Jamaica Plain Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by throwingsofas

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

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is 3.050.179 ₫ per night from 20 Jan to 21 Jan
3.050.179 ₫
3.551.933 ₫ total
20 Jan - 21 Jan
includes taxes & fees
9.2/10 Wonderful! (6,144 reviews)
The staff was so nice and the check-in was easy. It was a nicely decorated boutique hotel that I would definitely stay in again. It was close to absolutely everything; the Freedom Trail, North End, Harbor, Boston Common, and there was a subway station immediately outside of the hotel. The only downside ...

Reviewed on 14 Jan 2026

Harborside Inn Of Boston
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is 10.377.440 ₫ per night from 22 Jan to 23 Jan
10.377.440 ₫
12.084.528 ₫ total
22 Jan - 23 Jan
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
No complaints , everything . I would go back again and again.

Reviewed on 12 Jan 2026

The Langham, Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is 5.789.035 ₫ per night from 17 Feb to 18 Feb
5.789.035 ₫
6.466.352 ₫ total
17 Feb - 18 Feb
includes taxes & fees
9.6/10 Exceptional! (3,516 reviews)
The hotel was beautiful and the staff was top notch!

Reviewed on 17 Jan 2026

Encore Boston Harbor
See all 4,011 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
Gillette Stadium

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
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 acclaimed theatre scene.

Harvard University