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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
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Reviews
9.4 out of 10
Exceptional
6 bedrooms 3 bathrooms Sleeps 15 371.6 sq m
Popular amenities
Explore the area

Gloucester, MA
- Place, Wingaersheek Beach5 min walk
- Place, Hammond Castle
- Place, Good Harbor Beach12 min drive
- Airport, Boston, MA (BOS-Logan Intl.)49 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
About this property
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
This is the vacation house you have been looking for! Perfectly located only a few steps from the world famous Wingaersheek Beach, as well as, your own private access to Coffins beach. The younger crowd will love the excitement of the public part of Wingaersheek beach, while the private access to Coffins Beach is unexcelled for that quiet relaxing time. Why have to make a choice when you can have them both? All within a few minutes walk (300 yards) to the white sands of the public side of Wingaersheek beach or less than 2/10 of a mile to the private neighborhood section of the beach called Coffins beach. This immaculate and graciously appointed home is the perfect destination for discerning beach lovers who want only the best in accommodation, sea & surf!
Housing accommodations are a perfect set-up for the extended family or share with the best friends. This location contains 4000 sq/ft. of housing for your enjoyment. This is one of the biggest houses available in the area. Once you enter the driveway and proceed up to the house you will immediately feel like you are on vacation and ready to enjoy your stay. There are numerous outdoor custom built-in mahogany sitting benches and patios to enjoy the beautiful weather and enjoy the wonderful landscape from the deck swing. As you walk-in the first floor entrance into the spacious custom tiled foyer entrance, you will immediately feel the beach house charm! The rest of the first floor contains an expansive in-law/au-pair suite, which is on your left down a few steps into a very large queen bedroom with a sitting area with TV and cathedral ceilings. You will also find the separate laundry room off the entrance foyer. To your right you will find two more large bedrooms and two custom full-size bathrooms as well. Don’t forget the additional Wifi equipped office space which can be used as a bedroom if needed. The rest of the first floor living room contains a large TV, and a spacious and comfy living room set, and don’t forget you can always challenged each other at the 3-in-1 game table (your choice of pool, ping pong and air hockey) Once you climb the stairs to the second floor you will find the gourmet kitchen featuring a world-class WOLF commercial gas stove. The granite counters, custom cabinets, and oversized chef's gas stove (complete with pot-filling faucet), pantry and stainless appliances completes this home so that it is the perfect place to be the ultimate beach home away from home. Produce your family’s favorite recipes or try some of the great local dining options, its all up to you. Beyond the 8 chair kitchen, you can relax at the kitchen nook by the fireplace, or continue to the formal dining area. The open concept dining room with seating for up to 10 is surrounded on two sides by custom built-in shelving, this in turn leads into the gorgeous Living room where you can view the surroundings from the stunning Palladian windows, surrounding you on all sides. This area doubles as another gathering place to relax with a plush leather sitting area open to the kitchen making it a great space for entertaining as everyone can be together (but still out of the cooks way) in comfort! The king sized master bedroom with cathedral ceilings is located on this floor as well. It contains your own custom full-sized bathroom and another sofa set with a hidden TV, and of course your own large private mahogany deck. The King size bed actually looks small in this space! The house is air conditioned if you prefer, or you can enjoy the sea-breeze air and open the three sets of oversized Anderson sliders. (Five sets if you combine both floors!) Which open onto to the expansive upper mahogany decks, where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer? The house has wifi, of course, but bring your cell phone as there is no landline at the house. Plenty of parking in the driveway and lovely landscaping outside! Additionally, Gloucester is becoming a more and more artwork-culturally known area; take a ride to the local artwork shops found around Rocky Neck. Find your next treasure to remind you of your stay. There is everything you would expect for a great ocean beach stay, located only 10-15 minutes drive to Gloucester harbor. Once you experience this vacation house and locale, you will want to return for years to come. Start a new tradition and make a reservation today!
Please note: our cancellation policy is if you need to cancel, it is based on our ability to re-rent the booked time, and we always have fulfilled any cancellation.
...... Exciting news, we are adding a Classic restored 1965 Pontiac GTO or a 1986 Trans Am for rental during visiting guest stays. Enjoy the area even more in a Classic GTO or Trans Am. Please ask about rates and pictures if interested.
