Jamaica Plain Holidays

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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

Downtown Boston

4.5/5(17 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Our pick of the best Jamaica Plain Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is NZ$457 per night from 10 May to 11 May
NZ$457
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,576 reviews)
Clean, good food, good service. Cannot complain!

Reviewed on 9 Apr 2026

Omni Boston Hotel at the Seaport
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 NZ$359 per night from 12 Apr to 13 Apr
NZ$359
12 Apr - 13 Apr
includes taxes & fees
9.6/10 Exceptional! (4,157 reviews)
Room was spacious and clean, and staff was amazing.

Reviewed on 10 Apr 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
The price is NZ$467 per night from 10 May to 11 May
NZ$467
10 May - 11 May
includes taxes & fees
8.4/10 Very Good! (3,145 reviews)
Rooms could use an update and refresh

Reviewed on 9 Apr 2026

Hilton Boston Park Plaza
See all 4,225 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 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 fascinating museums and acclaimed art galleries in this vibrant area.

Axiom

Activities

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

NZ$89
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$143
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

NZ$135
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.