Title: Cleveland Circle Vacation Packages 2026 from $714 | Expedia.com [Cleveland Circle Travel Guide](https://expedia.com/Boston-Cleveland-Circle.dx6160076)[Hotels in Cleveland Circle](https://expedia.com/Cleveland-Circle-Boston-Hotels.0-n6160076-0.Travel-Guide-Filter-Hotels)[Flights to Boston](https://expedia.com/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.com/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Car Rentals in Cleveland Circle](https://expedia.com/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 Vacations from $714 ## Book a Hotel + Flight or Car together to unlock savings Photo by Melody Jeng - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Cleveland Circle Vacation Cleveland Circle is calling! Whatever type of break you're planning, you can see and experience the best of this neighborhood with a Cleveland Circle vacation package. When it's time to take in the sights, you'll find a lot of big-name attractions nearby including [Boston College](https://www.expedia.com/Boston-College-Commonwealth.d6092291.Vacation-Attraction), [Agganis Arena](https://www.expedia.com/Agganis-Arena-Allston.d6229782.Vacation-Attraction) and [Paradise Rock Club](https://www.expedia.com/Paradise-Rock-Club-Allston.d553248621533127008.Vacation-Attraction). Visit one, two or more during your trip to Cleveland Circle. Don't just dream it — do it! Secure your perfect Cleveland Circle vacation with Expedia and travel your way. ## The Latest Cleveland Circle Vacation Packages Price found within the past 48 hours. Click for updated prices. ![By the Sea Guests Bed & Breakfast & Suites](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/97cdd647_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### By the Sea Guests Bed & Breakfast & Suites Save 100% on your flight $714 per person May 29 - Jun 3 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.2/10 Wonderful! (185 reviews) Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year! Reviewed on Sep 20, 2025 ![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 Save 100% on your flight $872 per person May 24 - May 27 found 12 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.6/10 Exceptional! (1,004 reviews) Very friendly staff! The location of the hotel is great as well. Reviewed on Mar 13, 2026 ![The Hotel Portsmouth](https://images.trvl-media.com/lodging/1000000/20000/10300/10206/ad86cd83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hotel Portsmouth Downtown Save 100% on your flight $1,199 per person Jun 3 - Jun 10 found 6 hours ago Roundtrip non-stop flight included Los Angeles (LAX) to Boston (BOS) 9.4/10 Exceptional! (1,000 reviews) We loved our stay in the loft. Very romantic and super comfortable. Great location to town and nice breakfast tea and coffee spread in the morning. I’d definitely stay here again. Reviewed on Mar 9, 2026 ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/6c2b250e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge Save 100% on your flight $805 per person May 14 - May 16 found 14 hours ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 9.4/10 Exceptional! (1,000 reviews) Greatest hotel in Cambridge! Reviewed on Mar 13, 2026 ![Life House, Nantucket](https://images.trvl-media.com/lodging/49000000/48530000/48529300/48529240/a9cbc478_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Life House, Nantucket Nantucket Town Save 100% on your flight $1,192 per person May 29 - Jun 3 found 1 day ago Roundtrip flight included Chicago (CHI) to Boston (BOS) 8/10 Very Good! (65 reviews) The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again. Reviewed on Sep 26, 2025 ## 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.com/Boston-Cleveland-Circle.dx6160076) ![Downtown Boston which includes night scenes and a city 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(2,415 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.com/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(3,595 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.com/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 which includes a city, a river or creek and a high rise building](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(1,075 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.com/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 lantern surrounded by lush greenery in Boston during a tranquil afternoon](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(43 area reviews) 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.com/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(330 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.com/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 ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_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 $187 nightly $218 total Mar 22 - Mar 23 Total with taxes and fees 9.2/10 Wonderful! (4,510 reviews) Nice Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=6160076) ![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 $182 nightly $212 total Apr 5 - Apr 6 Total with taxes and fees 8.4/10 Very Good! (3,117 reviews) Second stay here. This is now our go to hotel in Boston. Excellent staff, location, and wonderful lobby/lounge. Can’t wait to return. Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=4215&PinnedHotelID=4215&HadPinnedHotel=true®ionId=6160076) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harborside Inn Of Boston 185 State St Boston MA $169 nightly $197 total Mar 20 - Mar 21 Total with taxes and fees 9.2/10 Wonderful! (6,355 reviews) Can’t say enough good things about this property. Spotless, comfortable, friendly staff, phenomenal location! It’s right at a T stop and we never moved our car for two days. Just perfect! Next to Quincy Market, Faneuil Hall, quick walk to the Aquarium and the North End! Reviewed on Mar 14, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F20%2F2026&endDate=3%2F21%2F2026&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true®ionId=6160076) [See all 4,127 properties in Cleveland Circle](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F15%2F2026&endDate=3%2F16%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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ### Discover the most popular places to visit in Cleveland Circle ![Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts](https://images.trvl-media.com/place/6023384/56814c91-ad37-4ef6-9e12-186349c04e42.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.com/Fenway-Park-FenwayKenmore.d6023384.Vacation-Attraction) ![Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!](https://images.trvl-media.com/place/8136/b9d0e965-3860-4aa0-bd75-1fe651b315dc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Gillette Stadium Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music. [](https://expedia.com/Gillette-Stadium-Boston.d6034500.Vacation-Attraction) ![Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day](https://images.trvl-media.com/place/507377/07fb4e8e-e473-4766-bc75-7dd4f742d04f.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.com/Boston-Common-Beacon-Hill.d507377.Vacation-Attraction) ### Things to do ![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 $23 per adult **92%** of travellers recommend [](https://expedia.com/things-to-do/harvard-university-campus-guided-walking-tour.a1349360.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 $79 per adult **92%** of travellers recommend [](https://expedia.com/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Tour of Historic Fenway Park, America's Most Beloved Ballpark](https://mediaim.expedia.com/localexpert/1349270/b8a279d5-d77b-4fa1-b177-3151a6cdd9f5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tour of Historic Fenway Park, America's Most Beloved Ballpark $45 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/tour-of-historic-fenway-park.a1349270.activity-details) [See all activities in Boston](https://expedia.com/things-to-do/search?rid=6160076) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Hotels near Fenway Park ](https://www.expedia.com/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) - [Hotels near Boston College ](https://www.expedia.com/Boston-College-Hotels.0-l6092291-0.Travel-Guide-Filter-Hotels) - [Hotels near Cleveland Circle Station ](https://www.expedia.com/Cleveland-Circle-Station-Hotels.d6210540.Travel-Guide-Hotels) - [Hotels near Downtown Boston ](https://www.expedia.com/Downtown-Boston-Boston-Hotels.0-n6340396-0.Travel-Guide-Filter-Hotels) - [Hotels near Reservoir Station ](https://www.expedia.com/Reservoir-Station-Hotels.d6210490.Travel-Guide-Hotels) - [Hotels near Chestnut Hill Av. 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