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

Downtown Boston

4.5/5(95 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

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 4.454.904 ₫ per night from 10 May to 11 May
4.454.904 ₫
6.086.089 ₫ total
10 May - 11 May
includes taxes & fees
9.6/10 Exceptional! (4,200 reviews)
Staff went above and beyond to make the stay fabulous.

Reviewed on 19 Apr 2026

Seaport Hotel Boston
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 4.902.856 ₫ per night from 10 May to 11 May
4.902.856 ₫
6.782.873 ₫ total
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,584 reviews)
Clean room and food was very fresh. Staff were very friendly and helpful

Reviewed on 19 Apr 2026

Omni Boston Hotel at the Seaport
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is 5.428.056 ₫ per night from 26 Apr to 27 Apr
5.428.056 ₫
6.320.971 ₫ total
26 Apr - 27 Apr
includes taxes & fees
9.2/10 Wonderful! (6,469 reviews)
No desk was provided for my room when purchased stay.

Reviewed on 19 Apr 2026

Harborside Inn Of Boston
See all 4,235 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

Fenway Park

4.5/5(62 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(104 reviews)

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
Gillette Stadium

Gillette Stadium

3/5(2 reviews)

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

Gillette Stadium