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Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester

Waterfront holiday home with kitchen and patio

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Beach nearby, sun-loungers, beach towels - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)
Marina - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)
Exterior detail - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)
Outdoor dining - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)
Smart TV, DVD player, books, video library - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)
Escape to the Summerwind Cottage and enjoy Gloucester harbor views from the spacious deck. With 2 queen beds, a twin air mattress, and charming decor, you'll unwind in style near Good Harbor and Niles beaches. You're just minutes away from downtown shopping and restaurants as well as Rocky Neck Art Colony galleries.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4102 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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About this property

Entire place

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

Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester

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.

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Limited on-site parking (max 1 space)

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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 lift (single-level property)
  • Single level property
  • Smoke-free property
  • Note from host: outside smoking only

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • In a village
  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • 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
  • Snorkelling 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

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Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are 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 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.

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

Pets not allowed

Children and extra beds

Children are welcome
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
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
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
Property Registration Number 0033061070

We should mention

A car is recommended for transport to and from this property

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

About the area

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 Maritime Gloucester and Essex Shipbuilding Museum. Cogswell's Grant and Long Hill are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching. Visit our Gloucester travel guide
View more Holiday homes in Gloucester
Map
Gloucester, MA

What's nearby

  • Good Harbor Beach featuring a sunset, a sandy beach and general coastal views
    Good Harbor Beach
    16 min walk - 1.4 km
  • Cape Ann Museum featuring art and interior views
    Cape Ann Museum
    2 min drive - 1.5 km
  • Maritime Gloucester as well as a small group of people
    Maritime Gloucester
    2 min drive - 1.8 km
  • Niles Beach featuring general coastal views, a bay or harbor and a beach
    Niles Beach
    2 min drive - 2.9 km
  • Capt Bill & Sons Whale Watch
    19 min walk - 1.7 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
  • Seaport Grille
    16 min walk
  • The Burn Tavern
    19 min walk
  • Source Bakery
    3 min drive

Frequently asked questions

Is Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester pet-friendly?

No, pets are not allowed at this property.

How much is parking at Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester?

On-site parking is available at the property.

What time is check-in at Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester?

Check-in begins at 3:00 PM.

What time is check-out at Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester?

Checkout is at 10:00 AM.

Where is Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester 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.

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Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

9.8

Location

10

Staff & service

9.0

Property conditions & facilities

Reviews

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

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

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

10/10 Excellent

Kristin A., Trumbull, CT

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

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

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

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

10/10 Excellent

Verified traveller

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

Ideal getaway!

We felt comfortable the moment we entered Summerwind Cottage. Everything about the property was well planned, executed, and maintained. We loved sitting on the deck watching the activity in the marina, eating our meals, and seeing the sunsets. Our host made sure we had everything we needed. And we were delighted when we found Good Harbor Beach on our morning walk.
Stayed 7 nights in Sep 2024

10/10 Excellent

Rute F.

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

Perfect!

We enjoyed our stay here. The house was clean and had everything we needed. Linda was very attentive to us and made sure we had everything we needed. Sunsets were memorable!
Stayed 7 nights in Aug 2023

10/10 Excellent

Nathalie D.

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

Great rental!

We loved the warm welcome we had from the owner, Linda. The house was clean and perfectly provisioned with everything we needed. We were well located to visit Boston (via train) and surrounding areas. We loved our stay! I highly recommend this home. Nathalie and friends (Canada & Switzerland)
Stayed 4 nights in Sep 2023

10/10 Excellent

John H.

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

Don’t miss this one!

Excellent! Exactly as described. Clean, comfortable, decorated, great shower! True home away from home. Linda has done all the work for you. All great recommendations!
Stayed 4 nights in Oct 2024

10/10 Excellent

sylvia g.

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

So fresh, so clean

This gem of a house had all the amenities that i need. The veiw was So Gorgeous, im already missing it. Also missing that fresh air, fresh fish. This was my first time to the east coast and im in love.
Stayed 3 nights in Oct 2024

10/10 Excellent

Brittany K.

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

Girls trip

Everything was perfect. The home was so clean and had everything we needed, even extras like coffee and creamer for mornings on the beautiful deck. The sunset was incredible in the evenings. Linda was so kind and even stopped by to see if we needed anything. The area is beautiful and you HAVE to try the Chicken Vodka Pasta from The Lobster which is just a short walk away (we had it twice in 2 days - that’s how good!).
Stayed 3 nights in Oct 2024

10/10 Excellent

Frederick M.

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

Gloucester cottage with harbor view

Great rental. Extremely well decorated, comfortable furniture, well equipped kitchen. Nice bright windows. Extremely clean and well maintained. Great deck set up with view of part of the harbor. Really good seafood takeout a 3-minute walk away. 5-minute drive to downtown; parking is tight but we got parking easily 1-2 short blocks off Main Street. Great seafood restaurants and a nice Italian section too. Definitely would return and definitely recommend this property.
Stayed 7 nights in Jun 2024

10/10 Excellent

Dusty S.

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

First Girls Trip

My best friend, her daughter, and I had our first girls trip to the charming cottage on the bay. The space was perfect for the three of us and had everything we needed for our trip. At the end of our days in Salem it was nice to sit out on the deck and watch the sunset. Linda provided exceptionally good communication and accommodations to our extra needs. We were sad to leave.
Stayed 3 nights in Sep 2023

10/10 Excellent

Joseph J.

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

A Little Bit of East Coast Paradise

My husband and I chose this VRBO as a getaway treat to celebrate our upcoming 50th wedding anniversary, and it delivered four days and five nights of splendid relaxation. The accommodations more than met our expectations, and we were able to forget about our troubles and enjoy each others company and our surroundings without any fear of being disappointed. Even the weather cooperated and allowed us to enjoy the balcony/deck in the evenings while taking in the blue water and colorful fishing vessels in the harbor. The proximity to excellent dining was another perk. Although we have visited Gloucester four times in the past, we discovered a few new haunts which offered the freshest and most delicious seafood to be found just about anywhere on the eastern seaboard, and we have tried many over the years. One restaurant and another purveyor of fresh seafood were within walking distance. Here are a few items that we truly appreciated: 1. Tasteful and comfortable decor. 2. Delightful artwork throughout. 3. A well-appointed kitchen with a Keurig!. All-Clad pans, and sharp knives. Ice cubes ready on arrival in the freezer. 4. Comfy mattresses and pillows. Reading lights next to the beds. 5. Thick, soft toilet paper. Really. 6. Linda, whose knowledge of the area and proximity and availability for questions was very helpful, especially when my husband couldn't get the washer started because he failed to close the door all of the way. Thanks, Linda.
Stayed 5 nights in Jun 2024

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

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

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

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

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

10/10 Excellent

Anna F., Clarksville, USA

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

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

10/10 Excellent

Sissy H., Bryn Mawr

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

Great location, very comfortable.

Great experience! Highly recommend
Stayed 4 nights in Jun 2021

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