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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Photo gallery for Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

A coastal residential area with houses along the beach and rocky outcrops.
A covered porch with a wicker swing, a stone statue, and a staircase leading to a house.
A garden with large rocks, a wooden bench, and a tree with red leaves.
A two-story house with a front porch, a covered patio, and a staircase leading to the upper level.
A spacious living room with a piano, leather sofas, a coffee table, and large windows offering a view of greenery.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Top rated beach location
    Discover paradise at this top rated beach location.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Wingaersheek Beach

Popular amenities

  • Balcony or patio
  • On beach
  • Hot tub on site
  • Arcade/game room
  • Barbecue grill
  • Internet access

Explore the area

View in a map
Gloucester, MA
  • Place, Wingaersheek Beach
    ‪5 min walk‬
  • Place, Good Harbor Beach
    ‪13 min drive‬
  • Place, TD Garden
    ‪58 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪60 min drive‬

Rooms & beds

6 bedrooms (sleeps 15)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

+2
2 Single Beds and 4 Double Beds

Bedroom 5

1 Queen Bed

Bedroom 6

1 Double Futon

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet · Jetted bathtub

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

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About the area

Gloucester

Located in Gloucester, this holiday home is near theme parks and on the beach. The area's natural beauty can be seen at Coolidge Reservation and The Monoliths, while Cape Ann Museum and Maritime Gloucester are cultural highlights. Travelling with kids? Consider Essex Shipbuilding Museum and Cogswell's Grant. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
View more Holiday homes in GloucesterOpens in a new window
Map
Gloucester, MA

What's nearby

  • Wingaersheek Beach - 5 min walk - 0.5 km
  • Stage Fort Park - 9 min drive - 9.2 km
  • Good Harbor Beach - 13 min drive - 12.8 km
  • Encore Boston Harbor - 56 min drive - 57.2 km
  • TD Garden - 58 min drive - 62.5 km

Getting around

  • West Gloucester Station - 7 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 21 min drive

Restaurants

  • ‪McDonald's - ‬9 min drive
  • ‪Dunkin' - ‬8 min drive
  • ‪Chipotle Mexican Grill - ‬9 min drive
  • ‪The Open Door Food Pantry - ‬8 min drive
  • ‪Mile Marker One Restaurant - ‬10 min drive

Frequently asked questions

Is Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam?

As of 24 Oct 2026, prices found for a 1-night stay for 2 adults at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam on 2 Nov 2026 start from £2,496, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam?

On-site parking is available at the property.

What time is check-in at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam?

Check-in begins at 4:00 PM.

What time is check-out at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam?

Checkout is at 10:00 AM.

Where is Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam located?

Nestled on the beach, this Gloucester holiday home is 0.3 mi (0.5 km) from Wingaersheek Beach and 1.7 mi (2.8 km) from Coffins Beach. Pavilion Beach and Massachusetts Bay are also within 6 miles (10 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 54 out of 67 reviews
Rating 8 - Good. 7 out of 67 reviews
Rating 6 - Okay. 3 out of 67 reviews
Rating 4 - Poor. 2 out of 67 reviews
Rating 2 - Terrible. 1 out of 67 reviews

9.0/10

Cleanliness

9.2/10

Check-in

8.6/10

Communication

9.8/10

Location

8.2/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really enjoyed our stay. Plenty of room and close walk to Wingaersheek.
Stayed 7 nights in Aug 2026
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location
Group of 13 for WeddingWe stayed here with a group of 13 for a wedding. The location is great, the neighborhood is nice, the nearby beach is beautiful, and the host was communicative. Biggest issue was that Bedroom 4 was not accurately represented in the listing. It was listed as 2 twin beds and 4 double beds, but was actually two twin bunk beds with twin trundles underneath.We were also required to purchase specific local trash bags ourselves and had to visit multiple stores to find them or be fined. Basic supplies like soap and toilet paper were not provided as indicated, and despite paying a cleaning fee, we were required to wash, dry, and fold all used towels before checkout or be fined. Overall, the house and location were nice, but these inconveniences made the stay disappointing
Stayed 3 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, communication, location
They stay was very nice!
Stayed 4 nights in Sep 2025
Verified review

8/10 Good

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

Great stay for family gathering

House and location supported a relaxing stay with family.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Check-in, location
Disliked: Cleanliness, communication

Great long weekend stay

Beautiful home, close to the beach. Air conditioning wasn’t great and fridge didn’t get very cold. Enjoyed the deck space
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

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

Celebration of life

Beautiful well maintained home. Walking distance to beach.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

Everything we needed for our large family gathering!

