Jamaica Plain Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
€1,019
per person
27 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,940 reviews)
Enjoy hotel - nice location - a vibe - mostly shared bathroom down the hall but individual shower rooms and not that bad to deal with
Reviewed on 14 Oct 2026
Hyatt Regency Boston/Cambridge
MIT
€1,025
per person
27 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,665 reviews)
Here's a shorter version:
> The hotel was very clean, but I was disappointed with my stay. There was a loud noise in our room from the time we checked in, which made it difficult to sleep. Customer service sent someone to check it, and he said it was because the heat was set too high. He asked us to lower it and promised to bring a blanket, but the blanket never arrived.
Reviewed on 13 Oct 2026
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
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.
Back Bay
1 out of top 10 points of interest in this area
Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.
Seaport District
1 out of top 10 points of interest in this area
Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.
Beacon Hill
1 out of top 10 points of interest in this area
Lose yourself in the charming streetscapes, historic buildings and village-like atmosphere of Boston’s oldest and wealthiest suburbs.
North End
The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Old North Church or Paul Revere House while you're visiting, and jump aboard the metro at Aquarium to get around town.
Top hotels in Jamaica Plain
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
€311
11 Nov - 12 Nov
includes taxes & fees
9.2/10 Wonderful! (4,903 reviews)
"Omni was a great place to stay, within walking distance from both the Silver Line from the airport and to the Black Falcon cruise port. Every staff member was wonderful, helpful and generous. The place is huge, and gorgeous. On our return after our cruise, they let us pay a small fee to hold our ..."
Reviewed on 14 Oct 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
€134
1 Nov - 2 Nov
includes taxes & fees
9/10 Wonderful! (2,977 reviews)
"Enjoy hotel - nice location - a vibe - mostly shared bathroom down the hall but individual shower rooms and not that bad to deal with"
Reviewed on 14 Oct 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
€227
8 Nov - 9 Nov
includes taxes & fees
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 €1,019. 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.
Stay near popular Jamaica Plain attractions
Arnold Arboretum
Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.
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.
Midway Café
After visiting Midway Café, make a plan to see the other sights and activities in Boston. Wander the forests or discover the area's sunsets.
Southwest Corridor Park
You can take time to visit Southwest Corridor Park during your travels to Boston. Wander the forests or discover the area's sunsets.
The Footlight Club
You can spend an afternoon browsing the exhibits at The Footlight Club during your travels in Boston. Wander the forests or discover the area's sunsets.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
€44
per adult
90% of travellers recommend
View Boston Observation Deck General Admission
€30
per adult
Boston Harbor Narrated Sunset Cruise
€26
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.