Title: East Gloucester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $856 Expedia.ca [East Gloucester Travel Guide](https://expedia.ca/Gloucester-East-Gloucester.dx988950575026716672)[Hotels in East Gloucester](https://expedia.ca/East-Gloucester-Hotels.d988950575026716672.Travel-Guide-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)[East Gloucester Car Rentals](https://expedia.ca/Car-Rentals-In-East-Gloucester.d988950575026716672.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # East Gloucester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in East Gloucester Price found within the past 48 hours. Click for updated prices. ![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 $856 per person Mar 18 - Mar 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.6/10 Excellent! (1,175 reviews) Staff was friendly. Room was clean Reviewed on Feb 5, 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 $1,643 per person Apr 29 - May 2 found 17 hours 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 ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge CA $1,711 per person Mar 18 - Mar 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.4/10 Exceptional! (1,003 reviews) Room very well appointed and gym was the stand out Reviewed on Jan 25, 2026 ![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/e477f850_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree Suites by Hilton Hotel Boston - Cambridge Allston CA $887 per person Mar 18 - Mar 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.8/10 Excellent! (1,000 reviews) Staff was great we were treated with warm chocolate chip cookies. but Expedia told us breakfast was included and that was a lie Reviewed on Feb 2, 2026 ## Where to stay in East Gloucester Find the best East Gloucester areas and neighborhoods for the activities you enjoy most. [Learn more about East Gloucester](https://expedia.ca/Gloucester-East-Gloucester.dx988950575026716672) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Gloucester 2 out of top 10 points of interest in this area While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Capt Bill & Sons Whale Watch. [Find hotel + flight trips in Downtown Gloucester](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Gloucester&DestID=988950093891813376&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Annisquam Light, Gloucester, Massachusetts, USA; Shutterstock ID 161751743](https://images.trvl-media.com/place/553248635975257320/e8be7e48-f2a6-42d0-b81c-dd477a50772c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Annisquam While Annisquam might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wingaersheek Beach and Plum Cove Beach. [Find hotel + flight trips in Annisquam](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Annisquam&DestID=553248635975257320&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Beautiful place to walk and enjoy the views. This foggy noon created the atmosphere of an unreal world.](https://images.trvl-media.com/place/8008/5147534c-4020-4b19-8522-3f89d8edc342.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnolia Nestled in Gloucester, this small village boasts its own library, restaurants, and shops. Enjoy Gray Beach at Coolidge Reservation or take in scenic views of Kettle Cove at Surf Park. [Find hotel + flight trips in Magnolia](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnolia&DestID=6340902&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rocky Neck If you're spending some time in Rocky Neck, Rocky Neck Art Colony and Bryan Gallery are top sights worth seeing. [Find hotel + flight trips in Rocky Neck](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Rocky%20Neck&DestID=988950237638844416&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## East Gloucester Hotel Deals ![Long Beach Suites](https://images.trvl-media.com/lodging/92000000/91560000/91553600/91553529/e3c9fce6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Long Beach Suites 28 Rockport Rd Gloucester MA 9.2/10 Wonderful! (61 reviews) It's amazing & very private, has everything you could need! Reviewed on Jan 3, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=91553529&PinnedHotelID=91553529&HadPinnedHotel=true®ionId=988950575026716672) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=91553529&PinnedHotelID=91553529&HadPinnedHotel=true®ionId=988950575026716672) ![The Vista](https://images.trvl-media.com/lodging/10000000/9480000/9480000/9479946/1d8ac3d9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Vista 22 Thatcher Rd. Gloucester MA 9.4/10 Exceptional! (418 reviews) Loved Anna at breakfast and watching the sunrise. It’s heaven here. Want a time share!! Reviewed on Oct 27, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=9479946&PinnedHotelID=9479946&HadPinnedHotel=true®ionId=988950575026716672) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=9479946&PinnedHotelID=9479946&HadPinnedHotel=true®ionId=988950575026716672) ![Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach](https://images.trvl-media.com/lodging/111000000/110900000/110893900/110893889/445876ef_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach Gloucester MA 6.6/10 (3 reviews) Everything about the experience of this stay was beyond my expectations. Let's start with the Communication between me and the property manager. Couldn't have asked for better. Any time I had a question I typically heard back within an hour. The home itself was incredible. When they say this place ... Reviewed on Feb 1, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=110893889&PinnedHotelID=110893889&HadPinnedHotel=true®ionId=988950575026716672) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=110893889&PinnedHotelID=110893889&HadPinnedHotel=true®ionId=988950575026716672) [See all 1,152 properties in East Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=988950575026716672) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in East Gloucester ![Good Harbor Beach which includes a sunset and a coastal town](https://images.trvl-media.com/place/553248621532667409/f7438f55-8c31-4a48-8a51-cf3f9e28dca7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Good Harbor Beach Why not spend a carefree afternoon at Good Harbor Beach during your travels in Gloucester? Wander the waterfront or discover the area's sunrises. [](https://expedia.ca/Good-Harbor-Beach-East-Gloucester.d553248621532667409.Vacation-Attraction) ### Things to do ![Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour](https://mediaim.expedia.com/localexpert/823381/04e76f58-c1d8-4768-84d0-bcae3ea6e07f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cape Ann Harbor: Self-Guided Driving Audio Tour CA $23 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/cape-ann-harbor-self-guided-driving-audio-tour.a823381.activity-details) ![Cape Ann Self-Guided Driving Tour in Gloucester and Rockport](https://mediaim.expedia.com/localexpert/3060314/25d71e0c-f1f2-40ad-9b58-41d96a7c86e7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cape Ann Self-Guided Driving Tour in Gloucester and Rockport CA $23 per traveller **80%** of travellers recommend [](https://expedia.ca/things-to-do/cape-ann-self-guided-driving-tour-in-gloucester-and-rockport.a3060314.activity-details) ![Massachusetts Highlights: Freedom Trail, Salem & More Tour](https://mediaim.expedia.com/localexpert/5247794/991bb3ab-4de4-47da-8b84-5a4e09a0b2d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours CA $68 per adult [](https://expedia.ca/things-to-do/massachusetts-self-guided-audio-tour-bundle-10-tours.a5247794.activity-details) [See all activities in Gloucester](https://expedia.ca/things-to-do/search?rid=988950575026716672) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.