Jamaica Plain Vacations from $481
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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.
Boston Lodge and Suites
Dorchester
Price was $1,473, price is now $481 per person
$481
per person
Jan 6 - Jan 11
found 2 days ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Price was $1,430, price is now $1,014 per person
$1,014
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
10/10 Exceptional! (11 reviews)
We had a great experience staying in the crab house. The cottage was well maintained and had everything we needed to enjoy our stay. The staff was friendly, helpful, and genuinely care. Ken was fantastic, you can really tell he cares about ensuring guests have a great experience. 10/10 experience, would recommend this spot to anyone looking for a great stay on the cape.
Reviewed on Jul 27, 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
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
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $193 total per night from Nov 23 to Nov 24
$193 total
Nov 23 - Nov 24
Total with taxes and fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $117 total per night from Nov 23 to Nov 24
$117 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (3,028 reviews)
"Good stay for the three nights"
Reviewed on Nov 11, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $152 total per night from Nov 23 to Nov 24
$152 total
Nov 23 - Nov 24
Total with taxes and fees
9.6/10 Exceptional! (5,210 reviews)
"2nd time staying at Seaport Hotel in a month. It's definitely becoming my regular spot in Boston."
Reviewed on Nov 11, 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 Jamaica Plain attractions
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Harbor Sightseeing Cruise
$51
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
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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.