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Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

Photo gallery for Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

A dining area with a wooden table, chairs, a bench with cushions, a wall-mounted painting, a decorative cabinet with plates, and a chandelier.
A balcony with a table set for a meal, a vase of flowers, and a view of boats at sunset.
A white wooden structure with a zigzag pattern, a staircase, and flower boxes.
A wooden deck with a mailbox, a table with chairs, and a view of the city.
A marina with boats docked, a waterfront view, and a town in the background.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.
  • Laundry made easy
    One of the few properties with an in-unit washing machine and dryer.
  • Walkable and wonderful
    Guests love the walkable location for its easy access on foot.
  • Discover nearby landmarks
    Walk to Good Harbor Beach
2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer/dryer
  • Air-conditioning
  • Barbecue
  • Deck or patio

Explore the area

View map
Gloucester, MA
  • Place, Good Harbor Beach
    ‪18 min walk‬
  • Place, Maritime Gloucester
    ‪3 min drive‬
  • Place, Niles Beach
    ‪3 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪62 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Living Room 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Spaces

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

About this property

Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck

Welcome to Summerwind Cottage! Wake up to harbor views, enjoy coffee or sunset cocktails on a spacious private deck, and walk everywhere from this bright, coastal retreat in the heart of Gloucester.

This thoughtfully furnished two-bedroom home offers a relaxed seaside feel with comfortable living spaces, natural light, and a large deck overlooking the harbor — a guest favorite for dining, lounging, and taking in the view. Located just minutes from downtown Gloucester, you can easily walk to restaurants, shops, galleries, and the waterfront, with beaches only a short drive away.

The home sleeps up to five guests comfortably with two bedrooms and a full sofa bed, making it ideal for couples, friends, or a small family looking for a peaceful coastal getaway. Two off-street parking spaces are included — a rare and valuable amenity in this location.

Whether you’re here for summer beach days, fall foliage, arts and culture, or a relaxing coastal escape, this home offers the perfect balance of convenience, comfort, and calm.

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10.0 out of 10, Exceptional, (47 reviews)
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House Rules

Check in after 3:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 13–17
Children over 13 yrs. (including any visitors)
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Events

No events allowed
Absolutely no partying. Quiet neighborhood.
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Outside smoking only

Check-out instructions

The host requires you to complete the following before checking out:
Gather used towels
Remove personal items and take out the rubbish
Turn off the lights
Place used towels in tub
Failure to complete these may result in a negative review from the host.
Maximum Stay: 14 Nights Absolutely not a party house. Please take conversation inside after 10pm.
CLOSE UMBRELLAS when not in use. Refrain from using grill on windy days.

Important information

You need to know

Property Registration Number 0033061070
Property # 953745
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: Absolutely no partying. Quiet neighborhood.
Long-term renters welcome
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 first aid kit

About the area

Gloucester

Located on the waterfront, this holiday home is in East Gloucester, a neighbourhood in Gloucester. Travellers eager for a bit of culture can stop by Hammond Castle, while those wishing to experience the area's natural beauty can explore Good Harbor Beach and Cape Ann. Schooner Adventure and Rocky Neck Art Colony are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.
View more Holiday homes in GloucesterOpens in a new window
Map
Gloucester, MA

What's nearby

  • Good Harbor Beach - 18 min walk - 1.5 km
  • Maritime Gloucester - 3 min drive - 1.8 km
  • Capt Bill & Sons Whale Watch - 3 min drive - 1.8 km
  • Rocky Neck Art Colony - 3 min drive - 2.2 km
  • Niles Beach - 3 min drive - 2.9 km

Getting around

  • Gloucester Station - 8 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 22 min drive

Restaurants

  • ‪Dunkin' - ‬18 min walk
  • ‪Dunkin' - ‬2 min drive
  • ‪The Lobster of Gloucester - ‬3 min walk
  • ‪The Burn Tavern - ‬19 min walk
  • ‪Seaport Grille - ‬16 min walk

Frequently asked questions

Is Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck pet-friendly?

No, pets are not allowed at this property.

How much is parking at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

On-site parking is available at the property.

What time is check-in at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Check-in begins at 3:00 PM.

What time is check-out at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Checkout is at 10:00 AM.

Where is Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck located?

Located in East Gloucester, this holiday home is within 1 mi (2 km) of Massachusetts Bay and Good Harbor Beach. Schooner Adventure and Rocky Neck Art Colony are also within 1 mile (2 km). Gloucester Station is 30 minutes by foot.

