check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

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

14 Reviews
Bedrooms 6
Property type house
Minimum Stay 2 - 3 nights

Pay with confidence

When you book through the HomeAway checkout, your booking is backed by our Book with Confidence Guarantee™ offering comprehensive payment protection.

Learn more


Minimum Stay
2 - 3 nights


Gloucester House Rental Photos and Description

5+ bedrooms, 3 full bathrooms, easily sleeps 14+, Plenty of more room available

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!

...... 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.

More Details
  • Groups
  • Low Allergen Environment
  • limited accessibility
  • non smoking only
  • pets not allowed

Pete Cast
Member since: 2011
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
October 24, 2016
Call Owner

What makes this house 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


based on 14 traveler reviews

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam
average rating of 5.0 based on 14 reviews

beautifully maintained property and ideal location

  • 5 of 5

My extended family of 13 stayed here in August 2016 and had a fabulous vacation. Perfectly situated for access to both the public and private beaches at Wingaersheek. The property is spacious and beautifully maintained and the kitchen is well stocked with utensils for a large group, including lobster pots. Highly recommend.

  • Submitted: Oct 10, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

Wonderful house!

  • 5 of 5

My wedding party and I stayed in this house for the wedding weekend and it was amazing! Beautiful rooms and plenty of space for all. The house was clean and so close to the beach (the rainy weather didn't deter us from making a quick trip)! Only wish we could have stayed longer :-)

  • Submitted: Oct 7, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
Did you find this review helpful?
0 0
New York City

As Always a Pleasure

  • 5 of 5

This house is one of our favorites. The is the 2nd time we have stayed at this home & the owner (Pete) is very easy to work with. He made sure out stay was nothing short of perfect for both our 1st and 2nd stints at his beachside home. We initially rented this property for our wedding home to house the wedding party since it was large and the Gloucester market doesn't have large hotel vacancies. Pete took us in & everything was better than any hotel we could've imagined. As an anniversary gift for my wife I decided to surprise her with a trip on our anniversary back to the same house and she couldn't have been happier. We might make it lucky #3 next year! The private Waterman community beach is nothing short of spectacular just a short walk up the hill from the house. There is plenty of bathroom and bedroom space for friends and family. Thanks so much for everything.

Ryan D

  • Submitted: Sep 13, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
Did you find this review helpful?
0 0
Albany, NY

Beautiful Home for a Family Gathering

  • 5 of 5

We have stayed at one of Pete's homes for several years now. They are beautiful, clean and nicely stocked with games and kitchen necessities. The Waterman home provided plenty of space for all of our kids and their families to relax and enjoy each other and the area. We are beach folks, so we took advantage of both Wingersheek Beach (just a short walk from the house) and Good Harbor.. Both have their own uniqueness.

Pete is quickly available for questions and concerns. Both he and his wife are friendly and helpful people, who want you to enjoy your vacation in Gloucester. My six year old grandaughter said of their place "It's the nicest resort she's every been to" I think she's right.

  • Submitted: Sep 1, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

A beautiful home at the beaches

  • 5 of 5

This was our second year at this lovely home. The home and grounds are well kept. The house is always clean and ready for our stay. There are twelve of us , six are children, there is so much room to either be together or have a little private space. The two beaches are clean and beautiful.. We have tide pool hunters and they spend hours at either beach searching for sea creatures. The kitchen is well appointed. We never have a need for something we can not find . The owner and caretaker are great to work with and very friendly.. We almost feel like we have made new friends. There are places to visit near by if you don't want a day at the beach.. A farmers market is close with great fresh produce. We highly recommend this lovely home and look forward to staying again.

  • Submitted: Aug 22, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

Beautiful House, Beautiful Location

  • 5 of 5

This is a beautiful house, in a beautiful setting. Very quiet and peaceful! The house was very clean, and in perfect condition. It is very well-cared for. The owner was great to work with - very helpful and responsive. I definitely recommend this home, and hope to come back again.

  • Submitted: Jun 13, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
Did you find this review helpful?
0 0


Car: recommended

More pictures and information available. Please make a request or make a suggestion. NOTE: If you are looking for an additional house/property. Please view our sister-house at Homeaway Listing # P3523865 or VRBO Listing # P3523865 located less than a .14 mile away, and located in the private section of the beach as well. HomeAway 3523865

Absoluetly NO smoking or Pets allowed. For the safety and comfort of all current and future guests.


Rates & Availability

Gloucester House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Post-Summer/ Early Autumn 2016
Sep 8 2016 - Dec 3 2016
3 night minimum stay
Autumn/Fall 2016
Dec 4 2016 - Jan 4 2017
3 night minimum stay
Winter/Early Spring 2017
Jan 5 2017 - Mar 30 2017
2 night minimum stay
Pre-Summer 2017
Mar 31 2017 - Jun 2 2017
3 night minimum stay
Summer 2017
Jun 3 2017 - Sep 9 2017
3 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

Summer Rentals are Saturday to Saturday. Additional Charges may apply for Holiday weekends

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
Send a Message
Available arrival
Available stay (no arrival)


Gloucester House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 4000 sq. ft.
Location Type:
  • Beach
  • Beach View
  • Beachfront
  • Near The Ocean
  • Ocean View
  • Oceanfront
  • Waterfront
  • Family
  • Activities Guide
  • Air Conditioning
  • Alarm Clock
  • Alarm System
  • Baby Gate
  • Backpack
  • Basic Soaps
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer
  • Evaporative Cooling
  • Filtered Water
  • Fireplace
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Living Area
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Mobile Phone
  • Paper Towels
  • Parking
  • Parking Off Street
  • Secure Parking
  • Security System
  • Sofa Bed
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Water Cooler
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Gourmet Kitchen
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Room
  • seating for 10 people
  • 3 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , jetted tub
    Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - toilet , combination tub/shower
  • 6 Bedrooms, Sleeps 15
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 king
    Bedroom 3 - 1 queen
    Bedroom 4 - 4 double , 2 twin/ single , two bunk bed with pull out trundles
    Bedroom 6 - 1 sleep sofa /futon , full size pull out sofa set
    Bedroom 5 - 1 queen
  • Please ask if any questions
  • Audio Tape Player
  • DVD Player
  • Game Room
  • Games
  • Games for Kids
  • MP3 Dock
  • Piano
  • Ping Pong Table
  • Pool Table
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Video Game Console
  • Video Games
  • Balcony
  • Beach Chairs
  • Beach Towels
  • Beach Umbrellas
  • Deck / Patio ...
  • Deck Furniture
  • Fully Fenced Property
  • Gated Community
  • Lanai / Gazebo ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Entertainment Area
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Porch Furniture
  • Small Cooler
  • Tennis Court
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Wood Deck
  • Yard
  • 8 garden chairs
  • 4 beach chairs
  • Groups
  • Low Allergen Environment
  • limited accessibility
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Indoor Hot Tub
Onsite Services:
  • Car Optional
  • arboretum
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • theme parks
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • gambling casinos
  • horseback riding
  • outlet shopping
  • paddle boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • jet skiing
  • pier fishing
  • rafting
  • rock climbing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Please ask any questions.

Partner Offers