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

Photo gallery for Romantic Summerwind Cottage-Gloucester Harbor View 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 dining table set with blue napkins and a vase of flowers, overlooking a marina with boats and buildings.
A table set for a meal with a view of boats and a sunset.
A white wooden structure with a zigzag pattern, a staircase, and flower boxes.
A two-story house with a front porch, a wooden deck, and a staircase leading to the upper level.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
Perched along the water, this 2-bedroom vacation home accommodates 5 guests with 1 bathroom. It features 1 separate living room and offers access to games. Enjoy activities like fishing, mountain biking, and swimming nearby, while the outdoor spaces include a patio, porch, and deck with water views. Visit attractions like Schooner Adventure and The Gorton Theatre.

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.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Good Harbor Beach
2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Porch or lanai
  • Gas barbecue
  • Washer/dryer
  • Onsite parking available
  • Air-conditioning
  • Internet access

Explore the area

View in a 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 (BNH-Boston Harbor Seaplane Base)
    ‪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 · Bathtub · Toilet · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Number of living rooms
Garden
Dining area

About this property

Romantic Summerwind Cottage-Gloucester Harbor View 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.

Guest Safety and Age Policy: Due to specific architectural hazards—including an elevated 15-foot deck and steep cellar stairs accessible from the kitchen—this property is not safe or suitable for toddlers or young children. We strictly limit bookings to adults and children aged 10 and over.

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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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 10 yrs. + welcome (incl. 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 AWNING and UMBRELLAS when not in use. Refrain from using grill on windy days.
We strictly limit bookings to ages 10 + for safety due to specific fall hazards (elevated 15' deck and steep cellar stairs with bi-fold door off kit.)

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. The Gorton Theatre and Schooner Adventure are cultural highlights, and some of the area's attractions include Rocky Neck Art Colony and Maritime Gloucester. Essex Shipbuilding Museum and Cogswell's Grant are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with mountain biking and hiking.
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
  • Cape Ann Museum - 2 min drive - 1.5 km
  • Maritime Gloucester - 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
  • ‪The Lobster of Gloucester - ‬3 min walk
  • ‪Seaport Grille - ‬16 min walk
  • ‪Dunkin' - ‬2 min drive
  • ‪The Burn Tavern - ‬19 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Romantic Summerwind Cottage-Gloucester Harbor View w/Large Private Deck?

As of 12 Oct, 2026, prices found for a 1-night stay for 2 adults at Romantic Summerwind Cottage-Gloucester Harbor View w/Large Private Deck on 10 May, 2027 start from S$1,651, 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 Romantic Summerwind Cottage-Gloucester Harbor View w/Large Private Deck?

On-site parking is available at the property.

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

Check-in begins at 3:00 PM.

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

Checkout is at 10:00 AM.

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

Located in East Gloucester, this holiday home is within a 15-minute walk of Massachusetts Bay and The Gorton Theatre. Schooner Adventure and Good Harbor Beach 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. 130 out of 137 reviews
Rating 8 - Good. 7 out of 137 reviews
Rating 6 - Okay. 0 out of 137 reviews
Rating 4 - Poor. 0 out of 137 reviews
Rating 2 - Terrible. 0 out of 137 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place was perfect - clean, well-equipped, charming and exactly as described. Linda as host was also wonderful! We’ve visited Gloucester for decades and this was one of the best rentals we’ve ever had. Hats off to Linda and Hank. We had the best week and look forward to returning!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 Oct, 2025
So glad you enjoyed your stay, we hope you'll be back one day!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Archival

8/10 Good

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 Aug, 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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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 Aug, 2023
So happy to hear you enjoyed the space/area! Thank you.
Verified review

10/10 Excellent

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 Sept, 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 review

10/10 Excellent

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 Aug, 2023
Wonderful guests, left the studio very clean and would welcome them back anytime.
Verified review

10/10 Excellent

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 Aug, 2023
Thanks, Linda - so glad you enjoyed your stay!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 Aug, 2023
Thanks, Jason - A pleasure to host you all!
Verified review

10/10 Excellent

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 Oct, 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 review

10/10 Excellent

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 Aug, 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 review

10/10 Excellent

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 Nov, 2024
Thanks for the high praise, Dan!!! So glad you enjoyed your stay.
Verified review

10/10 Excellent

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
Archival

10/10 Excellent

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 Aug, 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 review

10/10 Excellent

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 review

10/10 Excellent

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 Nov, 2023
Thank you Amanda, "We aim to please", lol. Hope to host you again someday!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

Picturesque Cottage

This cottage was beyond cute. Loved the decor and everything you could want was provided. Met the hosts and they were so friendly and accommodating. A real gem!!
Stayed 3 nights in Sep 2021
Response from VrboOwner on 2 Aug, 2023
Lovely, quiet couple. They left the house spotless and I would welcome them back anytime. Highly recommend as wonderful guests.
Verified review

10/10 Excellent

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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