Jamaica Plain Vacations from $269
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Your Jamaica Plain Vacation
Book a Jamaica Plain vacation package and immerse yourself in the rhythm and vibe of this captivating neighborhood. With all your travel plans worked out, the only thing you need to focus on here is having an absolute ball. Kick off your trip to Jamaica Plain with a visit to nearby attractions such as Fenway Park, Copley Place and Boston Museum of Fine Arts. Whatever your travel goals or the size of your budget, booking your perfect Jamaica Plain vacation is simple with Expedia.
The Latest Jamaica Plain 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 24 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
Boston Lodge and Suites
Dorchester
Price was $625, price is now $275 per person
$275
per person
Feb 27 - Mar 1
found 5 hours ago
Roundtrip flight included
Miami (MIA) 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
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 17 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
Fairmont Copley Plaza, Boston
Back Bay
Price was $1,420, price is now $995 per person
$995
per person
Mar 29 - Apr 3
found 6 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Location was perfect, staff was wonderful and the foyer and lobby and the bar/ restaurant was amazing! The guest rooms were good, bed was comfortable and room was immaculate! My only complaint would be the water pressure in the shower was weak! Other than that a very good experience!
Reviewed on Jan 13, 2026
Where to stay in Jamaica Plain
Find the best Jamaica Plain areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica Plain
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.
Jamaica Plain Hotel Deals
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
The Langham, Boston
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
$395 nightly
The price is $460 total per night from Jan 18 to Jan 19
$460 total
Jan 18 - Jan 19
Total with taxes and fees
9.6/10 Exceptional! (1,001 reviews)
Amazing service and staff
Reviewed on Jan 15, 2026
Encore Boston Harbor
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $242 total per night from Feb 17 to Feb 18
$242 total
Feb 17 - Feb 18
Total with taxes and fees
9.6/10 Exceptional! (3,511 reviews)
It was a great experience
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 Jamaica Plain
Arnold Arboretum
Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.
Axiom
You can study the exhibits at Axiom, a museum with a story of its own, during your travels to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
92% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
$35
per adult
100% of travellers recommend
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- Boston Vacations
- Boston Museum of Fine Arts
- Axiom
- Samuel Adams Brewery
- Isabella Stewart Gardner Museum
- Arnold Arboretum
- Forest Hills Cemetery
- Larz Anderson Auto Museum
- Frederick Law Olmsted National Historic Site
- Franklin Park Zoo
- Brookline Vacations
- Brigham and Women's Hospital
- Warren Anatomical Museum
- Visit Roxbury
- Dana-Farber Cancer Institute
- Children's Hospital Boston
- Visit Brookline
- Car rentals near Boston
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.