Cleveland Circle Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Cleveland Circle
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
Back Bay
CA $2,895
per person
Oct 30 - Nov 4
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (294 reviews)
Boutique hotel feel . It was an excellent stay, staff is awesome, location is great. Those sheets are heavenly, I have been told they are French.
Reviewed on Aug 24, 2026
The Langham, Boston
Downtown Boston
CA $1,508
per person
Oct 29 - Nov 1
found 15 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Me encantó mi estadía en The Langham. Es un excelente hotel, con una ubicación perfecta para recorrer la ciudad. La habitación muy cómoda y cuidada, especialmente la calidad de las camas y las almohadas, que hicieron que el descanso fuera excelente. Muy recomendado !!
Reviewed on Aug 25, 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
Downtown Boston
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.
Back Bay
1 out of top 10 points of interest in this area
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.
Seaport District
1 out of top 10 points of interest in this area
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.
Beacon Hill
1 out of top 10 points of interest in this area
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.
North End
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.
Cleveland Circle Hotel Deals
The Boston Hotel
40 Mt Hood Road Boston MA
Fully refundableReserve now, pay when you stay
CA $201
CA $234 total
Sep 13 - Sep 14
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $264
CA $355 total
Sep 20 - Sep 21
includes taxes & fees
9.6/10 Exceptional! (4,866 reviews)
"The hotel is very clean. Pool is not impressive. Location is great. We would definitely return."
Reviewed on Aug 26, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $178
CA $208 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (2,855 reviews)
"I chose this hotel in part because of the non cookie cutter design aesthetics. Our room was in the lofts across the street so iwe didnt feel the vibe as one would in the main part of the hotel."
Reviewed on Aug 25, 2026
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.
Frequently asked questions
How much does a Cleveland Circle vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Cleveland Circle from just CA $823. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Cleveland Circle?
Book everything in one place with our Cleveland Circle vacation packages. We have deals on hotels, flights and more that'll keep your bank account happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotels all over the world to pick from, you have countless opportunities to mix and match as you please.
How far in advance should I book my Cleveland Circle vacation?
You'll be rewarded with the biggest variety at the cheapest prices by booking your Cleveland Circle vacation early. Air carriers tend to publish flight tickets anywhere up to 12 months before departure, so start locking things in ASAP. Having said that, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Cleveland Circle travel package include?
Hotels, flights and a cool car for all your road trip adventures. Simply pick and choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on some tours and activities and watch your savings stack up. When it comes to planning your Cleveland Circle escape, you're the one in control!
What should I know before booking a Cleveland Circle travel package?
Whether it's adventure or relaxation you're craving, a Cleveland Circle 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 bigger the savings!
Can I choose my airline with a Cleveland Circle Expedia vacation package?
With a vacation package, you're the boss. Whether you're looking to fly to Cleveland Circle in business or coach, simply select from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Cleveland Circle vacation package?
Yes, you can. We get that life doesn't always go to plan, so we're here to help if you need to make changes to your Cleveland Circle vacation package. It may be possible to change or cancel your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
Stay near popular Cleveland Circle attractions
Chestnut Hill Reservation
You can take time to visit Chestnut Hill Reservation during your travels to Boston. Discover the area's art scene and cathedral.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.