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

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A balcony with a table set for a meal, a vase of flowers, and a view of boats at sunset.
Beach nearby, sun loungers, beach towels
Interior
Smart TV, DVD player, books, video library
A living room with a TV, seating, a balcony with a view, and a dining area.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 41100 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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 (BOS-Logan Intl.)
    ‪62 min drive‬

Room options

About the neighborhood

Gloucester

Located in East Gloucester within a short walk of Massachusetts Bay, this vacation home is within a mile (2 km) of Good Harbor Beach. The vacation home includes a kitchen, a patio, and a dining area.
View more Vacation Homes in GloucesterOpens in a new window

What's nearby

  • Good Harbor Beach - 18 min walk - 1.0 mile
  • Cape Ann Museum - 2 min drive - 0.9 miles
  • Maritime Gloucester - 3 min drive - 1.2 miles
  • Capt Bill & Sons Whale Watch - 3 min drive - 1.2 miles
  • Niles Beach - 3 min drive - 1.8 miles

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms and a dining area. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washer/dryer, a coffee maker, and an ironing board.

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Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Limited onsite parking (max 1 space)

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Video library

Outdoor areas

  • Garden
  • Gas grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washer/dryer

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 7 steps to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator (single-level property)
  • Single level property
  • Smoking not allowed
  • Note from host: outside smoking only

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In a village
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Golf
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Double-glazed windows
  • Energy-saving switches in guestrooms
  • Garden
  • Unit size: 1,100 square feet
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 30

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Gather used towels
Remove personal items and take out the trash
Turn off the lights
Place used towels in tub
Failure to complete these may result in a negative review from the host.

Rules

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.

Pets

  • This property doesn't allow pets

Children and extra beds

  • Note from host: Children over 13 yrs. (including any visitors)

Events

No events allowed
Absolutely no partying. Quiet neighborhood.

Smoking

Smoking is not permitted
Outside smoking only

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
Onsite parties or group events are strictly prohibited
Note from host: Absolutely no partying. Quiet neighborhood.
Long-term renters welcome
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 and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 30
Property Registration Number 0033061070

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Note from host: Absolutely no partying. Quiet neighborhood.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.

Property is also known as

Romantic Summerwind Cottage Scenic Harbor View W/large Deck
Romantic Summerwind Cottage Scenic Harbor View W/large Deck
Romantic Summerwind Cottage Scenic Harbor View W/large Deck
Romantic “Summerwind Cottage” Scenic Harbor View w/Large Deck
Aug 1 8 Open! Romantic Cottage Scenic Harbor View W/large Deck
Aug 29 sep 4! Romantic Cottage Scenic Harbor View W/large Deck

Frequently asked questions

What can I see close to this vacation home?

This vacation home is situated in East Gloucester within a short 16-minute walk of Good Harbor Beach and also 19 minutes on foot from Rocky Neck Art Colony. You'll also find Massachusetts Bay and Schooner Adventure less than a mile away.

Is there parking available at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Yes, though there is a max of 1 space. You'll find a max of limited parking spaces.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What amenities will couples enjoy at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Amenities that appeal to couples at this historic vacation home include a kitchen and meal delivery service in each house, and some feature ocean view.

Are there hot tubs at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

No, there isn't a spa tub at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

No, this vacation home doesn't feature connecting guestrooms.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Beverly, MA (BVY-Beverly Municipal), which is 16.7 mi away (22 minutes by car). Another top airport is Lawrence, MA (LWM-Lawrence Municipal), which is around 25.1 mi away.

Are there rooms with balconies at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Yes, every house at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck comes with a patio and some offer ocean views.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 128 out of 135 reviews
Rating 8 - Good. 7 out of 135 reviews
Rating 6 - Okay. 0 out of 135 reviews
Rating 4 - Poor. 0 out of 135 reviews
Rating 2 - Terrible. 0 out of 135 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

9.0/10

Property conditions & facilities

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
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

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

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
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

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
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
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
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
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 traveler

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
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
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
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
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
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
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
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
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