Title: Webster Square Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $764 Expedia.ca [Hotels in Webster Square](https://expedia.ca/Webster-Square-Worcester-Hotels.0-n553248635976477815-0.Travel-Guide-Filter-Hotels)[Flights to Worcester](https://expedia.ca/Cheap-Flights-To-Worcester.d6023336.Travel-Guide-Flights)[Webster Square Car Rentals](https://expedia.ca/Car-Rentals-In-Webster-Square.d553248635976477815.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635976477815/2729aa48-4a10-4b94-9674-e79de44798ef.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Webster Square 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 Webster Square Price found within the past 48 hours. Click for updated prices. ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/d2b7feac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester CA $764 per person Mar 30 - Apr 1 found 15 hours ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 8.4/10 Very Good! (188 reviews) Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available. Reviewed on Nov 10, 2025 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/db81308e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End CA $1,214 per person May 1 - May 6 found 1 hour ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 8.6/10 Excellent! (1,337 reviews) Great staff especially Carmen and Holden very professional and very nice and great customer service. Reviewed on Feb 21, 2026 ![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 $3,560 per person May 1 - May 6 found 1 hour ago Roundtrip non-stop flight included Hamilton (YHM) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) So luxurious with a fabulous staff. I had a very nice room with a terrible view of the top of a parking garage, but I still enjoyed the room! Top-notch service. Brunch options could be a little heartier, I’m a fussy chef! Truly enjoyed my stay! Reviewed on Feb 21, 2026 ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Boston Downtown Boston CA $2,785 per person Apr 18 - Apr 21 found 23 hours ago Roundtrip non-stop flight included Halifax (YHZ) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Friendly staff, clean room Reviewed on Feb 20, 2026 ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Encore Boston Harbor CA $1,194 per person Apr 27 - May 1 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (3,386 reviews) Staying at Encore Boston was an incredible experience from beginning to end. The property is stunning, the atmosphere feels upscale and energetic, and the attention to detail throughout the hotel really stands out. The rooms were spacious, modern, and spotless, with beautiful views and every comfort you could ask for. The service was excellent across the board, and everything—from check-in to dining to the overall ambiance—felt polished and first class. It’s easily one of the most impressive places to stay in the Boston area. I would absolutely come back and highly recommend it to anyone looking for a luxury hotel experience. Reviewed on Feb 24, 2026 ## Where to stay in Webster Square Find the best Webster Square areas and neighborhoods for the activities you enjoy most. [Learn more about Webster Square](https://expedia.ca/Worcester-Webster-Square.dx553248635976477815) ![Worcester Central Business District showing heritage architecture and a city](https://images.trvl-media.com/place/553248635976482380/2aee2088-badf-4d17-8cbd-dbb4485148b4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Worcester Central Business District 4 out of top 10 points of interest in this area 5/5(2 area reviews) If you're spending some time in Worcester Central Business District, DCU Center and Mechanics Hall are top sights worth seeing. [Find hotel + flight trips in Worcester Central Business District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Worcester%20Central%20Business%20District&DestID=553248635976482380&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![very cool space in old buick dealership. great flatbread pizza, great vibe.](https://images.trvl-media.com/place/6023336/052f3b3e-f954-4e2a-8e7d-ebab4c69ae91.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shrewsbury Street Shrewsbury Street might not have many top sights, but Union Station and EcoTarium are two attractions nearby that you can check out. [Find hotel + flight trips in Shrewsbury Street](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Shrewsbury%20Street&DestID=897568218764566528&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) ### Piedmont If you're looking for some top things to see and do in Piedmont and surrounding area, you can visit The Hanover Theatre for the Performing Arts and Mechanics Hall. [Find hotel + flight trips in Piedmont](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Piedmont&DestID=984769317615050752&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Worcester Art Museum aerial view at 55 Salisbury Street in historic downtown Worcester in Massachusetts MA, USA. ](https://images.trvl-media.com/place/897567693610442752/63b37654-a482-4124-a5d2-7c8eca44c94d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Main