Dorchester Vacations from $269
Book a Hotel + Flight or Car together to unlock savings
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.
D. Hotel Suites & Spa
Save 100% on your flight
Price was $436, price is now $269 per person
$269
per person
Feb 26 - Mar 1
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.
Reviewed on Jan 6, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,628, price is now $1,027 per person
$1,027
per person
Mar 7 - Mar 13
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.
Reviewed on Oct 21, 2025
Boston Lodge and Suites
Dorchester
Save 100% on your flight
Price was $1,291, price is now $854 per person
$854
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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
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(2,415 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.
Dorchester Hotel Deals
Home2 Suites by Hilton Boston South Bay
15 JAN KARSKI WAY Boston MA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $133 total per night from Jan 21 to Jan 22
$133 total
Jan 21 - Jan 22
Total with taxes and fees
8.8/10 Excellent! (939 reviews)
I loved the rooms were so modern and spacious absolutely loved it!! The parking situation was the only thing odd and kinda not convenient. The parking area looked shady and was a bit of a walk since it's on the other side of the building next door.
Reviewed on Jan 7, 2026
Harborside Inn Of Boston
185 State St Boston MA
$119 nightly
The price is $139 total per night from Jan 19 to Jan 20
$139 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (6,144 reviews)
The staff was so nice and the check-in was easy. It was a nicely decorated boutique hotel that I would definitely stay in again. It was close to absolutely everything; the Freedom Trail, North End, Harbor, Boston Common, and there was a subway station immediately outside of the hotel. The only downside ...
Reviewed on Jan 14, 2026
Hilton Boston Back Bay
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $169 total per night from Jan 22 to Jan 23
$169 total
Jan 22 - Jan 23
Total with taxes and fees
8.4/10 Very Good! (1,241 reviews)
Check in was great. I'm tall, so I struggle with looking down at name tags. It feels awkward, especially if someone presents as female, I am a male. My check in attendant was helpful, kind, and knowledgeable. I appreciate them, but I didn't catch their name. Maybe at check there could be a nameplate? ...
Reviewed on Jan 12, 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 Dorchester
John F. Kennedy Presidential Library and Museum
4.5/5(9 reviews)
You can study the exhibits at John F. Kennedy Presidential Library and Museum, a museum with a storied past, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this walkable area.
University of Massachusetts Boston
3/5(1 review)
Enjoy the collegiate vibe when you visit University of Massachusetts Boston, during your trip to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
Edward Kennedy Institute for the US Senate
Explore the campus of Edward Kennedy Institute for the US Senate, during your travels in Boston. Stroll along the waterfront or attend a sporting event in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
92% of travellers recommend
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- Boston Vacations
- Boston Museum of Fine Arts
- Adams/King Playground
- Franklin Park Zoo
- Shirley-Eustis House
- Visit Boston
- Isabella Stewart Gardner Museum
- Massachusetts Archives and Commonwealth Museum
- Our Lady of Czestochowa Roman Catholic Church
- Samuel Adams Brewery
- John F. Kennedy Presidential Library and Museum
- Forest Hills Cemetery
- Columbus Park
- Axiom
- Boston Medical Center
- South Boston Vacations
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- Visit Marina Bay
- Museum of Science
- Visit Roxbury
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