Beautiful home, beautiful beaches, great memories for a lifetime. Our host thought of everything we might need and more than we expected.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

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

Beautiful lication

This house is great for large groups. It is so roomy and the location is so beautiful. The beaches are so close. We had a couple bumps but Pete always responded. Would go back for sure!!
Stayed 6 nights in May 2023
Verified review

10/10 Excellent

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

Small Family Bridal shower weekend

The house was just lovely . Plenty of comfortable bedroom's. Comfortable family living room. The bride and groom had a wonderful weekend in master suite . Kitchen was also well stocked for entertaining. I’d so love to rent in the summer months again.
Stayed 2 nights in Mar 2022
Verified review

10/10 Excellent

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

Beautiful home - Beautiful Beaches

Pete’s home is beautiful and well cared for. Pete did his best to assure we were prepared for the stay and aware of the couple of items that there are rules around. The fireplace if for looks only and the jacuzzi tub is not available to use. Just a short 5 minute walk to a prestige beach, 15 minute drive into Salem, and an hour to Boston Logan Airport. We will be staying here again.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Stay without issues

Lovely home! Excellent place for family in town for a wedding; entertaining future in-laws and other out of town guests. Very spacious for bride and bridesmaids to get ready and have photos taken. Very well equipped. Has everything you need for infants (pack-n-play, booster seats, security gates, etc.). Beautiful beach nearby. Almost perfect, could use a fourth bathroom for first floor master bedroom.
Stayed 4 nights in Oct 2023
Verified review

8/10 Good

Liked: Cleanliness, location

Excellent place to stay with friends

For a group of 10 people, the house was very comfortable. Almost everything was provided, except for a few essential items like toilet paper and sugar. The residence is located in a very peaceful neighborhood, close to the sea. The nearest town is about a 10-minute drive away, where you can find everything you might need, such as grocery stores, restaurants, and public transportation to larger cities. During our stay, we had no access to Wi-Fi or TV services.This wasn’t an issue for us, as we were outside all day.
Stayed 3 nights in Oct 2024
Verified review

6/10 Okay

Disliked: Listing accuracy

50th birthday celebration

10 adults. 5 bedrooms/sleeps 12 tops. Arrival 1st day realizing we would have to pick up toilet paper and paper towels for our 4 night trip. All trash to go out end of trip which is fine...but we were to travel into town to go purchase our own bags to use to discard trash. All towels to be washed and dried and put away for 10 people before leaving with 4 laundry pods and a dryer with no heating element working properly. Who doesnt enjoy spending last evening doing laundry??? The house is dated and in need of grneral tlc. The layout of the house is hokey and not user friendly. Besides that, enjoy your stay.
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

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

Family Wedding Weekend

Thank you for a great stay! House was clean and spacious! It accommodated all 15 of us for my nieces wedding. We were able to invite a few more relatives over for breakfast the following morning as we ate on the deck. Aside from celebrating my nieces wedding in Peabody, MA, my sister and her long time fiancé were also married on the private beach just a short walk from the house!!! What a memorable weekend!! The suite on the main floor was perfect for our parents and the 4 bedrooms on the lower level worked well for the rest of us. On our last nite, we all gathered in the lower living room for movie night (yes, our whole crew fit comfortably on the large sectional couch and spacious floor area). My only comment would be the carpets could use some professional cleaning, especially the stairs. We were asked to remove our shoes (which we did and usually do in our own homes), but the light carpets were visibly dirty. Aside from that, it was spotless. I would highly recommend this house. We drove 10 minutes into town and visited some fisherman memorials and ate at a fantastic restaurant. Thank you again to our host Pete! Everything was great!! We’d love to come back again!
Stayed 3 nights in Oct 2022
Response from VrboOwner on 7 Nov 2022
Thank you for the great review and we love being part of making all these memories. We actually had the the rugs scheduled to be steam cleaned a day after your visit and they came out awesome. We typically do them in sept, but got pushed out a month. All good and you guys are welcome back anytime!
Verified review

8/10 Good

Liked: Cleanliness, check-in, location

Great group gathering house (but come prepared!)

