Jamaica Plain Vacations from ￥163,264

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The Latest Jamaica Plain Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Boston Downtown - Seaport

Cambria Hotel Boston Downtown - Seaport

3.5 out of 5
South Boston
Price was ￥184,860, price is now ￥163,264 per person
￥163,264
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,004 reviews)
Great location, nice hotel

Reviewed on Sep 24, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was ￥296,846, price is now ￥231,490 per person
￥231,490
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.

Reviewed on Sep 17, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥699,339, price is now ￥578,730 per person
￥578,730
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on Sep 15, 2025

Boston Marriott Long Wharf

Boston Marriott Long Wharf

4 out of 5
North End
Price was ￥236,414, price is now ￥198,302 per person
￥198,302
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,004 reviews)
Great location. Inside it is very dark and a bit sad when outside it is sunny. Overall it is a pity not to take advantage of the sea side and have a terrace setup to enjoy a drink or coffee.

Reviewed on Sep 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥660,765, price is now ￥562,918 per person
￥562,918
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The view is great Restaurant is superb

Reviewed on Sep 24, 2025

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 which includes night scenes and a city as well as a small group of people

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.

Find hotels in Downtown Boston

Jamaica Plain Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥34,824 per night from Oct 5 to Oct 6
￥34,824
￥40,554 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (3,821 reviews)
"Most of the staff were great, though when we were checking in during the pouring rain, we asked about parking and the person was basically clueless, they told us of an app that had me park a half hour walk away, so I walked in the rain, luckily I found a bar to warm up in and have a drink!! lol. ..."

Reviewed on Sep 22, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥40,926 per night from Sep 28 to Sep 29
￥40,926
￥48,402 total
Sep 28 - Sep 29
includes taxes & fees
9.6/10 Exceptional! (3,476 reviews)
"The staff is always so accommodating. The room was clean and comfortable. We love the pool and accessibility the hotel has to area attractions."

Reviewed on Sep 24, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥38,614 per night from Oct 5 to Oct 6
￥38,614
￥51,033 total
Oct 5 - Oct 6
includes taxes & fees
9/10 Wonderful! (4,050 reviews)
"I like the space and views"

Reviewed on Sep 24, 2025

Omni Boston Hotel at the Seaport
See all 3,787 properties in Jamaica Plain
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.

Frequently asked questions

How much does a Jamaica Plain vacation package cost?
Live it up in Jamaica Plain from as little as ￥163,264. We offer a great selection of hotels, flights and rental cars to suit every budget and style. You can pick up even better deals when you add some experiences or tours to your vacation package.
How do I get a cheap travel package to Jamaica Plain?
Our Jamaica Plain vacation packages promise plenty of savings for the savvy traveler. For the best deals, simply combine your hotel, flights and tours into a budget-friendly package. But low prices are only the start of your next unforgettable adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 properties throughout the world to pick from. Whatever your style or budget, there's a package here just for you.
Where should I stay in Jamaica Plain?
A trip to Jamaica Plain isn't complete without stopping by Fenway Park and TD Garden. Reserve a room as close as possible for easy access to these terrific attractions.
What are the top hotels in Jamaica Plain?
Get your trip off to a great start by reserving a room at Wyman Bed And Breakfast. It's one of most popular hotels in Jamaica Plain. Another cozy option is Luxury Apartment Boston Ma.
How far in advance should I book my Jamaica Plain vacation?
It's difficult to pick the perfect time for airfares, but we normally say the earlier, the better. Many international journeys on Expedia become available to compare up to a year in advance. If you're booking last minute, don't stress. Cheap prices appear from time to time within a few weeks of departure dates.
What does an Expedia Jamaica Plain travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add tours and activities. Want to pick your fare class? That's also possible. The choice is all yours when it comes to organizing your perfect Jamaica Plain getaway.
Can I choose my airline with a Jamaica Plain Expedia vacation package?
You can. Expedia has access to more than 550 airline partners worldwide, so pick the carrier that fits your needs.
If I'm not able to travel, can I cancel my Jamaica Plain vacation package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Jamaica Plain vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Jamaica Plain

Arnold Arboretum which includes heritage elements

Arnold Arboretum

Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.

Arnold Arboretum

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,728
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥8,084
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

￥5,048
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.