Jamaica Plain Holidays

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Your Jamaica Plain Holiday

Book a Jamaica Plain holiday package and immerse yourself in the rhythm and vibe of this captivating neighbourhood. 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 holiday is simple with Expedia.

Our guide on 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 a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Our pick of the best Jamaica Plain Hotel Deals

ESJACPE GUEST HOUSE
ESJACPE GUEST HOUSE
2 out of 5
182 Heath St, UNIT 9, Boston, MA
The price is AU$307 per night from 16 June to 17 June
AU$307
16 June - 17 June
includes taxes & fees
2.8/10 (22 reviews)
"Well, I didn't have big things to complaint about, other than the bathroom zinc, the cold and the hot water cannot mix together. In the zinc, each one located separately. I understand that's an old building, but they still can change certain things."

Reviewed on 18 Nov. 2024

ESJACPE GUEST HOUSE
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 AU$456 per night from 2 July to 3 July
AU$456
2 July - 3 July
includes taxes & fees
9/10 Wonderful! (3,539 reviews)
"."

Reviewed on 15 Jun. 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$396 per night from 29 June to 30 June
AU$396
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (1,114 reviews)
"Great location, close to hub of Boston"

Reviewed on 11 Jun. 2025

Hilton Boston Back Bay
See all 3,708 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Jamaica Plain holiday package cost?
Live it up in Jamaica Plain from as little as . 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 holiday package.
How do I get a cheap travel package to Jamaica Plain?
Our Jamaica Plain holiday packages promise plenty of savings for the savvy traveller. 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 cosy option is Luxury Apartment Boston Ma.
How far in advance should I book my Jamaica Plain holiday?
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 organising your perfect Jamaica Plain getaway.
Can I choose my airline with a Jamaica Plain Expedia holiday 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 holiday 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 holiday 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

Axiom

You can study the exhibits at Axiom, a museum with a story of its own, during your travels to Boston. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Axiom

Activities

Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

AU$108
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$129
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
North End Boston Mafia Exploration Game and Tour

North End Boston Mafia Exploration Game and Tour

AU$17
per adult
90% of travellers recommend
North End Boston Mafia Exploration Game and Tour
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.