Entire home

Stay at Wingaersheek

Vacation home near Wingaersheek Beach in Gloucester

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Photo gallery for Stay at Wingaersheek

Beach nearby
A bedroom with a bed, a ceiling fan, a dresser, and a window.
A kitchen with wooden cabinets, stainless steel appliances, a microwave, and a refrigerator.
A wooden deck with a table and chairs, a green umbrella, and a white railing.
A living room with a brown leather sofa, a wooden coffee table, a patterned rug, and a ceiling fan.

Entire home

271 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a 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

Room options

About the area

Gloucester

Seaside stay .Within 2 miles (3 km) of this Gloucester vacation home, you'll find Wingaersheek Beach and Coffins Beach. Mount Ann Park and Cape Ann Museum are also within 6 miles (10 km).

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Similar properties

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 2,920 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property Registration Number C0584601070

Property is also known as

6a2f2cc22a54770014fbe5de

Frequently asked questions

How close is Stay at Wingaersheek to the airport?

This vacation home is 15.3 mi (30-min drive) away from the Beverly, MA (BVY-Beverly Municipal) airport, the closest popular airport to the property.

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

As of Jul 27, 2026, prices found for a 1-night stay for 2 adults at Stay at Wingaersheek on Jul 30, 2026 start from CA $1,446, excluding 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.

Does Stay at Wingaersheek have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Stay at Wingaersheek to the beach?

This vacation home is 1.7 mi (10-min drive) from Wingaersheek Beach and 7.3 mi (22-min drive) from Good Harbor Beach. Don't forget your sunscreen!

Does Stay at Wingaersheek offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Stay at Wingaersheek?

No, there is no casino at this vacation home.

What time is check-in at Stay at Wingaersheek?

Check-in begins at 4:00 PM.

Is there free parking at Stay at Wingaersheek?

Free parking is not available at this vacation home.

Does Stay at Wingaersheek have a pool?

This vacation home does not have a pool.

Does Stay at Wingaersheek have a spa?

There are no spa services available at this vacation home.

How close is Stay at Wingaersheek to downtown Gloucester?

This vacation home is 3.2 mi away from Gloucester.

Stay at Wingaersheek Reviews