Title: Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=8008&destination=Gloucester%2C+Massachusetts%2C+United+States+of+America&selected=23710091&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester ## Photo gallery for Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester ![Beach nearby, sun loungers, beach towels - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)](https://images.trvl-media.com/lodging/24000000/23720000/23710100/23710091/0a0a7342.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV, DVD player, books, video library - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)](https://images.trvl-media.com/lodging/24000000/23720000/23710100/23710091/5c3437b5.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Marina - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)](https://images.trvl-media.com/lodging/24000000/23720000/23710100/23710091/91e56ab0.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)](https://images.trvl-media.com/lodging/24000000/23720000/23710100/23710091/6f50cb12.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining - Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester (Gloucester)](https://images.trvl-media.com/lodging/24000000/23720000/23710100/23710091/4d1e8140.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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 Exceptional ### Entire home 2 bedrooms1 bathroomSleeps 41100 sq ft ## Popular amenities - Ocean view - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## 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 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 ## Similar properties ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2803800/2803719/5bb839c9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Rockport Inn And Suites Rockport - Pool - Breakfast included - Pet friendly - Parking included 8.6 Excellent 1,544 reviews CA $151 CA $169 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24&selected=2803719&PinnedHotelID=2803719&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15380000/15379900/15379825/70af0ced.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beauport Hotel Gloucester Downtown Gloucester - 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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 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 Property Registration Number 0033061070 ### We should mention A car is recommended for transportation 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 vacation home is in East Gloucester, a neighborhood 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. Be sure to check out the area's animals with activities such as game walks and birdwatching. [Visit our Gloucester travel guide](https://www.expedia.ca/Gloucester.dx8008) [View more Vacation homes in Gloucester](https://www.expedia.ca/Gloucester-Private-Vacation-Homes.d8008-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C42.61274%2C-70.64780&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=RHwZfeNhgY4YOu_Oun3UdD5vjkk=) Gloucester, MA ### What's nearby - ![Good Harbor Beach featuring a sunset, a sandy beach and general coastal views](https://images.trvl-media.com/place/553248621532667409/fda0f2a2-9a66-4e87-a0d4-6552f49b1eaf.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Good Harbor Beach 16 min walk \- 1.4 km - ![Cape Ann Museum featuring art and interior views](https://images.trvl-media.com/place/553248621532667408/47204162-37ed-4077-9c87-aeb1105d0acb.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Cape Ann Museum 2 min drive \- 1.5 km - ![Maritime Gloucester as well as a small group of people](https://images.trvl-media.com/place/553248621532667406/1591d05f-3f58-412a-a304-a1272214e614.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Maritime Gloucester 2 min drive \- 1.8 km - ![Niles Beach featuring general coastal views, a bay or harbor and a beach](https://images.trvl-media.com/place/553248621561735327/2eba14da-d82d-4b8f-8bd1-c634bd89125b.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Niles Beach 2 min drive \- 2.9 km - Rocky Neck Art Colony 18 min walk \- 1.5 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? ### How much is parking? ### What time is check-in at Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester? ### What time is check-out at Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester? ### Where is Harbor View Retreat with Large Private Deck - Walk to Downtown Gloucester located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## 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 information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 128 8 - Good 7 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.8 Location ### 10 Staff & service ### 9.0 Property conditions & facilities ## Reviews Verified ### 10/10 Excellent #### Cassie C. Nov 1, 2025 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! ##### Cassie C. Stayed 3 nights in Oct 2025 Verified ### 10/10 Excellent #### Glenda W. Oct 26, 2025 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. ##### Glenda W. Stayed 5 nights in Sep 2025 Verified ### 10/10 Excellent #### cmcdanie74 Nov 6, 2023 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. ##### cmcdanie74 Stayed 4 nights in Oct 2023 Verified ### 10/10 Excellent #### Daniel T. Oct 28, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 30th Anniversary Beautiful and peaceful!!!! And the owner was absolutely incredible, ##### Daniel T. Stayed 4 nights in Oct 2024 Verified ### 10/10 Excellent #### Kristin A. Sep 11, 2023 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!! ##### Kristin A. Stayed 4 nights in Sep 2023 Verified ### 10/10 Excellent #### Jim O. Aug 14, 2023 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. ##### Jim O. Stayed 7 nights in Aug 2023 Verified ### 10/10 Excellent #### Amanda A. Oct 21, 2023 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. ##### Amanda A. Stayed 3 nights in Oct 2023 Verified ### 10/10 Excellent #### Sherry K. Jul 30, 2023 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! ##### Sherry K. Stayed 7 nights in Jul 2023 Verified ### 10/10 Excellent #### Verified traveller Sep 20, 2024 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. ##### Verified traveller Stayed 7 nights in Sep 2024 Verified ### 10/10 Excellent #### Rute F. Sep 6, 2023 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! ##### Rute F. Stayed 7 nights in Aug 2023 Verified ### 10/10 Excellent #### Nathalie D. Sep 15, 2023 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) ##### Nathalie D. Stayed 4 nights in Sep 2023 Verified ### 10/10 Excellent #### John H. Oct 18, 2024 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! ##### John H. Stayed 4 nights in Oct 2024 Verified ### 10/10 Excellent #### sylvia g. Oct 12, 2024 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. ##### sylvia g. Stayed 3 nights in Oct 2024 Verified ### 10/10 Excellent #### Brittany K. Oct 20, 2024 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!). ##### Brittany K. Stayed 3 nights in Oct 2024 Verified ### 10/10 Excellent #### Dusty S. Sep 19, 2023 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. ##### Dusty S. Stayed 3 nights in Sep 2023 Verified ### 10/10 Excellent #### Frederick M. Jun 26, 2024 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. ##### Frederick M. Stayed 7 nights in Jun 2024 Verified ### 10/10 Excellent #### Joseph J. Jun 18, 2024 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. ##### Joseph J. Stayed 5 nights in Jun 2024 Verified ### 10/10 Excellent #### Jennifer B. Oct 12, 2025 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. ##### Jennifer B. Stayed 3 nights in Oct 2025 Verified ### 10/10 Excellent #### Laura B. Jun 10, 2025 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. ##### Laura B. Stayed 5 nights in Jun 2025 Verified ### 10/10 Excellent #### Christina M. Oct 7, 2025 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! ##### Christina M. Stayed 3 nights in Oct 2025 Verified ### 10/10 Excellent #### Kara H. Jun 15, 2025 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. ##### Kara H. Stayed 3 nights in Jun 2025 Verified ### 10/10 Excellent #### Anna F. Aug 18, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Location and Peaceful Stay Great Hospitality from the Hosts. Quiet. ##### Anna F. Stayed 7 nights in Jun 2023 Archival ### 8/10 Good #### Kim M. Oct 1, 2017 #### 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. ##### Kim M. Stayed 4 nights in Sep 2017 Verified ### 10/10 Excellent #### Sissy H. Jun 17, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location, very comfortable. Great experience! Highly recommend ##### Sissy H. Stayed 4 nights in Jun 2021 Verified ### 10/10 Excellent #### Regina B. Jul 9, 2019 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! ##### Regina B. 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