Cleveland Circle Vacations from $343
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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 Wylie Inn and Conference Center at Endicott College
Save 100% on your flight
Price was $490, price is now $343 per person
$343
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (1,160 reviews)
Courteous staff, great work out room, nice rooms!
Reviewed on Mar 1, 2026
AutoCamp Cape Cod
Save 100% on your flight
Price was $857, price is now $577 per person
$577
per person
May 19 - May 24
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.4/10 Exceptional! (305 reviews)
We had a wonderful stay here on Valentine’s Day weekend. It was the first time we stayed at a camp ground and definitely the first time staying in an AirStream. The clubhouse was sooo nice! Staff were great. Good menu options and merch as well. Picked up an AutoCamp beanie! Live music was awesome. My only complaint is we had no hot water! That was tough being that we are in the middle of the winter and it was already freezing outside. Hot showers would have been nice! Other than that we’re planning for a summer weekend here
Reviewed on Feb 17, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,287, price is now $871 per person
$871
per person
Apr 3 - Apr 7
found 23 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.
Reviewed on Oct 21, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,055, price is now $726 per person
$726
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on Jan 25, 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
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
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $182 total per night from Mar 8 to Mar 9
$182 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (4,025 reviews)
Staff were exceptionally helpful and pleasant. Loved our stay
Reviewed on Mar 2, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Mar 8 to Mar 9
$214 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (4,485 reviews)
Staff very friendly , room very clean Very comfortable all Thanks for all
Reviewed on Mar 2, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $183 total per night from Mar 22 to Mar 23
$183 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (3,116 reviews)
Yes
Reviewed on Mar 3, 2026
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.
Gillette Stadium
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.
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.
Things to do
Harvard University Campus Guided Walking Tour
$23
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
92% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
$45
per adult
100% 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.