Stay at Wingaersheek | House in Gloucester

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.

Stay at Wingaersheek is located in Gloucester. Stay at Wingaersheek provides accommodation, featuring Wellness Facilities, Air Conditioner, Parking, among other amenities. This House features Air Conditioner, Parking and TV to make your stay a comfortable one.

Stay at Wingaersheek has 3 Bedrooms , 4 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Gloucester has interesting places to visit. If you want to learn more about the House in Gloucester, such as places to visit and things to do nearby, you can check below to learn more.