Jamaica Plain Vacations from $482
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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.
Hotel 1620 Plymouth Harbor
Plymouth Downtown Waterfront District
Price was $668, price is now $482 per person
$482
per person
May 22 - May 25
found 12 hours ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
8.2/10 Very Good! (1,005 reviews)
We did not use the pool however, it looked very nice and lots of guests were enjoying it. Yes the Air temp in our room was great. Our room was newly renovated and very nice. We will be back!
Reviewed on Mar 31, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $4,212, price is now $2,802 per person
$2,802
per person
May 10 - May 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.
Reviewed on Mar 23, 2026
Beachside Village Resort
Price was $1,918, price is now $1,362 per person
$1,362
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!
Reviewed on Nov 10, 2025
Centerboard
Nantucket Town
Save 100% on your flight
Price was $3,519, price is now $2,547 per person
$2,547
per person
Jun 13 - Jun 19
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (105 reviews)
There was hair on our bed, I ask for late due to getting dress for my wedding and I was told
Reviewed on Mar 20, 2026
Sea Crest Beach Resort
Price was $692, price is now $504 per person
$504
per person
May 22 - May 25
found 12 hours ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
8/10 Very Good! (253 reviews)
The staff were really nice and the food was good. They have an excellent location right on the beach.
Reviewed on Mar 12, 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(2,438 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.
Jamaica Plain Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $220 total per night from Apr 5 to Apr 6
$220 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (4,549 reviews)
Very nice
Reviewed on Mar 28, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $182 total per night from Apr 5 to Apr 6
$182 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (4,114 reviews)
All around good
Reviewed on Mar 30, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $231 total per night from Apr 10 to Apr 11
$231 total
Apr 10 - Apr 11
Total with taxes and fees
8.4/10 Very Good! (3,132 reviews)
Staff, room and amenities were great. Walls were so thin I heard the entire conversations in the room next to mine (they weren’t yelling). It was an adjoining room so request not to be in one of those and it should be fine. Otherwise hotel was great.
Reviewed on Mar 30, 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
$84
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$56
per adult
92% of travellers recommend
City Cruises Boston: Premier Elegant Dinner Cruise
$146
per adult
72% of travellers recommend
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- Boston Vacations
- Boston Museum of Fine Arts
- Axiom
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- 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.