Title: Cleveland Circle Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $755 Expedia.ca [Hotels in Cleveland Circle](https://expedia.ca/Cleveland-Circle-Boston-Hotels.0-n6160076-0.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)[Cleveland Circle Car Rentals](https://expedia.ca/Car-Rentals-In-Cleveland-Circle.d6160076.Car-Rental-Guide) ![](https://images.trvl-media.com/place/660/8ffbd804-9bdd-4269-bc67-e05fcf65a0ab.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cleveland Circle Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Melody Jeng - ## 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 Cleveland Circle Price found within the past 48 hours. Click for updated prices. ![The Wylie Inn and Conference Center at Endicott College](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/e13dffe5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wylie Inn and Conference Center at Endicott College CA $755 per person Apr 2 - Apr 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.2/10 Wonderful! (1,111 reviews) Clean. Spacious room. Comfortable bed. Great location. Reviewed on Feb 7, 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 $2,266 per person Apr 2 - Apr 8 found 1 day 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 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 $1,112 per person Apr 23 - Apr 26 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you Reviewed on Feb 3, 2026 ## Where to stay in Cleveland Circle Find the best Cleveland Circle areas and neighborhoods for the activities you enjoy most. [Learn more about Cleveland Circle](https://expedia.ca/Boston-Cleveland-Circle.dx6160076) ![Downtown Boston showing a city and night scenes as well as a small group of people](https://images.trvl-media.com/place/6340396/147aba27-8694-4725-895d-0beb6077ab67.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://images.trvl-media.com/place/800016/ecea0c09-2ade-4d56-b74d-09ed645f6ef5.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://images.trvl-media.com/place/6146535/5487f5d9-6748-43ca-b7bd-e50e2e9d2a27.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://images.trvl-media.com/place/77649/9741c4ac-c840-46d1-b907-3b388935c98f.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) ![Boston Harbor which includes performance art, music and a bay or harbor](https://images.trvl-media.com/place/553248634340925170/190102c5-6ec7-4f3d-9631-9a7f002e9676.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) ## Cleveland Circle Hotel Deals ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Boston Park Plaza 50 Park Plaza Boston MA Fully refundableReserve now, pay when you stay CA $140 CA $219 total Feb 22 - Feb 23 includes taxes & fees 8.2/10 Very Good! (3,103 reviews) Room Nice and clean, but small. Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true®ionId=6160076) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harborside Inn Of Boston 185 State St Boston MA CA $145 CA $169 total Feb 24 - Feb 25 includes taxes & fees 9.2/10 Wonderful! (6,220 reviews) Excellent Hotel in a great location with a subway station right next to the front entrance. Would highly recommend Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true®ionId=6160076) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Revolution Hotel 40 Berkeley Street Boston MA Fully refundableReserve now, pay when you stay CA $118 CA $138 total Mar 10 - Mar 11 includes taxes & fees 9/10 Wonderful! (2,451 reviews) I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ... Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=30080227&PinnedHotelID=30080227&HadPinnedHotel=true®ionId=6160076) [See all 4,071 properties in Cleveland Circle](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F02%2F2026&endDate=15%2F02%2F2026®ionId=6160076) 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 Cleveland Circle vacation package cost? ### How do I get a cheap travel package to Cleveland Circle? ### How far in advance should I book my Cleveland Circle vacation? ### What does an Expedia Cleveland Circle travel package include? ### What should I know before booking a Cleveland Circle travel package? ### Can I choose my airline with a Cleveland Circle Expedia vacation package? ### If I'm not able to travel, can I cancel my Cleveland Circle vacation package? ### Discover the most popular places to visit in Cleveland Circle ![Boston Common which includes flowers, a garden and landscape views](https://images.trvl-media.com/place/507377/07fb4e8e-e473-4766-bc75-7dd4f742d04f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common 4.5/5(518 reviews) 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) ![Boston's Zakim Bridge](https://images.trvl-media.com/place/6070137/28b26e99-a684-4d32-8b62-4180d99b863d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### TD Garden 4.5/5(240 reviews) Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area. [](https://expedia.ca/TD-Garden-West-End.d6070137.Vacation-Attraction) ![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://images.trvl-media.com/place/6023384/56814c91-ad37-4ef6-9e12-186349c04e42.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park 4.5/5(305 reviews) 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) ### Things to do ![Boston Hop-On Hop-Off Trolley Tour](https://mediaim.expedia.com/localexpert/172982/6f42f390-62da-409c-a976-5a931abb154f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Old Town Trolley Hop-on Hop-Off City Tour CA $72 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/boston-old-town-trolley-hop-on-hop-off-city-tour.a172982.activity-details) ![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 $108 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Zac tells a story about the John Harvard statue](https://mediaim.expedia.com/localexpert/1349360/d8650b03-f74e-4c81-8957-837ce0090701.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Campus Guided Walking Tour CA $31 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/harvard-university-campus-guided-walking-tour.a1349360.activity-details) [See all activities in Boston](https://expedia.ca/things-to-do/search?rid=6160076) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.