Dorchester Vacations from $706
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Your Dorchester Vacation
Packed with charm and personality, Dorchester offers everything from nature to dining. Experience the wonders of this neighborhood the easy way with a personalized Dorchester vacation package. When it's time to explore the sights, you'll find loads of big-name attractions nearby including Boston Museum of Fine Arts, Northeastern University and John F. Kennedy Presidential Library and Museum. Tick off one, two or all during your trip to Dorchester. Don't just think about it — make it happen! Book your ideal Dorchester vacation with Expedia and experience travel your way.
The Latest Dorchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,122, price is now $706 per person
$706
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
A beautiful Hotel w an excellent staff that provides superior service and helps to make our stay memorable. We will be back again.
Reviewed on Jul 6, 2026
Nantucket Inn
Save 100% on your flight
Price was $2,563, price is now $1,566 per person
$1,566
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
Great property. The best pillows we have had in a long time. Convenient shuttle service and loved the free bikes!
Reviewed on Jul 7, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
Price was $5,471, price is now $3,391 per person
$3,391
per person
Aug 12 - Aug 17
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 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 on Oct 8, 2025
Boston Lodge and Suites
Dorchester
Save 100% on your flight
Price was $1,450, price is now $899 per person
$899
per person
Sep 24 - Sep 28
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Good Hotels Boston
South End
Save 100% on your flight
Price was $1,588, price is now $1,039 per person
$1,039
per person
Sep 24 - Sep 28
found 24 hours 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
Where to stay in Dorchester
Find the best Dorchester areas and neighborhoods for the activities you enjoy most. Learn more about Dorchester
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.
Dorchester Hotel Deals
Ramada by Wyndham Boston
800 Morrissey Blvd Boston MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Aug 2 to Aug 3
$124 total
Aug 2 - Aug 3
Total with taxes and fees
6.8/10 (1,775 reviews)
"Some staff was very helpful, some not at all, no ice machine, fridge does not get cold, tv only had antenna channels. Breakfast was good, ro clean but ceiling falling apart in one area leaving debris on the floor. Elevator was scary. Only one luggage carriage and staff insisted house keeping needed ..."
Reviewed on Jul 7, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
$168 nightly
The price is $195 total per night from Jul 26 to Jul 27
$195 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (2,424 reviews)
"The staff were fantastic at all times. We went there to see the fireworks and gave up, my husband can only walk for so long because of health issues, we had dinner at the hotel and the service was horrible, we waited for an overcooked dried out hamburger for over an hour, first they bused in two ..."
Reviewed on Jul 7, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
$219 nightly
The price is $254 total per night from Jul 26 to Jul 27
$254 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (4,535 reviews)
"Great location. Friendly staff. Clean and accessible. Tamo Bar/Lounge was very good. Would stay again."
Reviewed on Jul 7, 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.
Stay near popular Dorchester attractions
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
City Cruises Boston: Historic Sightseeing Cruise
$46
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Cathedral of the Holy Cross
- Northeastern University
- New England Conservatory of Music
- Massachusetts State House
- Forest Hills Cemetery
- Granary Burying Ground
- Theatre District Vacations
- Boston Massacre Site
- Castle Island
- New England Holocaust Memorial
- Charles River Esplanade
- Zakim Bunker Hill Bridge
- Christian Science Plaza
- Institute of Contemporary Art
- Hammond Castle
- Rose Fitzgerald Kennedy Greenway
- The Freedom Trail
- Boston Medical Center
- Franklin Park Zoo
- Memorial Hall
- Larz Anderson Auto Museum
- Mcphs University - Boston
- Isabella Stewart Gardner Museum
- Massachusetts Archives and Commonwealth Museum
- Harpoon Brewery
- Boston City Hall Plaza
- Boston Public Garden
- Newbury Street
- Thompson Island
- Bunker Hill Monument
- Charles Playhouse
- Museum of Science
- Our Lady of Czestochowa Roman Catholic Church
- South Boston Vacations
- Old Corner Bookstore
- Harvard Museum of Natural History
- Old South Meeting House
- Longfellow Bridge
- Berklee College of Music
- Quincy Market
- Flynn Cruiseport Boston
- Beth Israel Deaconess Medical Center
- Faneuil Hall Marketplace
- Granite Links Golf Club
- Axiom
- Louisburg Square
- Trinity Church Boston
- Boston Public Library
- Faneuil Hall Visitor Center
- Prudential Tower
- Salem Vacations
- Old North Church
- Downtown Boston Vacations
- Copley Square
- Longwood Medical Area
- Seaport World Trade Center
- Commonwealth Avenue Mall
- Copp's Hill Burying Ground
- Massachusetts Institute of Technology
- George Washington Statue
- Brigham and Women's Hospital
- Wollaston Beach
- Boston Common
- Harvard University
- Boston Marathon
- Stata Center
- Copley Place
- Paul Revere House
- Brookline Vacations
- Boston Museum of Fine Arts
- Samuel Adams Brewery
- Warren Anatomical Museum
- Church of the Covenant
- Joslin Diabetes Center
- Revere Beach
- Fenway Park
- Dana-Farber Cancer Institute
- Park Street Church
- Boston Symphony Hall
- Boston Children's Museum
- Boston Tea Party Ship
- Hynes Convention Center
- Shirley-Eustis House
- The Fens
- Old State House
- Fenway–Kenmore Vacations
- New England Conservatory Jordan Hall
- Boston Vacations
- Boston Marathon Finish Line
- Kendall Square
- Td Garden
- New England Aquarium
- The Shops at Prudential Center
- Statue of Paul Revere
- Boston Convention and Exhibition Center
- Old South Church
- Massachusetts General Hospital
- Mount Auburn Cemetery
- Harborwalk
- Jamaica Plain Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.