Title: Dudley Square Vacation Packages & Trips 2025 from $524 | Expedia.ca [Hotels in Dudley Square](https://expedia.ca/Dudley-Square-Boston-Hotels.0-n553248635976473876-0.Travel-Guide-Filter-Hotels)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Dudley Square Car Rentals](https://expedia.ca/Car-Rentals-In-Dudley-Square.d553248635976473876.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 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 Dudley Square Price found within the past 48 hours. Click for updated prices. ![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 $684 per person Nov 5 - Nov 8 found 20 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 8.8/10 Excellent! (1,015 reviews) Easy reservations, on-site billing, smooth checkout! Reviewed on Sep 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-08/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=946&paandie=true&dealMarker=md8zQp4YDnq40mCNU-kkOyaSzphfrrZVhyXGmapB8vakQRvEwXQm-PabG_lTyS6Y) ![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 $825 per person Dec 5 - Dec 7 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,028 reviews) This is one of the nicest hotels I’ve stayed in—it’s a beautiful, well-located property with top-notch front desk staff and many thoughtful extras. Reviewed on Sep 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-07/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26146&paandie=true&dealMarker=YZFFsCH7W5ntwwdbTAxd6bqU09T119XimksfAqnqD9uWEUb9ddQ1_gXGHRrZ-CpK) ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/76d84630_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $1,439 per person Oct 31 - Nov 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (159 reviews) Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back! Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-31/2025-11-03/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=911477&paandie=true&dealMarker=JjsjpSLSDcBVJ2gfJ3Wws9IAreBNHsulgblEGv2nl0skzJzLMPpnecoCO8M9W03m) ![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 $851 per person Oct 31 - Nov 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.4/10 Exceptional! (1,005 reviews) I had a lovely stay at this hotel. Very nice atmosphere and close to many restaurants, shopping, and Harvard campus. Although I did not need parking, there was also an on-premise parking lot. Staff were kind and accommodating. My only issue was that the hotel has shows on the 3rd floor and I could hear the music at night from my room on the 4th FL so beware if you are a light sleeper. Otherwise, I would certainly stay here again when in the Cambridge area. Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-31/2025-11-03/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15861&paandie=true&dealMarker=JjsjpSLSDcBVJ2gfJ3Wws9pcl7CEV0ARGU0or0eph_tCBZuLX5EuIsEDS9zPekqd) ![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitney Hotel Beacon Hill CA $1,204 per person Oct 31 - Nov 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (450 reviews) Everything about this place is right! One of the nicest hotels we've ever stayed at. Reviewed on Sep 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-31/2025-11-03/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=29866090&paandie=true&dealMarker=JjsjpSLSDcBVJ2gfJ3Wws_Dzw_y2QNYtpnkAAsve3CpbUhdmBPCFwNU2KdpPzvjr) ## Where to stay in Dudley Square Find the best Dudley Square areas and neighborhoods for the activities you enjoy most. [Learn more about Dudley Square](https://expedia.ca/Boston-Dudley-Square.dx553248635976473876) ![Downtown Boston showing a city and night scenes as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238255-Downtown-Boston.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Boston 4.5/5(193 area reviews) Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here. [Find hotel + flight trips in Downtown Boston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Boston&DestID=6340396&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Back Bay featuring a city, heritage architecture and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/151000/151657-Back-Bay.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Back Bay 1 out of top 10 points of interest in this area 4.5/5(271 area reviews) Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower. [Find hotel + flight trips in Back Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Back%20Bay&DestID=800016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Seaport District featuring a high-rise building, a river or creek and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/151000/151908-South-Boston-Waterfront.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Seaport District 4.5/5(64 area reviews) Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge. [Find hotel + flight trips in Seaport District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Seaport%20District&DestID=6146535&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Beacon Hill which includes landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21013-Beacon-Hill.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Beacon Hill 1 out of top 10 points of interest in this area 5/5(1 area review) Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations. [Find hotel + flight trips in Beacon Hill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beacon%20Hill&DestID=77649&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/476000/476293-North-End-Boston.