Jamaica Plain Holidays

Book a Hotel + Flight or Car together to unlock savings

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 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

Top hotels in Jamaica Plain

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
8.8/10 Excellent! (2,163 reviews)
"Interesting hotel in great location. Not exactly what we expected, but fine. Bath amenities and robes were great."

Reviewed on 10 Oct 2025

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The Revolution Hotel
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 5.771.745 ₫ per night from 9 Nov to 10 Nov
5.771.745 ₫
6.721.316 ₫ total
9 Nov - 10 Nov
includes taxes & fees
9.2/10 Wonderful! (3,926 reviews)
"Great hotel!"

Reviewed on 14 Oct 2025

citizenM Boston North Station
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 8.347.360 ₫ per night from 19 Oct to 20 Oct
8.347.360 ₫
10.640.605 ₫ total
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (6,598 reviews)
"Helpful and friendly staff. Close to everything!"

Reviewed on 13 Oct 2025

The Dagny Boston
See all 3,804 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 1null000null000 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

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its fascinating museums.

Harvard University
New England Aquarium

New England Aquarium

Take the family to visit the sea creatures at New England Aquarium, and learn why this is a favourite attraction in Boston. Stroll along the waterfront or attend a sporting event in this vibrant area.

New England Aquarium