Downtown Crossing Vacations from $295

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $461, price is now $295 per person
$295
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,111 reviews)
Spotlessroom. Nice temperature

Reviewed on Nov 28, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $823, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant. I would stay there anytime I'm in Brookline

Reviewed on Nov 22, 2025

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

3 out of 5
Spring Hill
Save 100% on your flight
Price was $559, price is now $346 per person
$346
per person
Jan 1 - Jan 6
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
The room was relatively spacious and super chic. The lobby and adjacent restaurant were such well designed (aesthetically pleasing!) spaces too. Great experience.

Reviewed on Nov 21, 2025

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Save 100% on your flight
Price was $636, price is now $407 per person
$407
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.8/10 Excellent! (1,000 reviews)
The staff were friendly, the location was conveniently located making it easy to walk around the city and overall the rooms were very clean and comfortable. We enjoyed the bedding and aesthetic of the rooms. The hotel is in a very old building and there were a few things that could have been fixed. The water knob was loose and kept falling during a shower, leaving us showering with extremely hot water. There was a hole in the wall where the electrical box was (the cover was taken off and never replaced). The walls are extremely thin. After 10pm you could hear every little thing the neighbours were saying and 2 of our 4 nights were could barely sleep due to the sounds of music, tv, and screaming from adjacent rooms. For the price we paid we would have expected a higher quality room, especially since there is a “resort fee” cost for basic things like water and wifi that we would have rather opt out of.

Reviewed on Nov 25, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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 which includes night scenes and a city as well as a small group of people

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.

Find hotels in Downtown Boston

Downtown Crossing Hotel Deals

Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $242 total per night from Dec 14 to Dec 15
$242 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (3,210 reviews)
Friendly helpful staff

Reviewed on Nov 25, 2025

Omni Parker House
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $161 total per night from Dec 22 to Dec 23
$161 total
Dec 22 - Dec 23
Total with taxes and fees
9.4/10 Exceptional! (4,715 reviews)
Nice room, lovely staff and excellent location

Reviewed on Nov 24, 2025

The Godfrey Hotel Boston
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St Boston MA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $160 total per night from Nov 30 to Dec 1
$160 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (2,911 reviews)
This particular room was very small but fine for a quick 2 day trip. In a good location downtown close to all transit, coffee shops, restaurants. Lovely and helpful staff.

Reviewed on Nov 24, 2025

Club Quarters Hotel Faneuil Hall, Boston
See all 3,941 properties in Downtown Crossing
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Downtown Crossing

Old South Meeting House featuring a city, street scenes and heritage architecture

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.

Old South Meeting House
Benjamin Franklin Statue showing a statue or sculpture

Benjamin Franklin Statue

Pay homage to a notable New Englander from the 18th century, between King’s Chapel and a historic bookstore, along Boston’s Freedom Trail.

Benjamin Franklin Statue
Granary Burying Ground

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.

Granary Burying Ground

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

$35
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.