Verified Review icon 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 pet-dog svg-multiunit Default Owner Icon heart-filled
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful & Luxurious 5BR Wingaersheek Beach House w/Expansive Deck, Multiple Outdoor Showers & Breathtaking Views - Enjoy Private Beach Access!

Bedrooms 5
Space 2,500 sq. ft.
Property type house
Minimum Stay 2 - 7 nights


About the property

Gloucester, Massachusetts

Nestled in a private section of Wingaersheek Beach, this spectacular Gloucester vacation rental home is a tranquil escape for your upcoming oceanside getaway.

Offering 5 bedrooms, 2 bathrooms, and enough sleeping accommodations for 12 guests throughout 2,500 square feet of beautifully appointed living space, this wonderful residence is the perfect size for families or a group of friends out for a rejuvenating beach getaway. The moment you first arrive, you’ll immediately fall in love with the home’s striking open-floor interior, featuring panoramic views of Wingaersheek Beach, the iconic Annisquam Yacht Club, and the beautiful Annisquam and Jones River and marshes. Contemporary decor, unique fixtures, and pops of color make the space very modern, while maintaining an inviting, family friendly vibe. 

Look forward to spending your vacation mornings sipping a hot cup of coffee by the cozy wood burning fireplace, as you admire sweeping views. Expansive windows throughout the home allow you to enjoy the stunning scenery from each room, while living room skylights open and close to let in plenty of natural light. After a pleasant day on the beach, come home and prepare delicious meals in the brand new kitchen, complete with 2 dishwashers, 2 refrigerators, double oven, top-of-the-line Bosch appliances, filtered water, and an ice maker. Later, unwind in the spacious living room, where you can watch your favorite movies on the flat screen TV, while the children can have their own space downstairs for gaming and hanging out. You won’t find it hard to stay entertained here, as the house features 2 additional TVs and is wired inside and out with Sonos music system and surround sound. When you’re ready to call it a night, retire to one of the lovely bedrooms, where you'll sleep easy with plush sleeping accommodations and air conditioning. For your convenience, a top-of-the-line Electrolux washer and dryer is provided in the separate laundry room. 

Experience the best of outdoor living in the home’s stunning exterior space.  Overlooking the beautiful Annisquam River and Yacht Club, the wrap-around deck will quickly become your favorite place to relax and socialize with your companions. Spend your evenings barbecuing on the gas grill, while admiring peaceful sunsets and ever changing tides as boasts sail up and down the river past the Yacht Club. When you return from the beach, rinse the sand off in the outdoor showers before retreating indoors to settle down for the day. It doesn’t get much better than this! 

You can’t beat this home’s phenomenal location. From here, you’ll be a short 350 yard walk away from pristine public and private beaches, where you can enjoy kayaking, paddle boarding, snorkeling, surfing and swimming. Should you find yourself on land, Gloucester offers great restaurants and quaint boutiques. Explore the area further by visiting the small seaside towns nearby, such as Rockport, Manchester-by-the-Sea, Essex, and Salem. Regardless of how you choose to spend your time here, this incredible Wingaersheek Beach vacation rental home will become a place you want to return to year after year! 

Key Residence Features:

- Amenities include a fully equipped kitchen (complete with 2 dishwashers, 2 refrigerators, double oven etc.), wood-burning stove, gas grill, multiple TVs with cable, surround sound, Sonos music system, in-unit laundry machines, air conditioning, wrap-around porch, and private beach access 

- Enjoy picturesque views of the beach, river, and sand dunes from nearly every window

- Walking distance to the beach! 

Bedroom Configuration:

- Master Bedroom: Queen-sized Bed

- Bedroom 2: Full-sized Bed

- Bedroom 3: Full-sized Bed

- Bedroom 4: 2 Twin-sized Beds (bunk beds)

- Bedroom 5: 2 Twin-sized Beds

Additional Sleeping:

- An Air Mattress in the Living Room can accommodate 2 guests


- No smoking

- No pets allowed

- No parties or large gatherings allowed

- Must be at least 25 years old to book

- Additional fees and taxes may apply

More Details

Property Manager
Owner / Property Manager
Speaks: english, french, spanish
Manager indicates their response time is:
Within an hour
Calendar last updated:
April 27, 2017

About Owner / Property Manager

Evolve Vacation Rental Network is on a mission to make vacation rental easy for travelers. Our dedicated Travel Advisor Team is available 7 days a week and our simple online reservation system allows you to book securely with a credit card! Please feel free to call us at 1.877.818.1013.


Gloucester House Accommodation and Amenities

Property Type:
  • house
  • Housekeeper Optional
Floor Area:
  • 2500 sq. ft.
House Rules:
  • Max. occupancy: 12
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters
  • children welcome
Location Type:
  • Beach View
  • Near The Ocean
  • Water View
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Towels Provided
  • Washing Machine
  • Wood Stove
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Refrigerator
  • Stove
  • Toaster
  • 2 Bathrooms
  • 5 Bedrooms, Sleeps 12
  • Master Bedroom - 1 queen , Master Bedroom
    Bedroom 2 - 1 double , Bedroom 2
    Bedroom 3 - 1 double , Bedroom 3
    Bedroom 4 - 2 twin/ single , Bedroom 4
    Bedroom 5 - 2 twin/ single , Bedroom 5
  • Books
  • DVD Player
  • Games
  • Music Library
  • Satellite / Cable
  • Stereo
  • Television
  • Video Games
  • Deck / Patio
  • Outdoor Grill
  • Tennis
  • Long-term Renters Welcome
  • cinemas
  • festivals
  • live theater
  • museums
  • playground
  • restaurants
  • water parks
Leisure Activities:
  • antiquing
  • gambling casinos
  • horseback riding
  • horseshoes
  • sledding
  • whale watching
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • hunting
  • mountain biking
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • surfing
  • swimming
  • tennis


Wonderful! 4.9/5 -
(35 traveler reviews)

Beautiful & Luxurious 5BR Wingaersheek Beach House w/Expansive Deck, Multiple Outdoor Showers & Breathtaking Views - Enjoy Private Beach Access!
average rating of 4.857143 based on 35 reviews

All that and so much more...

