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 $1,096 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

Top Holiday Package Deals in Cleveland Circle

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,847, price is now CA $1,207 per person
CA $1,207
per person
May 22 - May 25
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints.

Reviewed on Mar 14, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,953, price is now CA $1,748 per person
CA $1,748
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,449, price is now CA $1,561 per person
CA $1,561
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $4,356, price is now CA $2,854 per person
CA $2,854
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (526 reviews)
Fantastic location, close to Mass Gen. Restaurant on property was also very good.

Reviewed on Mar 19, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,408, price is now CA $2,356 per person
CA $2,356
per person
May 27 - May 30
found 8 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
I went to raffles Boston for fiancés birthday and I called a week ahead to get the room decorated for her special day and when I showed up the room was not decorated, I then called and said they didn’t decorate the room like I asked so they asked if they could come up during dinner and decorate so I agreed. When we returned from dinner the room was “decorated”, the sign was hanging off the ceiling and decorations taped poorly and just looked awful. Very disappointed considering this is a expensive 5 start hotel

Reviewed on Mar 12, 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 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

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 $186 per night from Apr 5 to Apr 6
CA $186
CA $272 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (4,520 reviews)
Clean room, great location and staff

Reviewed on Mar 20, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Apr 5 to Apr 6
CA $201
CA $290 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (3,119 reviews)
Highly recommend

Reviewed on Mar 19, 2026

Hilton Boston Park Plaza
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is CA $158 per night from Apr 5 to Apr 6
CA $158
CA $230 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (4,067 reviews)
The staff was so nice and friendly! Great hotel!

Reviewed on Mar 19, 2026

Seaport Hotel Boston
See all 4,109 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 $1,207. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.