Cleveland Circle Vacations from $352
Book a Hotel + Flight or Car together to unlock savings
Photo by Melody Jeng
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Cleveland Circle Vacation
Cleveland Circle is calling! Whatever type of break you're planning, you can see and experience the best of this neighborhood with a Cleveland Circle vacation package. When it's time to take in the sights, you'll find a lot of big-name attractions nearby including Boston College, Agganis Arena and Paradise Rock Club. Visit one, two or more during your trip to Cleveland Circle. Don't just dream it — do it! Secure your perfect Cleveland Circle vacation with Expedia and travel your way.
The Latest Cleveland Circle Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Boston Hotel
Brighton
Save 100% on your flight
Price was $526, price is now $352 per person
$352
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.4/10 Good! (802 reviews)
Otel gerçekten çok temizdi, fiyatı da oldukça uygundu. Daha önce kaldığım otellere göre hem temizlik açısından çok iyiydi hem de sonunda düzgün bir kahvaltı bulabildim. 👍”
Reviewed on Nov 28, 2025
Iris Hotel Boston
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant.
I would stay there anytime I'm in Brookline
Reviewed on Nov 22, 2025
Premier Suites - Bay Village
Bay Village
Save 100% on your flight
Price was $743, price is now $461 per person
$461
per person
Feb 3 - Feb 10
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
6.2/10 (245 reviews)
Great central location, but very over priced for what you get. Felt like I was going to fall through the floor. Super old building and nothing works that well.
Internet on tv didn't work. Bath plug/stopper didn't work.
Electric hotplate didn't work.
Don't bring a large suitcase as the stairs are very narrow and steep and I had to lug it up to the 4th floor.
Reviewed on Nov 10, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $971, price is now $644 per person
$644
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything about this hotel is exceptional.
Reviewed on Nov 29, 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
4.5/5(2,415 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.
Cleveland Circle Hotel Deals
The Boston Hotel
40 Mt Hood Road Boston MA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $85 total per night from Dec 9 to Dec 10
$85 total
Dec 9 - Dec 10
Total with taxes and fees
7.4/10 Good! (814 reviews)
Good
Reviewed on Nov 26, 2025
Seaport Hotel Boston
1 Seaport Lane Boston MA
$143 nightly
The price is $166 total per night from Nov 30 to Dec 1
$166 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (3,738 reviews)
The food is very good. I have simple tastes and appreciated that the food was not over-processed but was simple yet extremely flavorful.
Reviewed on Nov 25, 2025
citizenM Boston North Station
70 Causeway Street Boston MA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $130 total per night from Dec 15 to Dec 16
$130 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (4,107 reviews)
Rooms were clean, staff was friendly
Reviewed on Nov 25, 2025
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.
Discover the most popular places to visit in Cleveland Circle
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Boston Common
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.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
90% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
$35
per adult
100% of travellers recommend
Explore a world of travel with Expedia
- Boston Hotels
- Hotels near Fenway Park
- Hotels near Boston College
- Hotels near Cleveland Circle Station
- Hotels near Downtown Boston
- Hotels near Reservoir Station
- Hotels near Chestnut Hill Av. Station
- Hotels near Commonwealth
- Hotels near Chestnut Hill Reservoir
- Cheap Hotels in Boston
- Hotels near Sutherland Rd. Station
- Town Houses in Sutherland Rd. Station
- Hotels near South St. Station
- Hotels near Dean Rd. Station
- Hotels near Beaconsfield Station
- Hotels near Washington St. Station
- Hotels near Brighton
- Hotels near St. Elizabeth's Medical Center
- Hotels near Aspinwall Hill
- Cheap Hotels in Brighton
- Hotels near Boston College Station
- Hotels near Alumni Stadium
- B&B in Boston College Station
- Hotels near Corey Hill
- Hotels near Logan Intl.
- Hotels near Warren St. Station
- Hotels near Chestnut Hill Station
- B&B in Chestnut Hill Station
- Brookline Hotels
- Houseboats in Fairbanks St. Station
- Apartments in Allston St. Station
- B&B in Allston St. Station
- Hotels near Allston St. Station
- Cambridge Hotels
- Hotels near McMullen Museum
- Hotels near Brandon Hall Station
- Hotels near Griggs Park
- Hotels near Griggs St. Station
- Hotels near Woodland Heath
- Hotels near Frederick Law Olmsted National Historic Site
- Chestnut Hill Hotels
- Hotels near Brookline Hills Station
- Hotels near GASP
- Hotels near Oak Square
- Hotels near Harvard Av. Station
- Hotels near Great Scott
- Hotels near Brookline Farmers Market
- Luxury Hotels in Chestnut Hill
- B&B in Chestnut Hill
- Marriott Hotels & Resorts in Chestnut Hill
- 5 Star Hotels in Chestnut Hill
- Extended Stay America Hotels in Chestnut Hill
- Motels in Chestnut Hill
- Hostels in Chestnut Hill
- 4 Star Hotels in Chestnut Hill
- Resorts in Chestnut Hill
- Guest Houses in Chestnut Hill
- Hotels near Brighton Music Hall
- Hotels near Allston
- Cheap Hotels in Brookline
- Hotels near Coolidge Corner Theatre
- Cheap Hotels in Allston
- Hotels near Koreatown
- Hotels near Packard's Corner
- B&B in Brookline
- Boutique Hotels in Brookline
- Boston Vacations
- Boston Museum of Fine Arts
- St. Elizabeth's Medical Center
- Alumni Stadium
- Boston College
- Frederick Law Olmsted National Historic Site
- Great Scott
- Brookline Farmers Market
- Chestnut Hill Vacations
- Brighton Music Hall
- Isabella Stewart Gardner Museum
- Coolidge Corner Theatre
- Brookline Vacations
- Visit Chestnut Hill
- Paradise Rock Club
- Agganis Arena
- Car rentals near Boston
- Car rental Boston Airport (BOS)
- Car rentals near Chestnut Hill Reservoir
- Car rentals near St. Elizabeth's Medical Center
- Car rentals near Brighton
- Car rentals near Boston College
- Car rentals near Brookline
- Car rentals near Chestnut Hill
- Hertz Rental Cars in Chestnut Hill
- Enterprise Rental Cars in Chestnut Hill
- Enterprise Rental Cars in Brookline
- Car rentals near Coolidge Corner Theatre
- Hertz Rental Cars in Brookline
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.