  • 5 of 5

We were looking for an early spring getaway on Cape Ann with some water views and this house delivered! We were a little hesitant reading the March 1st review that mentioned scads of issues but we found little to nothing of merit. I am an interior designer by trade, have used a competing rental company for houses as far away as Sonoma, CA and rent out a house we own in the Berkshires so we have some experience in these matters. The house was spacious and clean with glorious views of the beach from atop one of the highest points in the area. Exploring the private part of Wingaersheek reserved for members of this particular area became a daily walk on the beach.

As for the house, the upstairs kitchen was stylish, had all the plates, dishes, linens we could want and personally, a few IKEA pieces juxtaposed with the antique and custom pieces enhanced the modern style of the home. No issues with oven, table legs and switches to speak of and no, not having a vent above an oven is not "illegal" but rather a design choice. We went out for some of our meals and balanced the outings with cooking in. The kitchen is well appointed with high end appliances, many culinary gadgets and we were able to find everything we needed! The bedrooms had comfortable beds and the kids enjoyed having a floor to themselves with several bedrooms and their own bathroom while we slept upstairs.

Overall, the location, the stunning views, the style and spaciousness of the home coupled with the amenities make this hard to beat. We are already planning our return in the Fall!

  • Submitted: Mar 27, 2017
  • Stayed: Mar 2017
  • Source: HomeAway
Did you find this review helpful?
2 0

Overpriced house in disrepair

  • 1 of 5

Three quiet writers rented this house in Gloucester for 5 days -- looking for a peaceful setting to complete our deadlines. Upon check in on Sunday afternoon, we instantly saw that the house was not as advertised: a big water stain on the wood floor downstairs (perhaps from the shower) was the first clue, as was a ceiling light in the laundry room hanging with wires showing. Much more upstairs: missing rugs, a dirty and torn sectional sofa and cheap IKEA chairs in the living room instead of comfortable swivel chairs shown in all the pictures; big wood dining room table with a broken leg, loose kitchen sink faucet with no working sprayer, light fixture switches taped over that didn't work, and -- most worrisome of all -- a sound coming from the oven which turned out to be the fan that would not shut off. We texted the owners who answered a few hours later: they were sorry we were disappointed, blamed everything on previous disastrous renters, and the next day, after several more texts about the condition of the house and the fact that we were going to have to lose time to a repairman for the oven, they offered us two free days. We were not able to extend our stay, nor did we want to, given the house -- and finally owners agreed to give us a partial refund (they dropped off a check and two bottles of wine -- we appreciated the gesture and thanked them). Still not cheap and still missing many of the normal basic amenities for such a rental including: dish soap, shower soap, dish towels, small plates, napkins, working appliances -- including no vent over the stove, which seems illegal, etc. If they'd had renters who had damaged the house, they should have told us in advance of our stay and given us the option of canceling. Certainly they should have alerted us to the oven -- which, after repairman's visit, didn't work at all for the remainder of our stay.

Worst and strangest part was check-out day when owners started dropping off rugs and living room chairs outside before our 11 a.m check out time, then sat in their car waiting for us to leave -- didn't speak to us and barely answered when we spoke to them. We left the property at 11 on the dot with them staring at us from their car. Bizarre and hostile behavior. Shocked by positive comments. Took photos to document.

  • Submitted: Mar 1, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 4

beautiful views and a wonderful stay!

  • 5 of 5

What a wonderful way to gather people together and spend some time in a house with a beautiful location and ALL the comforts of home! Clean and well stocked with everything you need for a perfect stay. Bright, airy and roomy, the house comfortably hosted six adults and accommodated 10 people total during the day. The Hostess was very easy to communicate with, very responsive and went out of her way to make sure everything went smoothly.

  • Submitted: Jan 15, 2017
  • Stayed: Jan 2017
  • Source: HomeAway
Did you find this review helpful?
3 0

Beautiful home, big windows to see the amazing views, great location.

  • 5 of 5

We stayed for 2 nights to toast in the new year.

The house was very open, great kitchen, comfortable furniture and beds. Wingaersheek Beach was an easy walk from the house.

Gloucester has a lot to offer, beautiful beaches, friendly people, quaint downtown, good places to eat.

Our first day we took a food tour and enjoyed some of the local foods and learned about the history of Gloucester.

On day two we had a tour of the Ryan and Wood distillery and walked around Rockport.

In the evening we had a great time cooking, talking, playing games and watching the ball drop in Times Square.

Monica and Steve, thanks for making our NYE so memorable. We look forward to our next visit.

  • Submitted: Jan 2, 2017
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
3 0

What a View!

  • 5 of 5

A lovely warm home with a great view. The owners made it all so very easy.

  • Submitted: Dec 28, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 0

Fantastic Rental!

  • 5 of 5

This is our 2nd year renting this home and we loved it just as much as we did last year. It's the perfect set up for us. The home has everything you need and it's beautifully decorated to top it off. We plan to be back again.

  • Submitted: Dec 19, 2016
  • Stayed: Dec 2016
  • Source: HomeAway
Did you find this review helpful?
3 0


Car: recommended


Rates & Availability


  • Additional fees and taxes may apply

Enter dates for accurate pricing


Partner Offers