Cleveland Circle Vacations
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Photo by Melody Jeng
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.
Price found within the past 48 hours. Click for updated prices.
- Furnished Apartment Near Longwood
Jul 31 - Aug 5Furnished Apartment Near Longwood + Flight
North Brookline5 nights7.4/10 - Good (3 reviews)"The owners of this property canceled on me the night before my trip, blaming it on a “maintenance issue”. They originally reassigned me to a different unit but then canceled it in full. It was difficult to contact the property and I did not even receive a full refund. Would not recommend staying at this place, a would not recommend this ownership group that works through Evonify Stays."Reviewed April 7, 2026Roundtrip • Chicago (ORD) - Boston (BOS)ORD - BOS • Nonstop BOS - ORD • Nonstop - Boston Harbor Hotel
Jul 21 - Jul 24Boston Harbor Hotel + Flight
North End3 nights9.8/10 - Exceptional (1,004 reviews)"Wonderful classic harbor front hotel. Very nice front desk. Would stay again"Reviewed May 25, 2026Roundtrip • Atlanta (ATL) - Boston (BOS)ATL - BOS • Nonstop BOS - ATL • Nonstop - The Inn at Hastings Park, Relais & Chateaux - Boston
Jul 31 - Aug 5The Inn at Hastings Park, Relais & Chateaux - Boston + Flight
Lexington5 nights9.6/10 - Exceptional (256 reviews)"Splendid bed and breakfast"Reviewed April 29, 2026Roundtrip • Chicago (ORD) - Boston (BOS)ORD - BOS • Nonstop BOS - ORD • Nonstop - Iris Hotel Boston
Jul 3 - Jul 10Iris Hotel Boston + Flight
Coolidge Corner7 nights9.4/10 - Exceptional (557 reviews)"Very clean"Reviewed May 26, 2026Roundtrip • Atlanta (ATL) - Boston (BOS)ATL - BOS • Nonstop BOS - ATL • Nonstop - Nantucket Inn
Aug 4 - Aug 8Nantucket Inn + Flight
Nantucket4 nights9.2/10 - Wonderful (691 reviews)"The shuttle goes downtown so often and the staff is amazing"Reviewed May 22, 2026Roundtrip • Rockford (RFD) - Boston (BOS)RFD - BOS • 1 stop BOS - ORD • 1 stop
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(2,438 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
$236 nightly
The price is $274 total per night from May 29 to May 30
$274 total
May 29 - May 30
Total with taxes and fees
9.6/10 Exceptional! (4,373 reviews)
"Great location for seeing the Freedom Trail sites of Boston. Wonderful views overlooking the harbor."
Reviewed on May 26, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $209 total per night from Jun 7 to Jun 8
$209 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (2,634 reviews)
"Great location great price. Cozy an quirky. The bathroom down the hall was no trouble. Clean and with privacy."
Reviewed on May 26, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $249 total per night from May 29 to May 30
$249 total
May 29 - May 30
Total with taxes and fees
9.2/10 Wonderful! (4,660 reviews)
"Beautiful clean room"
Reviewed on May 26, 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
4.5/5(2,543 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
4.5/5(400 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.
Harvard University
4.5/5(1,983 reviews)
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
$84
per adult
92% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
$45
per adult
98% of travellers recommend
Harvard University Campus Guided Walking Tour
$23
per adult
92% 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
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- Luxury Hotels in Chestnut Hill
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- 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.