We booked the house for our closest friends to stay in during our wedding weekend and the house was great for a group to spend time in together! That said, we came prepared (based on past listings) and still had to adjust expectations on the fly: we brought our own paper towels, toilet paper, hand soap, and tissues (there were minimal or none). We budgeted an extra day in our stay to do the towel washing, dish washing, and trash round up before checking out. We warned guests in advance that sleeping arrangements might be funky and it was; the bed count is slightly inaccurate. There are 3 private rooms with full/queen/king beds and 1 semi private room (it’s a walk-through room). One room with 2 bunk beds + two VERY SMALL pull out mattresses. The bunk bed pillows were terrible too. Lastly the maintenance around the property is minimal. Paint peeling deck, shower drain took forever, signs warning you about issues (like leak under sink, tight refrigerator door, & broken microwave screen) that could definitely just be repaired instead making guests work around it. In summary, if you want a beach vaca for friends and family steps away from the best beach in the state, this house is great. But lower your expectations of the quality of the accommodations!
Stayed 4 nights in Sep 2024
Verified review

4/10 Poor

Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy

Annual Family vacation

The house is very nice but not as stated in listing. There are only 5 bedrooms and so our vacation started out with being 1 bedroom short. Also, no hot tub. There is a jacuzzi bathtub but has a sign stating "do not use". That was one of many signs hung in the house that take away from the experience. There are many breakable items on shelves that have signs stating "personal". One plus is the kitchen is extremely well stocked. The stove is nice but again another sign stating "Do not put the burners on high". The worst was the hot water, or lack of hot water. In the morning the temperature at the boiler was 120 degrees, great. By dinner the temperature was down to 75 degrees. We took at lot of cold showers. I called the owner and he had us look at a couple things. All was as he stated it should be but still not hot water. The beach is very close and beautiful and there are a lot of beach chairs at the house to use. When we left the owner accused us of breaking things that we did not do. Pool sticks were broken when we got there and we took great care of the house and breakable items including obeying all the signs. The house has so much potential but there are too many negatives for me to recommend a stay.
Stayed 7 nights in Jun 2023
Verified review

4/10 Poor

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Location was great, experience was not

Positives: * House was great, it was a wonderful size for our party, we had 3 families in total, 2 families with 2 kids, 1 family with 3. Plenty of room for them to explore and run around. Sleeping accommodations were good, was able to separated the older kids in their own room. * Location was very close to the beach, which provided good entertainment for the family. It was fairly easy to find as well using Google Maps. * Communication - This is going to be split. When we arrived, the owner was pretty responsive and answered our questions. Negatives: * Only initial toiletries provided. Had to go to target to buy our own. * Hot water is an issue if you have people trying to shower/bath during similar times. * Communications leading up to our travel was very lacking. We booked this about a year in advance and tried to reach the owner probably about 12 times, via the app, phone, and email and we received nothing. Even called VRBO to try to reach out and nothing happened. * The day of we were presented with a welcome message that also included additional fees if we didn't do something, one fee for not washing our used towels and folding them and putting back where we got them, and another for not using the proper garbage bags. These specific garbage bags were also not provided and we had to go to a store to buy them ourselves. My big concern with these surprise fees was that it wasn't part of the official booking, which could mean he could charge anything.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect house for our son’s college graduation celebration. Family and friends enjoyed eating lunch on the two decks, playing cornhole in the driveway, shooting pool in the large family room and walking to the beach. The house was fully stocked with everything we needed.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great house! We loved the easy walk to the beach and the cozy space by the kitchen where everyone naturally gathered.
Stayed 3 nights in May 2026
Verified review

2/10 Terrible

Disliked: Cleanliness, check-in, communication, listing accuracy

DO NOT RENT THIS PLACE

The pictures do not represent anything close to what you walk into. The owner is a deceptive, dishonest man who would lead you to believe this home is something that it is definitely not. The only thing that’s accurate about his listing is that it’s near the beach. We made the horrible mistake of leasing the place for our annual 2 week vacation. We arrived late on a Sunday and with our children 2yrs and 4yrs old, as well as the Nanny we brought along with us, tired from the flight. We ran our errands and turned in for the night. We awoke early the next day and went to cook breakfast, I immediately noticed all the patio furniture was shredded and flipped upside down; it looked like it went through a shredder. My Nanny walked upstairs complaining that the plumbing was clogged in the showers and a strange odor was coming from the water. This is literally happening as I’m looking down onto the stove about to cook the eggs (the same commercial stove he advertised in the listing) quickly I realize the stove is completely broken, melted (the burners) the house immediately fills up with gas! I shut the stove off and call the owner. He immediately goes on the defensive and claims ignorance. He then instructed me to “turn on the fan” “because that’s how commercial grade stoves work” being that I own a Wolf stove myself know that he’s full of it. I do so anyway just to entertain my curiosity; but the results are as expected, the house again fills up with gas (quicker then you would ever expect) I then bring up the list of issues we have experienced in the very short time of being there. He said he will send over his handyman in a few hours. So as we wait for the handyman the house starts to get warm as the sun starts to fill the sky and we start to get whiffs of alcohol and vomit through out the house, that quite honestly we didn’t notice when we arrived. We chalked it upto maybe it’s the backed up plumbing or the fact the sun started to warm up the house, either way it was becoming very uncomfortable. Apparently according to the handyman, a large party of over one hundred people took place the night before we checked in. The homeowner was well aware of the condition of the house, stove, plumbing, the worst internet ever, out dated TVs, generally horrible everything! He sent the cleaning crew to mask everything and played dumb when we called. We immediately left on the 2nd day, contacted VRBO, he told them he would refund us the money he lied. The worst!!!
Stayed 13 nights in Aug 2022
Verified review

