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

Top Holiday Package Deals in Cleveland Circle

Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,254, price is now CA $761 per person
CA $761
per person
Aug 20 - Aug 23
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Great hotel staff, great location, great room :)

Reviewed on Jul 8, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,956, price is now CA $1,320 per person
CA $1,320
per person
Aug 21 - Aug 25
found 12 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Staff was super friendly and accommodating, and we very much enjoyed our stay. Room was good, location is great right on the edge of town and easily accessible.

Reviewed on Jul 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,502, price is now CA $2,440 per person
CA $2,440
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,772, price is now CA $1,957 per person
CA $1,957
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,301, price is now CA $933 per person
CA $933
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Aug 9 to Aug 10
CA $214
CA $291 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,431 reviews)
"Poor bar closed early nowhere to get breakfast early"

Reviewed on Jul 8, 2026

Hyatt Regency Boston/Cambridge
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 $268 per night from Jul 26 to Jul 27
CA $268
CA $360 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,541 reviews)
"The Seaport Hotel was great. Lots of fun events nearby and the hotel was clean, with a great staff"

Reviewed on Jul 8, 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 $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,726 reviews)
"Great hotel. Loved the vibe and room was great!"

Reviewed on Jul 8, 2026

The Revolution Hotel
See all 4,094 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 $761. 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.
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
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 $116
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.