Reviews

10

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. 129 out of 136 reviews
Rating 8 - Good. 7 out of 136 reviews
Rating 6 - Okay. 0 out of 136 reviews
Rating 4 - Poor. 0 out of 136 reviews
Rating 2 - Terrible. 0 out of 136 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

9.0/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Cassie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time! Linda the host was awesome super friendly! The house was beautiful, same with the town!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place to stay with everything you’d need plus the warmest and most accommodating hosts! Convenient to commute to Salem and come back for lobsters on the water and a walk back to the rental.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 14 October 2025
So glad you enjoyed your stay, we hope you'll be back one day!
Verified

10/10 Excellent

Laura B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at the cottage. Overall location was easy to get in and out of town as we explored different parts of MA.
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Glenda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Properly was very well kept and comfortable. Host was very nice and accommodating. We had a great time.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Kara H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage is lovely, spacious and nicely appointed. Great view of the harbor. The hosts were helpful and welcoming.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Christina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This seaside cottage was perfect. The kitchen was well stocked with pots/pans, condiments, and coffee necessities. Everything was very clean, well kept, and comfortable. The host was quick to communicate and was very invested in making our stay the best it could be. The driveway is challenging to enter/exit but not unusual for the area - just take your time and have a spotter!
Stayed 3 nights in Oct 2025
Response from VrboOwner on 14 October 2025
Thanks so much for the lovely review, it's so important to hear feedback. We are always working toward providing a more user-friendly parking spot (tough when we are located on a dead-end lane.) Hope to remedy this soonest with a new landscape design, making for an easier turnaround. Thanks again!
Verified

10/10 Excellent

Anna F.

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

Great Location and Peaceful Stay

Great Hospitality from the Hosts. Quiet.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

cmcdanie74

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

Beautiful cottage on the bay

We were really impressed with Summerwind cottage, it was beautifully decorated, and comfortable. Linda gave us great recommendation on what to do/see in the area. We can't wait to visit again.
Stayed 4 nights in Oct 2023
Archival

8/10 Good

Kim M.

Great house

This was a great place to stay. Nice and quiet with all the amenities needed. The owner is very nice as well! We would rent again.
Stayed 4 nights in Sep 2017
Response from VrboOwner on 2 August 2023
Thank you for your kind words, we always strive to create the best possible environment for our guests (our "suggestions" form is a great way to let us know if we need to make any improvements... assuring a 5 star stay for our guests). Would love your personal feedback. Thanks again for your booking, we welcome you back in the future!
Verified

10/10 Excellent

Anne S.

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

Nice experience

The cottage is as advertised. So much care went into the art on the walls and the whole main room. It is a beautiful site. The kitchen had everything we needed. The patio was a joy as well. We enjoyed many of the restaurants that seem very close by
Stayed 12 nights in Jun 2025
Verified

10/10 Excellent

Sissy H.

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

Great location, very comfortable.

Great experience! Highly recommend
Stayed 4 nights in Jun 2021
Response from VrboOwner on 2 August 2023
So happy to hear you enjoyed the space/area! Thank you.
Verified

10/10 Excellent

Kristin A.

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

Beautiful location

We couldn’t have been happier with our stay!! We had a family wedding & this was the perfect place to stay!! The porch offers a gorgeous view of the harbor & we look forward to returning to explore the area. Linda is a wonderful host & super welcoming!!
Stayed 4 nights in Sep 2023
Response from VrboOwner on 23 September 2023
Enjoyed meeting you folks and having a few laughs! Hope the wedding was magical... please come back whn you can relax a bit more, lol!
Verified

10/10 Excellent

Regina B.

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

Wonderful Vacation Spot

Our stay was great. Linda was a perfect host - nearby if needed but gave us our privacy. The house was lovely and just as depicted. Lots of things to do - many within walking distance. Hope to return!
Stayed 7 nights in Jun 2019
Response from VrboOwner on 2 August 2023
Wonderful guests, left the studio very clean and would welcome them back anytime.
Verified

10/10 Excellent

Kristin E.

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

Gloucester Getaway

Another fabulous stay that did not disappoint! Linda and Hank are attentive and enthusiastic hosts who have dedicated themselves to making our stay outstanding!!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Verified traveller

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

Loved it!

Great location, easy check in charming home with great views. Loved being on the deck to watch the sunset!
Stayed 3 nights in May 2022
Response from VrboOwner on 2 August 2023
Thanks, Linda - so glad you enjoyed your stay!
Verified

10/10 Excellent

Daniel T.

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

30th Anniversary

Beautiful and peaceful!!!! And the owner was absolutely incredible,
Stayed 4 nights in Oct 2024
Response from VrboOwner on 1 November 2024
Thanks for the high praise, Dan!!! So glad you enjoyed your stay.
Verified

10/10 Excellent

Jason I.

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

Wonderful area / Cozy Stay

We had a great stay at in Gloucester. The house was very clean and well taken care of. The town and beaches were great. It was perfect for our family getaway. Linda was great and easy to communicate with. We would highly recommend the trip.
Stayed 7 nights in Jul 2020
Response from VrboOwner on 2 August 2023
Thanks, Jason - A pleasure to host you all!
Verified

10/10 Excellent

Anita C.

