Entire home

Stay at Wingaersheek

Photo gallery for Stay at Wingaersheek

An aerial view of a residential area with houses, a beach, and a body of water.
Private beach adjacent to Wingaersheek, just 2 minutes from the property.
A two-story house with a balcony, a covered patio, and a view of a lake.
A wooden deck with white railings, overlooking a residential area and the ocean.
A spacious living room with a flat-screen TV, a ceiling fan, and a large window offering a view of the outdoors.

Highlights

  • Discover nearby landmarks
    Close to Wingaersheek Beach
3 bedrooms3+ bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony

Explore the area

View map
Gloucester, Massachusetts
  • Place, Wingaersheek Beach
    ‪6 min walk‬
  • Place, Half Moon Beach
    ‪12 min drive‬
  • Place, Good Harbor Beach
    ‪14 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪60 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Living Room 1

1 Double Sofa Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Toilet

Spaces

Kitchen
Office
Balcony
Garden

About this property

Stay at Wingaersheek

Summary:

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features:



✓ 2-minute walk to private beach access between Wingaersheek Beach and Coffins Beach

✓ Panoramic water views from two expansive decks

✓ Sleeps 8 across 3 bedrooms, 5 beds and 3.5 baths

✓ Quiet coastal setting near Gloucester, Essex, and Ipswich



See more photos, video tours, and local recommendations on IG @staycapeann.



The Space:

Tucked away on Gloucester's coveted Wingaersheek peninsula, this three-story coastal retreat was designed to showcase the water from nearly every angle. Wake up to panoramic views, spend your days exploring nearby beaches, and unwind each evening on one of two waterview decks as the sun sets over the coast.



Located just a short walk from private beach access nestled between Wingaersheek Beach and Coffins Beach, the home offers a rare combination of privacy, scenery, and convenience. Hardwood floors, bright living spaces, and a thoughtful multi-level layout provide plenty of room for families and groups to spread out while staying connected.



★★★ HIGHLIGHTS ★★★



→ Private beach access just a 2-minute walk away

→ Water views throughout the home

→ Two spacious decks with outdoor dining and lounge seating

→ Quiet coastal neighborhood surrounded by beaches and natural beauty

→ Sleeps up to 8 guests across 3 bedrooms (5 beds) and 3.5 baths



★★★ 1ST FLOOR ★★★



→ Kitchen: Fully equipped with everything needed for cooking and entertaining

→ Dining Area: Table with bench seating framed by floor-to-ceiling windows and water views

→ Living Room: Comfortable gathering space with abundant natural light and coastal scenery

→ Bedroom 1: Queen bed with en-suite bathroom

→ Bedroom 2: Two twin beds in a spacious room

→ Bathroom: Full bathroom conveniently located on the main level



★★★ 2ND FLOOR ★★★



→ Primary Suite: King bed, exposed beams, private deck access, and beautiful water views

→ En-Suite Bath: Private full bathroom

→ Queen-size pull-out sofa for additional sleeping

→ Large second living room with amazing water views and ample seating



★★★ OUTDOOR LIVING ★★★



→ Upper Deck: Lounge seating, and sweeping water views

→ Lower Deck: Outdoor dining table with seating, plus a grill for cookouts

→ Private Beach Access: Easy walk to a quiet stretch of shoreline between Wingaersheek and Coffins Beach

→ Parking: Driveway parking for 3 vehicles



★★★ WALKOUT BASEMENT ★★★



→ Ping pong table for indoor fun on rainy or off-beach days

→ Half bathroom

→ Beach gear provided: beach chairs and beach towels, ready to grab on your way out

→ Easy walkout access to the yard and beach path



★★★ THE WINGAERSHEEK EXPERIENCE ★★★



Spend your mornings walking the shoreline, afternoons exploring the sandbars of Wingaersheek Beach, and evenings watching the changing colors over the water from the deck. Whether you're looking for a family beach getaway, a relaxing coastal retreat, or a home base for exploring Cape Ann, this location offers some of the most beautiful scenery on the North Shore.



Guest Access:

Guests will have access to the entire home, both decks, private beach access, and driveway parking throughout their stay.



