Cleveland Circle Vacations

Book a Hotel + Flight or Car together to unlock savings

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.
  • Jul 31 - Aug 5

    Furnished Apartment Near Longwood + Flight

    North Brookline
    5 nights
    3.0 star property
    7.4/10 - 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, 2026
    Roundtrip Chicago (ORD) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    Save 100% on your flight
    $1,413
    $931
    per traveler
    found 1 day ago
    Furnished Apartment Near Longwood
  • Jul 21 - Jul 24

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,004 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Roundtrip Atlanta (ATL) - Boston (BOS)
    ATL - BOSNonstop BOS - ATLNonstop
    Save 100% on your flight
    $2,068
    $1,243
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Jul 31 - Aug 5

    The Inn at Hastings Park, Relais & Chateaux - Boston + Flight

    Lexington
    5 nights
    4.0 star property
    9.6/10 - Exceptional (256 reviews)
    "Splendid bed and breakfast"
    Reviewed April 29, 2026
    Roundtrip Chicago (ORD) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    Save 100% on your flight
    $1,694
    $1,023
    per traveler
    found 11 hours ago
    The Inn at Hastings Park, Relais & Chateaux - Boston
  • Jul 3 - Jul 10

    Iris Hotel Boston + Flight

    Coolidge Corner
    7 nights
    4.0 star property
    9.4/10 - Exceptional (557 reviews)
    "Very clean"
    Reviewed May 26, 2026
    Roundtrip Atlanta (ATL) - Boston (BOS)
    ATL - BOSNonstop BOS - ATLNonstop
    Save 100% on your flight
    $2,136
    $1,447
    per traveler
    found 1 day ago
    Iris Hotel Boston
  • Aug 4 - Aug 8

    Nantucket Inn + Flight

    Nantucket
    4 nights
    3.5 star property
    9.2/10 - Wonderful (691 reviews)
    "The shuttle goes downtown so often and the staff is amazing"
    Reviewed May 22, 2026
    Roundtrip Rockford (RFD) - Boston (BOS)
    RFD - BOS1 stop BOS - ORD1 stop
    Save 100% on your flight
    $2,592
    $1,763
    per traveler
    found 12 hours ago
    Nantucket Inn

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

Cleveland Circle Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
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

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
$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

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
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

Omni Boston Hotel at the Seaport
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

Things to do

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.