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 $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 Queen Bed
    Jul 24 - Jul 26

    Hotel Ivy Boston Common + Flight

    Bay Village
    2 nights
    2.5 star property
    8.4/10 - Very good (1,457 reviews)
    "For the money, can non go wrong with this choice"
    Reviewed May 23, 2026
    Roundtrip • Buffalo (BUF) - Boston (BOS)
    BUF - BOS • Nonstop BOS - BUF • Nonstop
    CA $1,024
    CA $646
    per traveller
    found 8 hours ago
    Hotel Ivy Boston Common
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Jul 24 - Jul 28

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "This was 10/10 with everything top tier"
    Reviewed May 20, 2026
    Roundtrip • Buffalo (BUF) - Boston (BOS)
    BUF - BOS • Nonstop BOS - BUF • Nonstop
    CA $3,203
    CA $1,639
    per traveller
    found 10 hours ago
    Boston Harbor Hotel
  • Game room
    Jul 24 - Jul 26

    Meco Hotel - Hostel + Flight

    West End
    2 nights
    2.0 star property
    8.6/10 - Excellent (424 reviews)
    "good"
    Reviewed May 19, 2026
    Roundtrip • Buffalo (BUF) - Boston (BOS)
    BUF - BOS • Nonstop BOS - BUF • Nonstop
    CA $1,445
    CA $889
    per traveller
    found 9 hours ago
    Meco Hotel - Hostel
  • Lobby
    Jul 11 - Jul 18

    Nantucket Inn + Flight

    Nantucket
    7 nights
    3.5 star property
    9.2/10 - Wonderful (690 reviews)
    "The shuttle goes downtown so often and the staff is amazing"
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $6,842
    CA $4,395
    per traveller
    found 1 day ago
    Nantucket Inn
  • Lobby
    Jul 24 - Jul 28

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,242 reviews)
    "The property was very tired and not worth the price."
    Reviewed May 23, 2026
    Roundtrip • Buffalo (BUF) - Boston (BOS)
    BUF - BOS • Nonstop BOS - BUF • Nonstop
    CA $1,764
    CA $1,141
    per traveller
    found 10 hours ago
    Fairmont Copley Plaza, Boston

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

Downtown Boston

4.5/5(197 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

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $285 per night from May 29 to May 30
CA $285
CA $379 total
May 29 - May 30
includes taxes & fees
9.6/10 Exceptional! (4,365 reviews)
"It was all good."

Reviewed on May 24, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jun 7 to Jun 8
CA $227
CA $264 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (2,628 reviews)
"Everything is fantastic"

Reviewed on May 22, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from May 29 to May 30
CA $248
CA $345 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,653 reviews)
"Clean room"

Reviewed on May 23, 2026

Omni Boston Hotel at the Seaport
See all 4,120 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 . 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

Fenway Park

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

Fenway Park
Harvard University

Harvard University

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

Harvard University
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% 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.