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

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Beach nearby, sun-loungers, beach towels
Outdoor dining
Beach nearby, sun-loungers, beach towels
Beach nearby, sun-loungers, beach towels
Marina

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

Explore the area

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

Room options

About the area

Gloucester

This holiday home places you in the centre of Gloucester, within just a 15-minute stroll of Massachusetts Bay and The Gorton Theatre. Highlights at this holiday home include a kitchen, a washer/dryer and free WiFi. .You can enjoy Smart televisions with a DVD player, and home features a patio, a dining area and a coffee/tea maker. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a TV and a hairdryer are also available. .This smoke-free holiday home offers a garden and gas grills. Additionally, you'll find laundry facilities. .Sights within a 20-minute walk of this East Gloucester holiday home include Good Harbor Beach and Rocky Neck Art Colony.
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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
  • ‪Dunkin' - ‬2 min drive
  • ‪The Burn Tavern - ‬19 min walk
  • ‪The Lobster of Gloucester - ‬3 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.

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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

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. Note from host: Absolutely no partying. Quiet neighborhood. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all accommodation.

Property Registration Number 0033061070

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

Are there any beaches close to Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

Yep, Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck is a short 16-minute walk from Good Harbor Beach. Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find motor boats.

Does Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

No, Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck does not offer an airport shuttle service.

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

Check-in begins at 3:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck?

No, pets are not allowed.

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

10/10 Excellent

Cassie C.

Liked: Cleanliness
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

Glenda W.

Liked: Cleanliness
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

Jennifer B.

Liked: Cleanliness
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

Christina M.

Liked: Cleanliness
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

Anne S.

Liked: Cleanliness

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

10/10 Excellent

Kara H.

Liked: Cleanliness
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

Laura B.

Liked: Cleanliness
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

Daniel T.

Liked: Cleanliness

30th Anniversary

Beautiful and peaceful!!!! And the owner was absolutely incredible,
Stayed 4 nights in Oct 2024

8/10 Good

Meghan S.

Liked: Cleanliness

Fall Getaway

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!
Stayed 3 nights in Oct 2024

10/10 Excellent

Brittany K.

Liked: Cleanliness

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

John H.

Liked: Cleanliness

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

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

8/10 Good

Linda D.

Liked: Cleanliness

Cute little house

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.
Stayed 3 nights in Sep 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness

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

Frederick M., Ammon, ID

Liked: Cleanliness

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

Joseph J., Sycamore, IL

Liked: Cleanliness

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

cmcdanie74

Liked: Cleanliness

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

Amanda A.

Liked: Cleanliness

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

Dusty S.

Liked: Cleanliness

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

Nathalie D.

Liked: Cleanliness

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

Kristin A., Trumbull, CT

Liked: Cleanliness

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

Rute F.

Liked: Cleanliness

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

Anna F., Clarksville, USA

Liked: Cleanliness

Great Location and Peaceful Stay

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

10/10 Excellent

Jim O.

Liked: Cleanliness

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

Sherry K.

Liked: Cleanliness

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