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

As of 19 Sept 2025, prices found for a 1-night stay for 2 adults at Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam on 5 Oct 2025 start from NZ$2,762.26, 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.

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam Reviews, Deals & Photos 2025

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

No, pets are not allowed at this property.

Q: 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).

10/10 Excellent

Nancy L.

12 May 2025

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

8/10 Good

Joe P.

31 Jul 2024

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

10/10 Excellent

Katrine H.

3 Aug 2024

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

10/10 Excellent

Jackie A.

20 Oct 2024

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

10/10 Excellent

Sandra R.

2 Jun 2023

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

8/10 Good

Catherine G.

14 Nov 2024

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

10/10 Excellent

Louise K.

31 Mar 2022

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

10/10 Excellent

Barbara D.

2 Sept 2019

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

Another Year at Waterman

The house on Waterman is a beautiful home. We have stayed there for several years. You have a short walk to either the public or private beach. The kids who love the surf can get plenty with a quick drive to Good Harbor Beach. Pete and Tracy are great with any issues and respond quickly.

Stayed 7 nights in Aug 2019

10/10 Excellent

Connie W.

16 Oct 2023

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

6/10 Okay

Amy N.

3 Nov 2023

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

8/10 Good

Anya W.

10 Sept 2024

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

10/10 Excellent

Sharon S.

23 Oct 2022

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

4/10 Poor

Jane Y.

25 Jul 2023

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

4/10 Poor

Kevin N.

18 Oct 2023

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

10/10 Excellent

Jacalyn H.

16 Dec 2024

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

Stayed 3 nights in Nov 2024

10/10 Excellent

Madalyn S.

19 Nov 2024

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

Stayed 3 nights in Oct 2024

2/10 Terrible

Shawn F.

20 Oct 2022

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

10/10 Excellent

Alex N., SALISBURY, MA USA

13 May 2022

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

10/10 Excellent

Diane and Doug S.

22 Apr 2022

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

10/10 Excellent

Priscilla L.

28 Nov 2021

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

6/10 Okay

Michelle W.

8 Nov 2021

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

10/10 Excellent

James D.

7 Nov 2021

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

10/10 Excellent

Liz N., Concord, MA

23 Sept 2021

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

Great beach getaway!

Location, location, location! This property is situated within close walking distance of both Wingaersheek and Coffins beaches, which made going back and forth to the beach super easy, even with smaller children in the mix. We were 2 families -- of 5 and 4 -- and the layout of the house was pretty perfect for us. There are two larger bedrooms for the adults, and a good mix of sleeping options for our kids -- two smaller rooms, each with a queen bed, and a larger room with 2 bunk beds (with trundles underneath if necessary). There also are two sitting areas for hanging out and watching TV, which worked well for our teens who preferrd to hang out in their own space a lot of the time. The owner was very responsive to questions and a couple of smaller issues throughout our stay and the house was pretty well equipped. We spent most of our time at Wingaersheek beach, which is an ideal beach for kids, but also enjoyed taking walks along the quieter long stretch of the private Coffins beach. We also enjoyed outings to downtown Gloucester and Rockport, an easy drive away. You really can't beat the location of this house in this price range -- it's pretty much as close to beach as one can get without actually being ON the beach. We had an awesome vacation week and I can't wait to rent it again!

Stayed 8 nights in Aug 2021

8/10 Good

Marla D.

20 Aug 2021

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

Disliked: Communication

Great location

This home was in a great location. The grill out on the deck was not clean. The host promised to send someone to clean it but this never happened. The deck had a couple of loose boards.

Stayed 7 nights in Jul 2021

10/10 Excellent

Verified traveller

10 Aug 2021

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

Perfect spot

We had a great stay here! With a bunch of kids in the mix, the proximity to Wingaersheek beach and the other private beach was such an amazing part of our daily experience there. Lots of open living space, great communication with Pete, and fun stuff to do both inside and outside.

Stayed 7 nights in Jul 2021

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

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