Cleveland Circle Vacation Packages

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Top Holiday Package Deals in Cleveland Circle

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,004, price is now CA $517 per person
CA $517
per person
Oct 28 - Oct 30
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,893, price is now CA $1,737 per person
CA $1,737
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Lakeside Inn

Lakeside Inn

2 out of 5
Price was CA $918, price is now CA $586 per person
CA $586
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,174 reviews)
nice stay, liked the room and bed, breakfast could have been better,

Reviewed on Aug. 23, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Price was CA $2,192, price is now CA $1,405 per person
CA $1,405
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug. 21, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,482, price is now CA $1,629 per person
CA $1,629
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Well appointed property, close to transit, downtown and highways. We had a lovely stay and look forward to returning soon.

Reviewed on Aug. 25, 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 showing a city and night scenes 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

The Boston Hotel

The Boston Hotel

2 out of 5
40 Mt Hood Road, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Sep 24 to Sep 25
CA $242
CA $282 total
Sep 24 - Sep 25
includes taxes & fees
7.2/10 Good! (696 reviews)
"."

Reviewed on Aug. 21, 2025

The Boston Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 1 to Sep 2
CA $208
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
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 $263 per night from Sep 1 to Sep 2
CA $263
CA $363 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
See all 3,702 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
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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 $517. 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 $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
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.