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 featuring rugged coastline](https://images.trvl-media.com/place/553248621532667334/f266a0de-f3f4-41b3-a53e-7e5aa912d50e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach featuring rugged coastline](https://images.trvl-media.com/place/553248621532667334/f266a0de-f3f4-41b3-a53e-7e5aa912d50e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach showing rugged coastline and general coastal views](https://images.trvl-media.com/place/553248621532667334/3f4dc30d-8bfb-41dc-a198-f0ce79c08d41.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach featuring rugged coastline and general coastal views](https://images.trvl-media.com/place/553248621532667334/ad6416dc-d545-4ec1-a00b-12a8e2b9ae93.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Wingaersheek Beach featuring general coastal views and rugged coastline](https://images.trvl-media.com/place/553248621532667334/f1de2883-c735-4623-a439-994d51275765.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. ![Embassy Suites by Hilton Boston Waltham](https://images.trvl-media.com/lodging/1000000/20000/14900/14808/fd912bfb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Boston Waltham CA $1,105 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8/10 Very Good! (2,605 reviews) Very clean very nice big comfy room Reviewed on Feb 19, 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 $4,176 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![Studio Allston Hotel](https://images.trvl-media.com/lodging/23000000/22760000/22757100/22757092/a522d616_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Studio Allston Hotel Brighton CA $1,393 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.6/10 Excellent! (1,175 reviews) Room had basics. Bed was stiff and there was a sharp metal frame that I cut my leg on. The exterior patio appeared unmaintained but looked cool. Reviewed on Feb 22, 2026 ### Popular places to visit ![Cape Ann Museum which includes outdoor art](https://images.trvl-media.com/place/553248621532667408/553eb2bd-2446-499f-9419-a1ac4b2e9035.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 showing a statue or sculpture](https://images.trvl-media.com/place/553248621532667320/6fe2b871-c9c0-45e2-9e7c-9d91e17dfce2.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 showing a sandy beach and a coastal town](https://images.trvl-media.com/place/553248635983990416/7eb20391-a86a-47da-8226-b6f3e6fee445.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 as well as a small group of people](https://images.trvl-media.com/place/553248621532667406/1591d05f-3f58-412a-a304-a1272214e614.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 showing general coastal views](https://images.trvl-media.com/place/553248635983994892/2599448a-ea1b-4d17-acf8-c0e4fc148880.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 showing a coastal town and a bay or harbor](https://images.trvl-media.com/place/553248621532667315/f43b5211-3c4e-417f-ac03-06c6c9d907dd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Stage Fort Park 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=2026-02-23&endDate=2026-02-24)[Feb 23 - Feb 24](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-02-23&endDate=2026-02-24) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-02-24&endDate=2026-02-25)[Feb 24 - Feb 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=2026-02-24&endDate=2026-02-25) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026)[Mar 6 - Mar 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621532667334&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026) ![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) ![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) ![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) ![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) ![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) ![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) ![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) ![Steps to Wingaersheek's Private 1.5 Mile White Dune Beach](https://images.trvl-media.com/lodging/37000000/36310000/36308400/36308372/c95c7083_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Steps to Wingaersheek's Private 1.5 Mile White Dune Beach Gloucester MA [](https://expedia.ca/Gloucester-Hotels-Steps-To-Wingaersheeks-15-Mile-White-Dune-Private-Beach.h36308372.Hotel-Information) [See all 609 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. 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[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) - 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[Things to do in North Shore ](https://www.expedia.ca/Things-To-Do-In-North-Shore.d6047672.Travel-Guide-Activities)