/120 and it was tight for me, definitely couldn’t shave my legs in there.•The smell as soon as you enter the building is off putting, very old and musty, however the condo smells fine. I only say this because we drove 8 hours in the rain and traffic, and my first impression was “oh no”…. but it was all good once we got upstairs!All in all definitely worth the stay!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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

Absolutely wonderful!!

Bear skin neck is such a charming place!!! We came from Texas and I had no idea when booking just how quaint the town is with all of the shops! And this place is in the heart of the retail area in walking distance to everything. This was my favorite vacation stay ever! Would definitely recommend staying here. The photos of the place should be updated because the bedding and couches have been updated. Would definitely stay here again.
Stayed 2 nights in Oct 2023
From a partner site

10/10 Excellent

Most charming place in Rockport MA

I have stayed at many,many places in the country and this is by far my favorite spot! The Captains quarters is quaint and has so much charm and personality! It was clean and comfortable. We felt safe and it had a lot of privacy. The location was perfect too. We walked to all the shops and restaurants. We had great views! We will definitely come back or check out one of Matt’s other properties! I highly recommend Captains Quarters!!
From a partner site

10/10 Excellent

Super cute and great location

LOVED this stay! The Captain's Quarters was charming and lovely....it was well appointed with comfy linens and beds, enough towels for two people, super comfy couch and chair and just already full of charm. There are many quirks as it is a very old building (slanted floors, creaky doors, SMALL shower) but absolutely DELIGHTFUL! We loved the location - even though BSN was sleepy (it was a February stay) it was still lovely to walk to dinner, drinks, shopping...there was plenty open. The views and the location were just awesome. The owner was helpful and so quick to respond to any questions or needs. We will be back!
Verified review

10/10 Excellent

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

Wonderful Location!

Great place to stay! Tons of character and charm. Surrounded by restaurants, little shops, and history. Full kitchen, spacious bedrooms, and a wonderful little porch to gaze upon the sites. Bathroom is a bit small for the larger people out there, but we made it work just fine. Also, if you have any mobility issues, when I say that this place retains it's original character, it has uneven flooring and lots of little ridges which make it an adventure at night. These aren't knocks on the accommodations, just helpful advice. I highly recommend this location. Thanks for the wonderful experience!
Stayed 4 nights in Oct 2024
Verified review

8/10 Good

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

Right on Bearskin Neck but not on the main drag, quiet at night (mid May).

It was tricky to have to wait for the door to unlock itself and finding the place in the pouring rain at night didn't help (you can't hear the lock mechanism unlocking in the rain). The numbers on the outside of the house need clarification. Place very cute, very clean and comfortable except mattresses need an update.
Stayed 4 nights in May 2025

About the host

Hosted by Matt Walsh

Host profile image

Why they chose this property

Located in the heart of Bearskin Neck, Rockport’s famous artist colony, this rental is surrounded by local galleries, artisan shops, and charming waterfront restaurants. Step outside to enjoy fresh seafood, boutique shopping, and live music, or take a short stroll to scenic beaches and the Shalin Liu Performance Center.

What makes this property unique

• A historic building that was once The Sail Loft of Rockport • Exposed wooden beams and original stretcher hooks used for mending sails • Juliette-style balcony overlooking the heart of Bearskin Neck • Prime location with easy access to beaches, harbor views, and local attractions. No driveway.

Languages:

English

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