10/10 Excellent

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

Excellent Stay for our Family.

I booked this home for my family coming in from Texas for my daughter's college graduation. It was perfect for us. House is a little dated, but I'm not complaining since those are just minor updates that was needed. We love to cook, eat, and drink, so the kitchen was a little small to prepare food for a large group. But we managed. The house had more space than you would think, it had space to sleep many more than the 15 person limit that is set. I would rent this house again for my younger daughter's graduation next year if my family decides to come in for that one. I highly recommend this house if you have a large group looking to hold a party or an event. We were able to park 11 cars for the party. Thank you to the Host and to the Owner for such a nice stay.
Stayed 3 nights in Apr 2022
Verified review

10/10 Excellent

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

Gloucester wedding stay

We had a lovely stay in this roomy home, so near to the beach. Although it was a cold, sometimes rainy April stay, the house was comfortable and near to all the attractions . Our daughter got married at Hammond Castle and this rental allowed us to share accommodations with family coming from out of State for the event. The owner/manager was gracious and allowed us to check in a couple of hours early as he had no guests booked for that day and this allowed our out- of- State family to settle in soon after their flight instead of roaming until the official check in time. Thanks again.
Stayed 4 nights in Apr 2022
Verified review

10/10 Excellent

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

stay

Fine stay for adults and older children. I would be nervous having young children upstairs where there are alot of breakables. There is a pool table and air hockey table that are fun, except the pool cues need some tips. Near beaches which is a great plus.
Stayed 4 nights in Nov 2021
Verified review

6/10 Okay

Liked: Cleanliness, location
Disliked: Check-in, communication, listing accuracy

Spacious Home but Exacting Owner with Inaccurate Amenities

I was fairly disappointed with the accuracy regarding the amenities of this property and the communication around our stay. The owner listed a fireplace and a hot tub (this was actually a bathtub jacuzzi) but upon arrival both had signs up saying not to use. The ping pong table had no net, the pool table cues had broken tips, and there was a cable jammed into the wrong part of the TV that made the video game console unusable. Additionally, I was informed only an hour before our check-in time of 4PM on how to access the house, despite having emailed several days in advance and hearing nothing back, and then calling for clarification and being reassured I would be given the details the night before or morning of. I was also then emailed more information that we would need to purchase extra toilet paper if we went through the one allotted roll per bathroom (3) for 10 guests from Fri-Mon, that we needed to stop in town to purchase specific trash bags for the local area, and that we would need to wash, dry and put away the towels before leaving, as well as not only clean but also put back all dishware. If any of these things were not done, it would be a sizable extra fee. I found this to be quite an excessive amount of additional labor, since there was already a cleaning fee. On top of that, it seemed the prior guests or cleaning crew had left a bag of trash in the closet, and we finally realized what this smell was as we were leaving. Understandably, they probably had not gone into town to purchase the specific trash bags, but I was disappointed that the owner/cleaning crew hadn't noticed that before we got there. The location is nice and if you are a large group, the house is big enough to fit comfortably. The beds were fine, some were more comfortable than others. Overall, our stay was satisfactory, but with the amount of extra care we had to take to abide by all the rules and cleaning time, it would have been nice to be provided with the amenities listed or to have extra attention regarding the trash bags/toilet paper. In my opinion, this should be provided by the owner.
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

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

Wonderful experience

Clean house with basic necessities provided. We had a wonderful time and had no issues with this property. Highly recommended.
Stayed 4 nights in Oct 2021
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