Title: Downtown Gloucester Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,336 Expedia.ca [Downtown Gloucester Travel Guide](https://expedia.ca/Gloucester-Downtown-Gloucester.dx988950093891813376)[Hotels in Downtown Gloucester](https://expedia.ca/Downtown-Gloucester-Hotels.d988950093891813376.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)[Downtown Gloucester Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Gloucester.d988950093891813376.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) # Downtown 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 Downtown Gloucester Price found within the past 48 hours. Click for updated prices. ![The Westin Boston Seaport District](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/b920b61e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Boston Seaport District Seaport District CA $1,336 per person Jun 15 - Jun 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.2/10 Wonderful! (2,404 reviews) Great hotel from start to finish. Highly recommend Reviewed on Mar 22, 2026 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/ee935931_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End CA $1,762 per person Jun 15 - Jun 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 8.6/10 Excellent! (1,395 reviews) Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure Reviewed on Mar 30, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $3,918 per person Jun 15 - Jun 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.6/10 Exceptional! (238 reviews) The photos doesn’t give this place justice. Reviewed on Mar 24, 2026 ![The Inn at Hastings Park, Relais & Chateaux - Boston](https://images.trvl-media.com/lodging/8000000/7990000/7980700/7980601/8dcd0e80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Hastings Park, Relais & Chateaux - Boston CA $1,673 per person Jun 13 - Jun 17 found 17 hours ago Roundtrip non-stop flight included Toronto (YTZ) to Boston (BOS) 9.6/10 Exceptional! (252 reviews) Excellent experience- clean and very helpful staff Reviewed on Mar 9, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $3,521 per person Jun 15 - Jun 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products. Reviewed on Mar 29, 2026 ## Where to stay in Downtown Gloucester Find the best Downtown Gloucester areas and neighborhoods for the activities you enjoy most. [Learn more about Downtown Gloucester](https://expedia.ca/Gloucester-Downtown-Gloucester.dx988950093891813376) ![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) ### East Gloucester 3 out of top 10 points of interest in this area If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing. [Find hotel + flight trips in East Gloucester](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Gloucester&DestID=988950575026716672&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) ![Magnolia](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 1 out of top 10 points of interest in this area 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) ## Downtown Gloucester Hotel Deals ![Beauport Hotel Gloucester](https://images.trvl-media.com/lodging/16000000/15380000/15379900/15379825/70af0ced_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beauport Hotel Gloucester 55 Commercial Street Gloucester MA CA $312 CA $348 total Apr 2 - Apr 3 includes taxes & fees 9.6/10 Exceptional! (938 reviews) Rooms are not sound proof. Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=15379825&PinnedHotelID=15379825&HadPinnedHotel=true®ionId=988950093891813376) ![Harborview Inn](https://images.trvl-media.com/lodging/10000000/9730000/9729300/9729289/8160d750_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harborview Inn 71 Western Avenue Gloucester MA CA $263 CA $294 total Apr 2 - Apr 3 includes taxes & fees 9.6/10 Exceptional! (319 reviews) Parking was very easy. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=9729289&PinnedHotelID=9729289&HadPinnedHotel=true®ionId=988950093891813376) ![The Highliner Hotel](https://images.trvl-media.com/lodging/123000000/122190000/122189000/122188981/b7e2c326_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Highliner Hotel 108 Main St Gloucester MA CA $245 CA $492 total Apr 2 - Apr 3 includes taxes & fees 10/10 Exceptional! (1 review) Quiet and the staff was really friendly. Great location and the hotel is spotless. Reviewed on Jan 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=122188981&PinnedHotelID=122188981&HadPinnedHotel=true®ionId=988950093891813376) [See all 1,152 properties in Downtown Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=988950093891813376) 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) ### 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 $21 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/c77d1e46-92e0-4624-910e-8f6f89d968d2.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 Self-Guided Audio Tour Bundle: 10+ Tours](https://mediaim.expedia.com/localexpert/5247794/0163ce8b-bcb9-433e-bb84-fa4c7a677dc8.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=988950093891813376) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.