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

Gloucester, Massachusetts
$428 avg/night Minimum Stay 3 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Night 3 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Double-glazed Windows Energy-saving Switches Unit Size: 1100 Sq Ft (102 Sq M) Uses Some LED Lighting Water-efficient Toilets Only
  • KITCHEN

    Blender Coffee Grinder Coffee/tea Maker Dishwasher Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Limited Onsite Parking (max 1 Space) Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Garden Gas Grill Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Fitness Facilities Nearby Golfing On Site Horse Riding Nearby Jet Skiing Nearby Marina Nearby Sailing Nearby Snorkeling Nearby Swimming Nearby Wildlife And Game Walks Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Bay Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Local Meal Delivery Service
  • SUITABILITY/ACCESSIBILITY

    7 Stairs To Reach Property Area Rugs In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevator (single Level Property) Note From Host: Outside Smoking Only Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Review Review

  • Kari

    Submitted May 15, 2022

    Stayed May 8, 2022

    What a pretty cottage! Everything about this little home is perfect, the kitchen is nicely outfitted, the furniture is comfy, the beds were super soft, and there is a wonderful large deck for lounging in the sun and looking out at the harbor. The hosts were available if we needed them but respected our privacy. Thank you so much and we will be back!

  • Submitted Aug 28, 2019

    Stayed Aug 17, 2019

    What a wonderful place for a family vacation! The cottage is perfectly situated between the beautiful Good Harbor Beach and happening downtown Gloucester. The decor was chosen with great care to create a relaxing oasis. The amenities provided everything we needed. Thank you, Linda!

  • Denise

    Submitted Jun 4, 2021

    Stayed May 17, 2021

    Never have I felt as immediately at home as when I stepped through the door into this perfect little cottage. It may not be right on the water, but the view from its spacious deck is spectacular. It allows you to see that Gloucester's harbor is not just a picturesque accessory, but rather a bustling, hard-working home to fishing vessels of all sizes. At the same time, you are in your own serene little piece of this coastal community. Linda and Hank, the owners, live next door and Linda was quickly responsive in helping with a couple of minor issues that arose. Ample info and suggestions for things to do, places to eat, etc. are provided, and Good Harbor Beach is within short, enjoyable walking distance. I would go back tomorrow and never leave if I could!

  • Cassie C.

    Submitted Nov 1, 2025

    Stayed Oct 29, 2025

    We had a great time! Linda the host was awesome super friendly! The house was beautiful, same with the town!

  • Glenda W.

    Submitted Oct 26, 2025

    Stayed Sep 24, 2025

    Properly was very well kept and comfortable. Host was very nice and accommodating. We had a great time.

  • Jennifer B.

    Submitted Oct 12, 2025

    Stayed Oct 9, 2025

    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.

  • Christina M.

    Submitted Oct 7, 2025

    Stayed Oct 2, 2025

    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!

  • Anne S.

    Submitted Jul 1, 2025

    Stayed Jun 16, 2025

    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

  • Kara H.

    Submitted Jun 15, 2025

    Stayed Jun 12, 2025

    The cottage is lovely, spacious and nicely appointed. Great view of the harbor. The hosts were helpful and welcoming.

  • Laura B.

    Submitted Jun 10, 2025

    Stayed Jun 4, 2025

    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.

  • Daniel T.

    Submitted Oct 28, 2024

    Stayed Oct 24, 2024

    Beautiful and peaceful!!!! And the owner was absolutely incredible,

  • Meghan S.

    Submitted Oct 25, 2024

    Stayed Oct 18, 2024

    Lovely house, although a little difficult to get in and out of (the driveway is very narrow). Listing said there was a pull out sofa, but unless I’ve gotten so old I can’t understand how to work it, we couldn’t find the sleeper portion of the sofa. We enjoyed our stay anyway!

  • Brittany K.

    Submitted Oct 20, 2024

    Stayed Oct 11, 2024

    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!).

  • John H.

    Submitted Oct 18, 2024

    Stayed Oct 14, 2024

    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!

  • sylvia g.

    Submitted Oct 12, 2024

    Stayed Oct 8, 2024

    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.

  • Linda D.

    Submitted Sep 30, 2024

    Stayed Sep 27, 2024

    The house was cute. I’ve stayed at several other houses using VRBO and this was my least favorite. The house was not easy for getting vehicles in and out of the area. The towels smelled moldy and the beds and bedding were uncomfortable.

  • Submitted Sep 20, 2024

    Stayed Sep 11, 2024

    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.

  • Frederick M.

    Submitted Jun 26, 2024

    Stayed Jun 2, 2024

    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.

  • Joseph J.

    Submitted Jun 18, 2024

    Stayed Jun 10, 2024

    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.

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Total

Includes taxes and fees
$428+
View details