Cleveland Circle Vacations from $429
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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 Coonamessett
Price was $611, price is now $429 per person
$429
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.8/10 Excellent! (709 reviews)
The Coonamessett is a beautiful inn overlooking the water. The suite I stayed in was absolutely stunning. Breakfast is excellent with some vegan options such as mixed fruit and oat milk.
The inn is extremely comfortable, clean, and well-maintained. My suite even had two walk-in closets.
Reviewed on Nov 11, 2026
Boston Lodge and Suites
Dorchester
Price was $1,218, price is now $452 per person
$452
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Price was $1,521, price is now $1,055 per person
$1,055
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
10/10 Exceptional! (11 reviews)
We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape.
Reviewed on Jul 27, 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
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 Rd Boston MA
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $63 total per night from Dec 1 to Dec 2
$63 total
Dec 1 - Dec 2
Total with taxes and fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $193 total per night from Nov 22 to Nov 23
$193 total
Nov 22 - Nov 23
Total with taxes and fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $113 total per night from Dec 14 to Dec 15
$113 total
Dec 14 - Dec 15
Total with taxes and fees
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.
Stay near popular Cleveland Circle attractions
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Harbor Sightseeing Cruise
$51
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.