Title: Wingaersheek Beach in Gloucester - Tours and Activities | Expedia.ca [Wingaersheek Beach Hotels](https://expedia.ca/Wingaersheek-Beach-Hotels.0-l553248621532667334-0.Travel-Guide-Filter-Hotels)[Flights to Gloucester](https://expedia.ca/Cheap-Flights-To-Gloucester.d8008.Travel-Guide-Flights)[Things to do in Gloucester](https://expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities)[Wingaersheek Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Wingaersheek-Beach.d553248621532667334.Car-Rental-Guide)[Gloucester Vacation Packages](https://expedia.ca/Gloucester.d8008.Destination-Travel-Guides) # Wingaersheek Beach Tours and Activities ![Wingaersheek Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531659-wingaersheek-beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531652-wingaersheek-beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531658-wingaersheek-beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531772-wingaersheek-beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531693-wingaersheek-beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Wingaersheek Beach Activities [Gloucester travel guide](https://expedia.ca/Gloucester.dx8008) * * * * * * ### Popular places to visit ![Cape Ann Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531534-cape-ann-museum.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cape Ann Museum You can spend an afternoon exploring the galleries in Cape Ann Museum during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area. [](https://expedia.ca/Cape-Ann-Museum-Gloucester.d553248621532667408.Vacation-Attraction) ![Fishermen's Memorial Monument](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531073-fishermens-memorial-monument.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fishermen's Memorial Monument Learn about the local history of Gloucester with a stop at Fishermen's Memorial Monument. Wander the beautiful beaches and seaside in this family-friendly area. [](https://expedia.ca/Fishermens-Memorial-Monument-Gloucester.d553248621532667320.Vacation-Attraction) ![Pavilion Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/530000/530780-pavilion-beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pavilion Beach Why not spend a lazy afternoon at Pavilion Beach during your trip to Gloucester? While you're in the area, stroll along the seaside. [](https://expedia.ca/Pavilion-Beach-Gloucester.d553248635983990416.Vacation-Attraction) ![Maritime Gloucester](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531237-maritime-gloucester.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Maritime Gloucester You can spend an afternoon studying the exhibits at Maritime Gloucester during your travels in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area. [](https://expedia.ca/Maritime-Gloucester-Gloucester.d553248621532667406.Vacation-Attraction) ![Back Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531021-rockport.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Back Beach Why not spend a lazy afternoon at Back Beach during your trip to Rockport? While you're in the area, stroll along the seaside. [](https://expedia.ca/Back-Beach-Rockport.d553248635983994892.Vacation-Attraction) ![Stage Fort Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531380-stage-fort-park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Stage Fort Park 5/5(1 review) After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander the beautiful beaches and seaside in this family-friendly area. [](https://expedia.ca/Stage-Fort-Park-Gloucester.d553248621532667315.Vacation-Attraction) * * * ## Best Lodging Options Near Wingaersheek Beach ## Check availability on hotels close to Wingaersheek Beach [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-19&endDate=2025-11-20) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-19&endDate=2025-11-20)[Nov 19 - Nov 20](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-19&endDate=2025-11-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-20&endDate=2025-11-21) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-20&endDate=2025-11-21)[Nov 20 - Nov 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2025-11-20&endDate=2025-11-21) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025)[Nov 21 - Nov 23](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025)[Nov 28 - Nov 30](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) ![Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256297/b7f3103a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam