Title: Dudley Vacation Packages & Trips 2026 from CA $856 | Expedia.ca [Hotels in Dudley](https://expedia.ca/Dudley-Hotels.d8952.Travel-Guide-Hotels)[Vacation Rentals in Dudley](https://expedia.ca/Dudley-Vacation-Rentals.d8952.Travel-Guide-VacationRentals)[Flights to Dudley](https://expedia.ca/Cheap-Flights-To-Dudley.d8952.Travel-Guide-Flights)[Dudley Car Rentals](https://expedia.ca/Car-Rentals-In-Dudley.d8952.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) # Dudley 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 #### Your Dudley Vacation Cuisine, art, entertainment and more … There's a whole lot to discover with a Dudley vacation package. And with the ability to customize your city adventure, it's guaranteed to be one that's tough to forget. [Indian Ranch](https://www.expedia.ca/Indian-Ranch-Webster.d553248621532666009.Vacation-Attraction), [Lake Chaubunagungamaug](https://www.expedia.ca/Lake-Chaubunagungamaug-Webster.d553248635976196323.Vacation-Attraction) and [Lake Webster](https://www.expedia.ca/Lake-Webster-Webster.d553248621532666007.Vacation-Attraction) are just some of the many attractions you'll want to explore during your trip to Dudley. Whoever you're escaping with and whatever your bank balance, your ultimate Dudley vacation is just a few clicks away with Expedia. ## Top Dudley Vacation Deals 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 19 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 ## Ready to book your vacation to Dudley? Choose your dates ## Dudley 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 Feb 9 - Feb 10 includes taxes & fees 9/10 Wonderful! (1,409 reviews) Staff was great room was very clean Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=894252&PinnedHotelID=894252&HadPinnedHotel=true®ionId=8952) ![Hilton Garden Inn Worcester](https://images.trvl-media.com/lodging/2000000/1480000/1478200/1478175/82c11218_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Worcester 35 Major Taylor Boulevard Worcester MA Fully refundableReserve now, pay when you stay CA $173 CA $198 total Feb 17 - Feb 18 includes taxes & fees 7.8/10 Good! (1,003 reviews) Lovely staff, great pool area with hot tub Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=1478175&PinnedHotelID=1478175&HadPinnedHotel=true®ionId=8952) ![AC Hotel by Marriott Worcester](https://images.trvl-media.com/lodging/21000000/20960000/20958800/20958776/2f014c1c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AC Hotel by Marriott Worcester 125 Front St Worcester MA Fully refundableReserve now, pay when you stay CA $207 CA $236 total Feb 15 - Feb 16 includes taxes & fees 9.2/10 Wonderful! (1,001 reviews) Clean, spacious rooms, nice restaurant next door. Good customer service Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=20958776&PinnedHotelID=20958776&HadPinnedHotel=true®ionId=8952) [See all 352 properties in Dudley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=8952) 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) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app