South 1 out of top 10 points of interest in this area Though Main South might not have many top sights, you can venture to the surrounding area to see attractions like Fitton Baseball Field and Fitton Field. [Find hotel + flight trips in Main South](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Main%20South&DestID=897567693610442752&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) ### Franklin Plantation While Franklin Plantation isn't home to many top sights, EcoTarium and Union Station are some notable places to visit nearby. [Find hotel + flight trips in Franklin Plantation](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Franklin%20Plantation&DestID=553248635976477075&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Webster Square Hotel Deals ![Wellsworth Hotel](https://images.trvl-media.com/lodging/1000000/900000/894300/894252/61dc8b11_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wellsworth Hotel 14 Mechanic St Southbridge MA Fully refundableReserve now, pay when you stay CA $147 CA $164 total Mar 16 - Mar 17 includes taxes & fees 9.2/10 Wonderful! (1,438 reviews) We love the Wellsworth. It’s very clean, friendly attentive employees, heated pool that’s actually warm, indoor basketball court which is cool and unique and tasty restaurant on site, we love the fish n chips! Reviewed on Feb 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=894252&PinnedHotelID=894252&HadPinnedHotel=true®ionId=553248635976477815) ![Embassy Suites by Hilton Boston Marlborough](https://images.trvl-media.com/lodging/1000000/30000/23000/22959/2c252d7a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Boston Marlborough 123 Boston Post Rd W Marlborough MA Fully refundableReserve now, pay when you stay CA $142 CA $159 total Mar 1 - Mar 2 includes taxes & fees 9.2/10 Wonderful! (1,012 reviews) Great hotel and great service Reviewed on Feb 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=22959&PinnedHotelID=22959&HadPinnedHotel=true®ionId=553248635976477815) ![DoubleTree by Hilton Hotel Boston - Westborough](https://images.trvl-media.com/lodging/1000000/20000/18000/17910/4894a4f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Boston - Westborough 5400 Computer Dr Westborough MA Fully refundableReserve now, pay when you stay CA $145 CA $162 total Mar 6 - Mar 7 includes taxes & fees 8.6/10 Excellent! (1,005 reviews) Room was clean. Bar staff was very rude. Reviewed on Feb 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F03%2F2026&endDate=07%2F03%2F2026&selected=17910&PinnedHotelID=17910&HadPinnedHotel=true®ionId=553248635976477815) [See all 377 properties in Webster Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%2F2026®ionId=553248635976477815) 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) ## Frequently asked questions ### How much does a Webster Square vacation package cost? ### How do I get a cheap travel package to Webster Square? ### Where should I stay in Webster Square? ### What are the top hotels in Webster Square? ### How far in advance should I book my Webster Square vacation? ### What does an Expedia Webster Square travel package include? ### What should I know before booking a Webster Square travel package? ### Can I choose my airline with a Webster Square Expedia vacation package? ### If I'm not able to travel, can I cancel my Webster Square vacation package? ### Discover the most popular places to visit in Webster Square ![Old Mill Boathouse rowing sailing paddling center city of port moody Esplanade Ave Rocky Point Park Recreational Pier A rowing lesson on the water Teenagers are engaged in sports club 09.2022 Canada](https://images.trvl-media.com/place/6208520/6b2ab557-f85f-4b69-8bcd-bcce59eae4d1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Regatta Point Park Explore the great outdoors at Regatta Point Park, a lovely green space in Worcester. Attend a sporting event in this family-friendly area. [](https://expedia.ca/Regatta-Point-Park-Worcester.d6208520.Vacation-Attraction) #### DCU Center 4/5(3 reviews) Catch an event at DCU Center during your trip to Worcester. Attend a sporting event in this family-friendly area. [](https://expedia.ca/DCU-Center-Worcester-Central-Business-District.d6070339.Vacation-Attraction) ### Things to do ![1-Hour Axe Throwing in Worcester](https://mediaim.expedia.com/localexpert/48425652/c4dfcf85-b965-46b5-b40d-e6eec47c896c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 1-Hour Axe Throwing in Worcester CA $38 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/1-hour-axe-throwing-in-worcester.a48425652.activity-details) ![Private Walking Tour of the 100th Town in Westborough](https://mediaim.expedia.com/localexpert/46127165/db2e48a9-784b-4e3d-a1cf-39b690382471.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Private Walking Tour of the 100th Town in Westborough CA $55 per traveller [](https://expedia.ca/things-to-do/private-walking-tour-of-the-100th-town-in-westborough.a46127165.activity-details) [See all activities in Worcester](https://expedia.ca/things-to-do/search?rid=553248635976477815) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.