Wingaersheek Beach

A rocky shoreline with large boulders and a distant view of houses and trees.
A rocky shoreline with large boulders and calm water.
A coastal landscape with a large white house surrounded by rocks and greenery.
A rocky beach with large boulders and a distant view of a town with houses and trees.
A coastal beach with rocky outcrops, calm water, and houses on a hillside.

Things to do

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

€15
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

€36
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

€19
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
Salem Witch Trials Self-Guided Audio Tour

Salem Witch Trials Self-Guided Walking Tour

€15
per traveller
90% of travellers recommend
Salem Witch Trials Self-Guided Walking Tour
Within A Witching Hour Spellcasting Ticket

Within A Witching Hour Spellcasting Ticket

€18
per adult
100% of travellers recommend
Within A Witching Hour Spellcasting Ticket
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

€15
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
See all activities in Gloucester
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was €719, price is now €514 per person
€514
per person
22 Nov - 25 Nov
found 6 hours ago
Return direct flight included
Calgary (YYC) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €1,349, price is now €789 per person
€789
per person
22 Nov - 25 Nov
found 6 hours ago
Return direct flight included
Calgary (YYC) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Everyone from outside arrival and beyond were helpful, friendly and welcoming.

Reviewed on 22 Oct 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was €1,625, price is now €996 per person
€996
per person
1 Dec - 6 Dec
found 6 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The room and property met my expectations. Given the angle of the building to the water I didn't think there would be much of a view but we got lucky and even from the SE facing side of building 3 we could watch sailboats coming and going from the Boston channel.

Reviewed on 22 Oct 2026

Stay near popular Wingaersheek Beach attractions

Wingaersheek Beach

9.4/10 (83 reviews)
Why not spend a care-free afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.
See properties

Top Hotel Deals

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

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

Gloucester MA
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
Elegant Gloucester Beach Getaway with Ocean Views!

Elegant Gloucester Beach Getaway with Ocean Views!

Gloucester MA
Elegant Gloucester Beach Getaway with Ocean Views!
Rockport Inn And Suites

Rockport Inn And Suites

2.5 out of 5
183 Main Street Rockport MA
Rockport Inn And Suites
Gull's Nest - Ocean Views from the Living Room

Gull's Nest - Ocean Views from the Living Room

Gloucester MA
Gull's Nest - Ocean Views from the Living Room
Clean Waterfront Classic Cottage with Private Beach

Clean Waterfront Classic Cottage with Private Beach

Gloucester MA
Clean Waterfront Classic Cottage with Private Beach
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

Gloucester MA
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
Sunset Cove: Waterfront living on the Annisquam River

Sunset Cove: Waterfront living on the Annisquam River

Gloucester MA
Sunset Cove: Waterfront living on the Annisquam River
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

Gloucester MA
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family

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

Gloucester MA
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
See all 638 properties in Wingaersheek Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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