Jamaica Plain Holidays

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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(94 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 Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in Jamaica Plain

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 S$268 per night from 25 Nov to 26 Nov
S$268
includes taxes & fees
25 Nov - 26 Nov
9.6/10 Exceptional! (2,605 reviews)
"Great hotel, room service, $40 parking"

Reviewed on 3 Nov,2024

Seaport Hotel Boston
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$272 per night from 27 Nov to 28 Nov
S$272
includes taxes & fees
27 Nov - 28 Nov
8.6/10 Excellent! (2,867 reviews)
"Love this place!"

Reviewed on 4 Nov,2024

Omni Parker House
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$299 per night from 25 Nov to 26 Nov
S$299
includes taxes & fees
25 Nov - 26 Nov
9.2/10 Wonderful! (4,863 reviews)
"Def recommend!"

Reviewed on 4 Nov,2024

The Dagny Boston
See all 3,254 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.

Popular places to visit

Image for Arnold Arboretum

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

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$97
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

S$33
Per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Image for Boston Harbor New England Aquarium Whale-Watching Cruise

Boston Harbor New England Aquarium Whale-Watching Cruise

S$105
Per adult
86% of travellers recommend
Boston Harbor New England Aquarium Whale-Watching Cruise
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.