The home is equipped with a keypad lock for convenient self check-in. Access instructions and your unique entry code will be provided prior to arrival.



A few owner closets and storage areas may remain locked and are not accessible to guests.



Prior to arrival, the Stay Cape Ann team will send your smart lock code and check-in instructions.



The Neighborhood:

Located on Gloucester's highly sought-after Wingaersheek peninsula, this home offers a peaceful coastal setting surrounded by some of Cape Ann's most beautiful beaches and scenery.



A short walk brings you to private beach access located between Wingaersheek Beach and Coffins Beach, providing a quieter alternative to Gloucester's more heavily visited public beaches. Wingaersheek is famous for its wide sandy shoreline, calm waters, and expansive sandbars that emerge at low tide, making it one of the North Shore's most beloved beach destinations.



Whether you're looking for beach days, boating, hiking, or exploring charming coastal towns, this location provides easy access to the very best of Cape Ann.



Getting Around:

A car is recommended for exploring Gloucester and Cape Ann.



Nearby attractions include Wingaersheek Beach, Good Harbor Beach, Rocky Neck Art Colony, the Back Shore, Eastern Point, Stage Fort Park, Downtown Gloucester, and Rockport, all within a short drive.



The Gloucester MBTA Commuter Rail station is approximately 10 minutes away and provides direct service to Boston's North Station, making day trips into the city simple.



Rideshare services are generally available throughout Gloucester, though availability may vary seasonally.



Other Things to Note:

Please enjoy this home respectfully as part of a quiet residential neighborhood. No pets, smoking, or events are permitted. Guests should use care around the deck, stairs, beach access areas, and coastal conditions.



Traveling with little ones? A pack-and-play and high chair may be available upon request. Please let us know before your arrival if you would like either item so we can confirm availability and have it ready for your stay.



Our Stay Cape Ann team lives and works locally. If you need recommendations for beaches, restaurants, fishing charters, or rainy-day activities, we're happy to help.



Interaction with Guests:

We give guests privacy during their stay, but we are available if anything comes up. Our team can be reached by message for questions, recommendations, or support before and during your stay.



Prior to arrival, the Stay Cape Ann team will send your smart lock code and check-in instructions.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0584601070
Property # 5354944vb
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
On-site parties or group events are strictly prohibited
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Gloucester

Located in Gloucester, this holiday home is near the beach. The area's natural beauty can be seen at Wingaersheek Beach and Good Harbor Beach. Maritime Gloucester and Essex Shipbuilding Museum are also worth visiting.
Map
Gloucester, Massachusetts

What's nearby

  • Wingaersheek Beach - 6 min walk - 0.6 km
  • Stage Fort Park - 10 min drive - 8.9 km
  • Half Moon Beach - 12 min drive - 10.0 km
  • Good Harbor Beach - 14 min drive - 12.5 km
  • TD Garden - 58 min drive - 64.0 km

Getting around

  • Manchester Station - 12 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 30 min drive

Restaurants

  • ‪Dunkin' - ‬8 min drive
  • ‪McDonald's - ‬9 min drive
  • ‪The Open Door Food Pantry - ‬9 min drive
  • ‪Starbucks - ‬11 min drive
  • ‪Chipotle Mexican Grill - ‬10 min drive

Frequently asked questions

Is Stay at Wingaersheek pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Stay at Wingaersheek?

As of 21 July 2026, prices found for a 1-night stay for 2 adults at Stay at Wingaersheek on 29 Oct 2026 start from AU$5,410, 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 Stay at Wingaersheek?

On-site parking is available at the property.

What time is check-in at Stay at Wingaersheek?

Check-in begins at 4:00 PM.

What time is check-out at Stay at Wingaersheek?

Checkout is at 11:00 AM.

Where is Stay at Wingaersheek located?

Situated by the sea, this holiday home is 1.4 mi (2.2 km) from Coffins Beach and 1.7 mi (2.7 km) from Wingaersheek Beach. Mount Ann Park and Northeast Hospital Corporation - Addison Gilbert Campus are also within 6 miles (10 km).

About the host

Hosted by Allie

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