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) --- --- ## Plan a trip to see Wingaersheek Beach Price found within the past 48 hours. Click for updated prices. ![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitney Hotel Beacon Hill CA $1,193 per person Mar 6 - Mar 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (482 reviews) Our second stay there, love it Reviewed on Dec 25, 2025 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $1,656 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) I had a blast at Raffles Reviewed on Jan 12, 2026 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,361 per person Apr 10 - Apr 12 found 15 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Beautiful and great service Reviewed on Jan 15, 2026 ### 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? [](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 [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-01-15&endDate=2026-01-16)[Jan 15 - Jan 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-01-15&endDate=2026-01-16) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-01-16&endDate=2026-01-17)[Jan 16 - Jan 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-01-16&endDate=2026-01-17) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026)[Jan 16 - Jan 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[Jan 23 - Jan 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) ![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 MA [](https://expedia.ca/Gloucester-Hotels-Wingaersheek.h33256297.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 MA [](https://expedia.ca/Gloucester-Hotels-Clean-Waterfront-Classic-Cottage-With-Private-Beach.h46121218.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) ![Sunset Cove: Waterfront at Goose Cove](https://images.trvl-media.com/lodging/45000000/44380000/44370100/44370056/0adb3817_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunset Cove: Waterfront at Goose Cove Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Sunset-Cove-Waterfront-Home-In-Goose-Cove-Section-Of-Gloucester.h44370056.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 MA [](https://expedia.ca/Gloucester-Hotels-Evensong-Oceanview-Retreat-With-Dock.h59079830.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) ![Squam Light: Nestled in the heart of Annisquam](https://images.trvl-media.com/lodging/49000000/48310000/48304700/48304606/70ce2931_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Squam Light: Nestled in the heart of Annisquam Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Squam-Light-A-Newly-Renovated-Cottage.h48304606.Hotel-Information) [See all 613 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. 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