Gloucester [](https://expedia.ca/Gloucester-Hotels-Wingaersheek.h33256297.Hotel-Information) ![Rockport Inn And Suites](https://images.trvl-media.com/lodging/3000000/2810000/2803800/2803719/1c83e728_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rockport Inn And Suites 183 Main Street Rockport MA [](https://expedia.ca/Rockport-Hotels-Rockport-Inn-And-Suites.h2803719.Hotel-Information) ![Elegant Gloucester Beach Getaway With Ocean Views!](https://images.trvl-media.com/lodging/95000000/94490000/94480300/94480246/w557h394x3y0-59dd60a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elegant Gloucester Beach Getaway With Ocean Views! Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Elegant-Gloucester-Beach-Getaway-With-Ocean-Views.h94480246.Hotel-Information) ![Wingaerchic: Woodsy retreat in West Gloucester](https://images.trvl-media.com/lodging/65000000/64760000/64754600/64754528/78ba5d09_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingaerchic: Woodsy retreat in West Gloucester Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Wingaerchic-A-Hidden-Retreat-Near-Gloucesters-Sandy-Wingaersheek-Beach.h64754528.Hotel-Information) ![Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive](https://images.trvl-media.com/lodging/33000000/32040000/32034100/32034014/fc695ffe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Waterfront-Living-W-Stunning-Views.h32034014.Hotel-Information) ![Clean Waterfront Classic Cottage with Private Beach](https://images.trvl-media.com/lodging/47000000/46130000/46121300/46121218/614dd755_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clean Waterfront Classic Cottage with Private Beach Gloucester [](https://expedia.ca/Gloucester-Hotels-Clean-Waterfront-Classic-Cottage-With-Private-Beach.h46121218.Hotel-Information) ![Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family ](https://images.trvl-media.com/lodging/34000000/33650000/33642800/33642765/0d02138b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Wingaersheek.h33642765.Hotel-Information) ![Evensong: Oceanview Retreat with Dock](https://images.trvl-media.com/lodging/60000000/59080000/59079900/59079830/276f197c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Evensong: Oceanview Retreat with Dock Gloucester [](https://expedia.ca/Gloucester-Hotels-Evensong-Oceanview-Retreat-With-Dock.h59079830.Hotel-Information) ![Oceanfront Dock Escape ~ Kayaks & Paddleboards](https://images.trvl-media.com/lodging/112000000/111760000/111754800/111754760/9bb00a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceanfront Dock Escape ~ Kayaks & Paddleboards Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Waterfront-Escape-Kayaks.h111754760.Hotel-Information) [See all 607 properties in Wingaersheek Beach](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248621532667334) 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [3 Star Hotels in Gloucester](https://www.expedia.ca/3Star-Gloucester-Hotels.s30-0-d8008.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Cheap-Hotels.0-n553248635975257320-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Historic-Hotel.0-n553248635975257320-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Honeymoon-Hotels.0-n553248635975257320-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Annisquam](https://www.expedia.ca/Annisquam-Gloucester-Hotels-Pet-Friendly-Hotel.0-n553248635975257320-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Annisquam Hotels](https://www.expedia.ca/Annisquam-Gloucester-Hotels.0-n553248635975257320-0.Travel-Guide-Filter-Hotels) - 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[Flights to Gloucester](https://www.expedia.ca/Cheap-Flights-To-Gloucester.d8008.Travel-Guide-Flights) - [Flights from Columbus to North Shore](https://www.expedia.ca/lp/flights/178251/6047672/columbus-to-north-shore) - [Flights from Dublin to North Shore](https://www.expedia.ca/lp/flights/178256/6047672/dublin-to-north-shore) - [Flights from Kansas City to North Shore](https://www.expedia.ca/lp/flights/178273/6047672/kansas-city-to-north-shore) - [Flights from Nashville to North Shore](https://www.expedia.ca/lp/flights/178291/6047672/nashville-to-north-shore) - [Flights from New Orleans to North Shore](https://www.expedia.ca/lp/flights/178292/6047672/new-orleans-to-north-shore) - [Flights from Phoenix to North Shore](https://www.expedia.ca/lp/flights/178298/6047672/phoenix-to-north-shore) - [Flights from Salt Lake City to North