Cleveland Circle Vacation Packages
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- By the Sea Guests Bed & Breakfast & Suites
Jul 31 - Aug 3By the Sea Guests Bed & Breakfast & Suites + Flight
Dennis Port3 nights9.2/10 - Wonderful (187 reviews)"Such a cute place to stay and the staff are so helpful and welcoming!!"Reviewed May 31, 2026Roundtrip • Toronto (YTZ) - Boston (BOS)YTZ - BOS • Nonstop BOS - YYZ • NonstopCA $1,449CA $929found 4 hours agoper traveller - Boston Harbor Hotel
Jul 31 - Aug 4Boston Harbor Hotel + Flight
North End4 nights9.8/10 - Exceptional (1,000 reviews)"Wonderful classic harbor front hotel. Very nice front desk. Would stay again"Reviewed May 25, 2026Roundtrip • Toronto (YTZ) - Boston (BOS)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $3,038CA $1,554found 1 day agoper traveller - Hotel Ivy Boston Common
Jul 31 - Aug 4Hotel Ivy Boston Common + Flight
Bay Village4 nights8.4/10 - Very good (1,470 reviews)"Staff were mostly nice, but overall one of the worst hotels I’ve ever stayed in. WiFi didn’t work for 3 days straight, the initial room I was in had blacked out windows, housekeeping doesn’t clean the rooms, the rooms are smaller than a jail cell, there is a 2 inch gap at the bottom of every door. It’s incredibly loud, the lift can be heard throughout the whole hotel every time someone uses it. If you have any other options, do not book this hotel"Reviewed May 30, 2026Roundtrip • Toronto (YTZ) - Boston (BOS)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $1,686CA $993found 1 day agoper traveller - Fairmont Copley Plaza, Boston
Aug 14 - Aug 22Fairmont Copley Plaza, Boston + Flight
Back Bay8 nights9.0/10 - Wonderful (1,243 reviews)"I recently stayed at the Fairmont Boston and unfortunately the property felt very outdated and not well maintained compared to what I expected from a Fairmont hotel. While the location is convenient and the staff were generally polite, the overall condition of the hotel needs significant updates. The rooms showed noticeable wear and tear, including older furniture, dated décor, and areas that did not feel particularly clean or refreshed. The hallways and common areas also felt tired and lacked..."Reviewed May 29, 2026Roundtrip • Toronto (YYZ) - Boston (BOS)YYZ - BOS • Nonstop BOS - YYZ • NonstopCA $3,209CA $1,986found 1 day agoper traveller - The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Jul 21 - Jul 28The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat + Flight
East Wareham7 nights10/10 - Exceptional (9 reviews)"I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler "Reviewed October 8, 2025Roundtrip • Toronto (YYZ) - Boston (BOS)YYZ - BOS • Nonstop BOS - YYZ • NonstopCA $8,949CA $5,652found 1 day agoper traveller
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(197 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
The price is CA $354 per night from Jun 28 to Jun 29
CA $354
CA $460 total
Jun 28 - Jun 29
includes taxes & fees
9.6/10 Exceptional! (4,390 reviews)
"Clean room and the best hotel staff I have come across friendly and accommodating for little ones. Out little guy played "work" with a worker because she looked lonely by herself hm. From valet to the restaurant, all the employees are too of the line."
Reviewed on May 30, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jun 7 to Jun 8
CA $189
CA $220 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (2,635 reviews)
"Loved it so much I came back for a second stay"
Reviewed on May 30, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
The price is CA $308 per night from Jun 7 to Jun 8
CA $308
CA $415 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (4,659 reviews)
"The room was a little small and condensed without a separate bathroom area, but it was spectacular and the food amenities staff view were fantastic. Highly recommend and worth the price."
Reviewed on May 30, 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.
Frequently asked questions
Discover the most popular places to visit in Cleveland Circle
Fenway Park
4.5/5(310 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
4.5/5(28 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(284 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 Old Town Trolley Hop-on Hop-Off City Tour
CA $79
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $115
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.