Housing accommodations are a perfect set-up for the extended family or share with the best friends. This location contains 4000 sq/ft. of housing for your enjoyment. This is one of the biggest houses available in the area. Once you enter the driveway and proceed up to the house you will immediately feel like you are on vacation and ready to enjoy your stay. There are numerous outdoor custom built-in mahogany sitting benches and patios to enjoy the beautiful weather and enjoy the wonderful landscape from the deck swing. As you walk-in the first floor entrance into the spacious custom tiled foyer entrance, you will immediately feel the beach house charm! The rest of the first floor contains an expansive in-law/au-pair suite, which is on your left down a few steps into a very large queen bedroom with a sitting area with TV and cathedral ceilings. You will also find the separate laundry room off the entrance foyer. To your right you will find two more large bedrooms and two custom full-size bathrooms as well. Don’t forget the additional Wifi equipped office space which can be used as a bedroom if needed. The rest of the first floor living room contains a large TV, and a spacious and comfy living room set, and don’t forget you can always challenged each other at the 3-in-1 game table (your choice of pool, ping pong and air hockey) Once you climb the stairs to the second floor you will find the gourmet kitchen featuring a world-class WOLF commercial gas stove. The granite counters, custom cabinets, and oversized chef's gas stove (complete with pot-filling faucet), pantry and stainless appliances completes this home so that it is the perfect place to be the ultimate beach home away from home. Produce your family’s favorite recipes or try some of the great local dining options, its all up to you. Beyond the 8 chair kitchen, you can relax at the kitchen nook by the fireplace, or continue to the formal dining area. The open concept dining room with seating for up to 10 is surrounded on two sides by custom built-in shelving, this in turn leads into the gorgeous Living room where you can view the surroundings from the stunning Palladian windows, surrounding you on all sides. This area doubles as another gathering place to relax with a plush leather sitting area open to the kitchen making it a great space for entertaining as everyone can be together (but still out of the cooks way) in comfort! The king sized master bedroom with cathedral ceilings is located on this floor as well. It contains your own custom full-sized bathroom and another sofa set with a hidden TV, and of course your own large private mahogany deck. The King size bed actually looks small in this space! The house is air conditioned if you prefer, or you can enjoy the sea-breeze air and open the three sets of oversized Anderson sliders. (Five sets if you combine both floors!) Which open onto to the expansive upper mahogany decks, where you can relax on the outside deck furniture and sunbath privately instead of the beach if you prefer? The house has wifi, of course, but bring your cell phone as there is no landline at the house. Plenty of parking in the driveway and lovely landscaping outside! Additionally, Gloucester is becoming a more and more artwork-culturally known area; take a ride to the local artwork shops found around Rocky Neck. Find your next treasure to remind you of your stay. There is everything you would expect for a great ocean beach stay, located only 10-15 minutes drive to Gloucester harbor. Once you experience this vacation house and locale, you will want to return for years to come. Start a new tradition and make a reservation today!
Please note: our cancellation policy is if you need to cancel, it is based on our ability to re-rent the booked time, and we always have fulfilled any cancellation.
...... Exciting news, we are adding a Classic restored 1965 Pontiac GTO or a 1986 Trans Am for rental during visiting guest stays. Enjoy the area even more in a Classic GTO or Trans Am. Please ask about rates and pictures if interested.
Add dates for prices
Amenities
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
- Kitchen
- Washer
- Dryer
- Air conditioning
9.8 out of 10, (25 reviews)
House Rules
Check in after 4:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
Events allowed
@25-30 Guest Max
Pets
No pets allowed
Smoking
Smoking is not permitted
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
Parties and events are allowed on site
Note from host: @25-30 Guest Max
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, a first aid kit and a deadlock
Property Registration Number C0150631070
We should mention
A car is recommended for transport to and from this property
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 Wingaersheek Beach and Good Harbor Beach. Travelling with kids? Consider Maritime Gloucester and Schooner Adventure. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Gloucester, MA
What's nearby
- Wingaersheek Beach - 5 min walk - 0.5 km
- Maritime Gloucester - 10 min drive - 8.9 km
- Half Moon Beach - 10 min drive - 8.9 km
- Good Harbor Beach - 12 min drive - 11.1 km
- Plum Cove Beach - 15 min drive - 13.2 km
Getting around
Restaurants
- McDonald's - 9 min drive
- Starbucks - 9 min drive
- Dunkin' - 8 min drive
- George's Coffee Shop - 7 min drive
- Mile Marker One Restaurant - 10 min drive
Frequently asked questions
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 window9.0/10
Cleanliness
9.2/10
Check-in
8.4/10
Communication
9.8/10
Location
8.4/10
Listing accuracy
Reviews
23 June 2025
Liked: Check-in, location
Disliked: Cleanliness, communication
Stayed 3 nights in Jun 2025
10/10 Excellent
Nancy L.
12 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Celebration of life
Nancy L.
Stayed 4 nights in May 2025
8/10 Good
Joe P.
31 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for family gathering
Joe P.
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!
Katrine H.
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
Jackie A.
Stayed 3 nights in Oct 2024
10/10 Excellent
Sandra R.
2 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful lication
Sandra R.
Stayed 6 nights in May 2023
8/10 Good
Catherine G.
14 Nov 2024
Liked: Cleanliness, location
Excellent place to stay with friends
Catherine G.
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
Louise K.
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
Barbara D.
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
Connie W.
Stayed 4 nights in Oct 2023
6/10 Okay
Amy N.
3 Nov 2023
Disliked: Listing accuracy
50th birthday celebration
Amy N.
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!)
Anya W.
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
Sharon S.
Stayed 3 nights in Oct 2022
4/10 Poor
Jane Y.
25 July 2023
Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy
Annual Family vacation
Jane Y.
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
Kevin N.
Stayed 4 nights in Sep 2023
10/10 Excellent
Diane C.
13 Sept 2025
Diane C.
Stayed 7 nights in Aug 2025
10/10 Excellent
Jacalyn H.
16 Dec 2024
Liked: Cleanliness, check-in, location, listing accuracy
Jacalyn H.
Stayed 3 nights in Nov 2024
10/10 Excellent
Madalyn S.
19 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Madalyn S.
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
Shawn F.
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.
Alex N.
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
Diane and Doug S.
Stayed 4 nights in Apr 2022
10/10 Excellent
Priscilla L.
28 Nov 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
stay
Priscilla L.
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
Michelle W.
Stayed 3 nights in Oct 2021
10/10 Excellent
James D.
7 Nov 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful experience
James D.
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!
Liz N.
Stayed 8 nights in Aug 2021
About the host
Hosted by Pete Cast

Why they chose this property
What makes this property unique
Please view our sister-house at Homeaway Listing # 3523865 or VRBO Listing # 3523865ha located less than a 1/3 mile away, and located in the private section. of the beach as well. HomeAway 3523865
Or our additional spectacular Location on Long Beach in Gloucester Homeaway listing Number: 3827982
Or our additional spectacular Location on Long Beach in Gloucester Homeaway listing Number: 3827982
Languages:
English
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