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North End 1 out of top 10 points of interest in this area 4.5/5(18 area reviews) Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries. [Find hotel + flight trips in North End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20End&DestID=6146485&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Dudley Square Hotel Deals ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Seaport Hotel Boston 1 Seaport Lane, Boston, MA Fully refundableReserve now, pay when you stay CA $313 CA $371 total Sep 21 - Sep 22 includes taxes & fees 9.6/10 Exceptional! (3,423 reviews) "Beautiful property, location and friendly staff" Reviewed on Sep 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=79888&PinnedHotelID=79888&HadPinnedHotel=true®ionId=553248635976473876) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni Boston Hotel at the Seaport 450 Summer Street, Boston, MA Fully refundableReserve now, pay when you stay CA $329 CA $439 total Sep 21 - Sep 22 includes taxes & fees 9/10 Wonderful! (3,987 reviews) "We both said this was probably the nicest (fanciest) hotel we’ve ever stayed at. (And we’ve been. To a lot of fancy hotels). The views, the bathroom, the tiny nook to sit and do your make-up…GORGEOUS! The beds and bedding were heavenly. I already miss them. The coffee shop down stairs has the best ..." Reviewed on Sep 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=553248635976473876) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### citizenM Boston North Station 80-120 Causeway Street, Boston, MA Fully refundableReserve now, pay when you stay CA $260 CA $303 total Sep 21 - Sep 22 includes taxes & fees 9.2/10 Wonderful! (3,767 reviews) "The day we arrived, noticed the comforter, under the cover, had blood stains on it. Gross! Did call down to front desk and they brought us a new one but that should have been caught by the cleaning staff before it was put on our bed!" Reviewed on Sep 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=33870542&PinnedHotelID=33870542&HadPinnedHotel=true®ionId=553248635976473876) [See all 3,751 properties in Dudley Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F09%2F2025&endDate=20%2F09%2F2025®ionId=553248635976473876) 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 Dudley Square vacation package cost? > Live it up in Dudley Square from as little as CA $684. We offer a great selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add some tours or activities to your vacation package. ### How do I get a cheap travel package to Dudley Square? > Bundle, bundle, bundle. Hotels, rental cars and flights — combine whatever you need into a Dudley Square vacation package to save a pile of cash. Score even more deals when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to tailor your vacation your own way. We offer more than 550 air carriers and 1,000,000 properties across the globe, so that everyone has a chance to travel and live out those vacation fantasies. ### Where should I stay in Dudley Square? > Make sightseeing easier by staying someplace near Dudley Square's fantastic attractions. Fenway Park and TD Garden are two visitor favorites. ### How far in advance should I book my Dudley Square vacation? > Get rewarded with the widest variety at the lowest prices by booking your Dudley Square vacation early. Airlines tend to sell flights anywhere up to 12 months prior to departure, so start locking things in ASAP. That being said, Expedia is committed to providing you with the best deals around, so it's always a good time to book your dream vacation! ### What does an Expedia Dudley Square travel package include? > Expedia has all you need to organize your Dudley Square escape, but what goes into your package is your choice. Select from any combination of hotels, rental cars and flights. Looking for some activities or tours to keep you entertained? Once you've made your booking, you can add them too. Whatever your budget, there's a package deal to match your needs. ### What should I know before booking a Dudley Square travel package? > Whether it's adventure or relaxation you're seeking, a Dudley Square vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save! ### Can I choose my airline with a Dudley Square Expedia vacation package? > Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that suit you. ### If I'm not able to travel, can I cancel my Dudley Square vacation package? > If your travel plans in Dudley Square have been upended, it's a relief to know that you can cancel or amend your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. For more information, visit our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105). ### Discover the most popular places to visit in Dudley Square ![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20987-Fenway-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park Catch a game or take a tour at one of America’s most historic and beloved ballparks. [](https://expedia.ca/Fenway-Park-FenwayKenmore.d6023384.Vacation-Attraction) ![Harvard University which includes a city and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21000-Harvard-University.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States. [](https://expedia.ca/Harvard-University-Lower-Allston.d6034936.Vacation-Attraction) ![Boston Common which includes flowers, a garden and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21217-Boston-Common.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind. [](https://expedia.ca/Boston-Common-Beacon-Hill.d507377.Vacation-Attraction) ### Things to do ![Boston CityPASS: Admission to Top 4 Boston Attractions](https://mediaim.expedia.com/localexpert/173116/5d73576c-38be-4337-8351-c85e937f9492.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston CityPASS®: Admission to Top 4 Attractions CA $109 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Boston Harbor Sunset Cruise](https://mediaim.expedia.com/localexpert/1349525/2a83da42-4035-4736-a23f-575189568079.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Harbor Sunset Cruise CA $75 per adult **84%** of travellers recommend [](https://expedia.ca/things-to-do/boston-harbor-sunset-cruise.a1349525.activity-details) ![The top floor of View Boston - 360 degree indoor observation deck ](https://mediaim.expedia.com/localexpert/46312679/72d3435a-7316-42af-bee1-19c21a7437f3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### View Boston Observation Deck Admission Tickets CA $47 per adult **84%** of travellers recommend [](https://expedia.ca/things-to-do/view-boston-observation-deck-admission-tickets.a46312679.activity-details) [See all activities in Boston](https://expedia.ca/things-to-do/search?rid=553248635976473876) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.