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

Cute little cottage

Linda was a great host —she gave us lots of helpful tips on things to do and see. The cottage is cozy: Comfortable bed and great water pressure in the shower. Thanks for a great stay.
Stayed 7 nights in Jun 2019
Response from VrboOwner on 2 August 2023
It was a pleasure to host this lovely, quiet couple - cottage was left in very clean, orderly state. Definitely recommend renting to them.
Verified

10/10 Excellent

Jim O.

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

Wonderful Vacation Get-A-Way

We spent a week touring Cape Ann and this property was a perfect location for our vacation. House was clean, very well appointed, comfortable, and located with a beautiful view of the Harbor from the outdoor deck and from inside. This was a perfect location base camp for daily excursions all over Cape Ann and Cape Cod. We enjoyed this house and highly recommend this property.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Holly K.

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

Great place!

A great, comfortable & clean place. Very convenient to lots of restaurants and day trips to places like Rockport and Newburyport. Near lots of beaches and scenic drives. Owner is terrific, very accommodating and nice. Definitely recommend it.
Stayed 4 nights in May 2021
Response from VrboOwner on 2 August 2023
These two folks were a delight to host (along with their adorable, well-behaved dog.) They left the cottage in great shape and we would welcome them back anytime. Highly recommend as great guests!
Archival

10/10 Excellent

judy f.

Perfect location...Perfect house!

My husband and I spent the week of the 4th in Gloucester..the house was perfect! So tastefully done and Linda thought of everything to make our stay comfortable! Gloucester is such a pretty area with lots of area's to explore!I would highly recommend this home and area for a great vacation.
Stayed 7 nights in Jul 2016
Response from VrboOwner on 2 August 2023
Thank you for your wonderful review, we are so pleased to hear that you enjoyed the house and decor - and had everything you needed. You were great guests and we hope you'll be back to stay in the future! Linda and Hank
Verified

10/10 Excellent

Amanda A.

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

Cute cottage with a View

We were there for a long, adults-only weekend to visit Salem and this cottage did not disappoint. Cottage is exactly as described and the owner Linda was very friendly, pleasant, and helpful! Can't wait to be back for another trip.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 3 November 2023
Thank you Amanda, "We aim to please", lol. Hope to host you again someday!
Verified

10/10 Excellent

Sherry K.

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

Vermont Gang

We truly enjoyed our week in Gloucester. All of the suggestions about where to eat and places to visit. Our favorite beach was Long Beach and our favorite activity was the sunset schooner sail. We will definitely stay here again!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Glenda B.

Lovely 2 Bedroom home. The owners put so much thought into making this an exceptional place to stay!

We could not have been more pleased with this VRBO- about the best we have ever stayed at! The owners put so much thought into making this home beautiful and comfortable and were so pleasant to work with! Loved the deck overlooking Gloucester harbor! Very well stocked home and very comfortable beds! Will definitely be staying here again!
Stayed 7 nights in Jun 2018
Response from VrboOwner on 2 August 2023
Thank you, Glenda - we enjoyed hosting you and are very pleased that you enjoyed the cottage. Much appreciated!
Verified

10/10 Excellent

Jill J.

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

My husband and I and two old friends spent 4 nights at this beautiful quiet cottage overlooking the

We had a wonderful time at this cottage over looking the port from a spacious deck. The cottage was spotless clean and accommodating. Linda the owner was next door and very nice. We'd return anytime.
Stayed 4 nights in May 2023

About the host

Hosted by Linda Amero, Owner

Host profile image
We love making our guests feel right at home and are always happy to help ensure a comfortable, memorable stay. Hank and I grew up on Cape Ann and have lived in Gloucester most of our lives—we wouldn’t have it any other way. We live right next door, so help is close by if needed, while always respecting your privacy.

Linda is a musician and artist, and Hank is a retired woodworker and lifelong rock-and-roll fan with plenty of great stories. We delight in sharing local tips on Gloucester and nearby Salem, just a short drive away—especially popular in the fall.

Why they chose this property

Summerwind Cottage offers an unbeatable location. Just minutes from Good Harbor, Long Beach, and Niles Beach (about 5 minutes by car in either direction), with downtown Gloucester, Rocky Neck Art Colony, and waterfront dining close by. Rockport is only 7 minutes away, the Boston train is across town, and Salem is an easy 20 minutes by car or train. Enjoy a quiet setting that’s still right in the middle of it all.

What makes this property unique

Open living space and lovely large deck with scenic harbor view - facing west for viewing of our magnificent sunsets. 15 walk to Good Harbor Beach footbridge (Gloucester's crown jewel.) Close to all the restaurants. Quiet neighborhood yet very close and convenient to all activities.

Languages:

English

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