Downtown Crossing Vacations from $531
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Your Downtown Crossing Vacation
Take all the hassle out of organizing your next escape with a Downtown Crossing vacation package. Immerse yourself in the sounds and sights of this wonderful neighborhood and enjoy what it has to offer. When it's time to get out and explore, you'll find loads of awesome attractions nearby including Fenway Park, Boston Common and Faneuil Hall Marketplace. Tick off one or all during your trip to Downtown Crossing. No matter what your ideal Downtown Crossing vacation looks like, you can turn it into reality with Expedia.
The Latest Downtown Crossing Vacation Packages
Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $861, price is now $531 per person
$531
per person
Aug 28 - Aug 31
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year
Reviewed on Jun 18, 2026
Boston Harbor Hotel
North End
Price was $2,473, price is now $1,174 per person
$1,174
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026
Good Hotels Boston
South End
Save 100% on your flight
Price was $1,051, price is now $623 per person
$623
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.
Reviewed on May 23, 2026
Beachside Village Resort
Save 100% on your flight
Price was $1,019, price is now $632 per person
$632
per person
Aug 28 - Aug 31
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (111 reviews)
This property was extraordinary. My late check-in was seamless, and my room was spacious and extremely comfortable. The staff (my apologies, I forgot the front desk staff's names) were friendly, helpful, and professional. I had one minor maintenance issue that Joe resolved promptly and courteously. My room was directly across from the water, so I had a great view from my room and balcony. Having a kitchen made me feel right at home. My local friends, etc., were extremely impressed by the property layout, location, and price. Downtown was within walking distance (about a mile), and the beach was nearby. I will definitely plan a return visit here, but it would be hard to top my last stay.
Reviewed on Jun 5, 2026
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Save 100% on your flight
Price was $1,170, price is now $726 per person
$726
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (3,158 reviews)
Staff were great, friendly and helpful
Reviewed on Jun 21, 2026
Where to stay in Downtown Crossing
Find the best Downtown Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Crossing
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.
Downtown Crossing Hotel Deals
The Godfrey Hotel Boston
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $344 total per night from Jul 19 to Jul 20
$344 total
Jul 19 - Jul 20
Total with taxes and fees
9.4/10 Exceptional! (5,118 reviews)
"Hidden Gem.. I wouldn’t hesitate to stay here sgain"
Reviewed on Jun 22, 2026
Omni Parker House
60 School St Boston MA
Fully refundableReserve now, pay when you stay
$304 nightly
The price is $354 total per night from Jul 5 to Jul 6
$354 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (3,575 reviews)
"Room was adequately sized for a short stay and was serviced very well each day. The bars were very good however not open all day. Drinks prices were comparable with local bars. Didn’t use the restaurant. The staff were all very helpful and friendly. Overall a very good 4 star hotel in an excellent ..."
Reviewed on Jun 22, 2026
Hyatt Regency Boston
One Avenue De Lafayette Boston MA
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $230 total per night from Jul 5 to Jul 6
$230 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (2,100 reviews)
"The room was extremely clean. When arrival, the staff was friendly, professional and warm. The next day, we ordered breakfast and the food was amazing and most of all, presentable!"
Reviewed on Jun 21, 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 Downtown Crossing
Granary Burying Ground
Samuel Adams and Paul Revere have their final resting places in the heart of the city they defended, within a stately 17th-century cemetery.
Old South Meeting House
Visit this important colonial-America site that witnessed much of the lead-up to the American Revolution and has long played a part in Boston history.
Orpheum Theater
Enjoy a show at Orpheum Theater, a storied theater in Boston. Discover the fascinating museums and notable monuments in this vibrant area.
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.