Cleveland Circle Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Cleveland Circle

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Boston Logan Airport - Revere by IHG

Staybridge Suites Boston Logan Airport - Revere by IHG

3 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (536 reviews)
Staff were amazing! Room was great, didn’t care for the tv placement but other than that it was clean and quiet and plenty of places near to eat and shop. Also love the free shuttle to and from the airport!

Reviewed on Jul. 9, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 12 - Aug 16
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Great hotel, friendly staff, great gym and spa.

Reviewed on Jul. 7, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 12 - Aug 16
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
First class hotel with incredible staff and food onsite. Walk to anywhere downtown and the north end for great Italian food

Reviewed on Jul. 8, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,026 reviews)
Place was beautiful well kept and very clean

Reviewed on Jul. 8, 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
Downtown Boston which includes night scenes and a city as well as a small group of people

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 hotels in Downtown Boston

Cleveland Circle Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $392 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,651 reviews)
"We just had a wonderful stay at the Omni seaport ! It was July 4th weekend so it was. Busy but still the hotel was very attentive and organized . From valet to front desk , to the pool staff everyone was friendly and helpful and also had in room dining for breakfast from kestra ans it was amazing ..."

Reviewed on Jul. 8, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jul 13 to Jul 14
CA $252
CA $293 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,394 reviews)
"Check in was self serving and simple. Big fan of the room controls through the app and iPad in the room. Blackout curtains and complementary refillable water bottles are a fantastic incentive."

Reviewed on Jul. 8, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 13 to Jul 14
CA $282
CA $328 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (5,289 reviews)
"The room was very roomy for a Boston Hotel! Beds were comfortable and the service was excellent. We loved the location and convenience to all areas of Boston. We will stay here again!"

Reviewed on Jul. 8, 2025

Harborside Inn Of Boston
See all 3,686 properties in Cleveland Circle
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $685. 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.

Discover the most popular places to visit in Cleveland Circle

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

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.

Boston Common

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.