Shore](https://www.expedia.ca/lp/flights/178302/6047672/salt-lake-city-to-north-shore) - [Flights from Toronto to North Shore](https://www.expedia.ca/lp/flights/178314/6047672/toronto-to-north-shore) - [Flights from Pittsburgh to North Shore](https://www.expedia.ca/lp/flights/601717/6047672/pittsburgh-to-north-shore) - [Flights from Winnipeg to North Shore](https://www.expedia.ca/lp/flights/6141041/6047672/winnipeg-to-north-shore) - [Andover Country Club](https://www.expedia.ca/Andover-Country-Club-Andover.d6263084.Vacation-Attraction) - [Beverly Vacations](https://www.expedia.ca/Beverly.d6445.Destination-Travel-Guides) - [Crane Beach](https://www.expedia.ca/Crane-Beach-Massachusetts.d553248621532667333.Vacation-Attraction) - [Gloucester Vacations](https://www.expedia.ca/Gloucester.d8008.Destination-Travel-Guides) - [Visit Gloucester](https://www.expedia.ca/Gloucester.dx8008) - [Good Harbor Beach](https://www.expedia.ca/Good-Harbor-Beach-Gloucester.d553248621532667409.Vacation-Attraction) - [Greenwood Farm](https://www.expedia.ca/Greenwood-Farm-Ipswich.d553248621532667330.Vacation-Attraction) - [Hammond Castle](https://www.expedia.ca/Hammond-Castle-Gloucester.d6092287.Vacation-Attraction) - [Lynn Vacations](https://www.expedia.ca/Lynn.d8437.Destination-Travel-Guides) - [Magnolia Vacations](https://www.expedia.ca/Magnolia.d6340902.Destination-Travel-Guides) - [Marblehead Light](https://www.expedia.ca/Marblehead-Light-Boston.d6091765.Vacation-Attraction) - [North Shore Vacations](https://www.expedia.ca/North-Shore.d6047672.Destination-Travel-Guides) - [Oldies Marketplace](https://www.expedia.ca/Oldies-Marketplace-Newburyport.d553248621561735335.Vacation-Attraction) - [Penguin Park](https://www.expedia.ca/Penguin-Park-Andover.d6263078.Vacation-Attraction) - [Philips Academy](https://www.expedia.ca/Philips-Academy-Andover.d6070261.Vacation-Attraction) - [Revere Beach](https://www.expedia.ca/Revere-Beach-Boston.d6171946.Vacation-Attraction) - [Salem Wax Museum](https://www.expedia.ca/Salem-Wax-Museum-Boston.d6262942.Vacation-Attraction) - [Salem Witch Museum](https://www.expedia.ca/Salem-Witch-Museum-Boston.d6091753.Vacation-Attraction) - [Salem Witch Trials Memorial](https://www.expedia.ca/Salem-Witch-Trials-Memorial-Boston.d553248621532667447.Vacation-Attraction) - [Salem Vacations](https://www.expedia.ca/Salem.d6600.Destination-Travel-Guides) - [Salisbury Beach State Reservation](https://www.expedia.ca/Salisbury-Beach-State-Reservation-Salisbury.d553248621532667399.Vacation-Attraction) - [Singing Beach](https://www.expedia.ca/Singing-Beach-Manchester-by-the-Sea.d553248621561735338.Vacation-Attraction) - [South Hamilton Vacations](https://www.expedia.ca/South-Hamilton.d6135804.Destination-Travel-Guides) - [Stoneham Vacations](https://www.expedia.ca/Stoneham.d162713.Destination-Travel-Guides) - [Straightsmouth Island Lighthouse](https://www.expedia.ca/Straightsmouth-Island-Lighthouse-Rockport.d553248621532667411.Vacation-Attraction) - [The Lynn Auditorium](https://www.expedia.ca/The-Lynn-Auditorium-Boston.d553248621532667139.Vacation-Attraction) - [Wakefield Vacations](https://www.expedia.ca/Wakefield.d7519.Destination-Travel-Guides) - [Water Park of New England](https://www.expedia.ca/Water-Park-Of-New-England-Boston.d553248621532667299.Vacation-Attraction) - [Waterfront Promenade Park](https://www.expedia.ca/Waterfront-Promenade-Park-Newburyport.d6274378.Vacation-Attraction) - [Witch Dungeon Museum](https://www.expedia.ca/Witch-Dungeon-Museum-Boston.d6262921.Vacation-Attraction) - [Witch History Museum](https://www.expedia.ca/Witch-History-Museum-Boston.d6262930.Vacation-Attraction) - [Avis Rental Cars in Gloucester](https://www.expedia.ca/Avis-Car-Rentals-In-Gloucester.d8008-c41.Car-Rental-Guide-Suppliers) - [Car rentals near North Shore](https://www.expedia.ca/Car-Rentals-In-North-Shore.d6047672.Car-Rental-Guide) - [Top Rent a Car Rental Cars in North Shore](https://www.expedia.ca/Top-Rent-A-Car-Car-Rentals-In-North-Shore.d6047672-c1028.Car-Rental-Guide-Suppliers) - [Gloucester Vacation Rentals](https://www.expedia.ca/Gloucester-Vacation-Rentals.d8008.Travel-Guide-VacationRentals) - [North Shore Vacation Rentals](https://www.expedia.ca/North-Shore-Vacation-Rentals.d6047672.Travel-Guide-VacationRentals) - [Things to do in Gloucester](https://www.expedia.ca/Things-To-Do-In-Gloucester.d8008.Travel-Guide-Activities) - [Things to do in North Shore](https://www.expedia.ca/Things-To-Do-In-North-Shore.d6047672.Travel-Guide-Activities)