Jamaica Plain Vacation Packages
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Top Holiday Package Deals in Jamaica Plain
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
CA $1,412
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This hotel is one of, if not the, nicest hotels I have ever stayed at around the world. The level of service is second to none, and hotel itself, physically, is incredibly elegant. Being situated on Boston Harbor puts this hotel over the top and into a class of its own.
Reviewed on Oct 16, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,802
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
CA $1,527
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (3,468 reviews)
Big, no frills hotel, centrally located in DT Boston. Would have been better is they had a safe & small refrigerator. Rooms are small, but comfortable; beds were comfortable.
Reviewed on Oct 16, 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
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
Back Bay
1 out of top 10 points of interest in this area
Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.
Seaport District
1 out of top 10 points of interest in this area
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
Beacon Hill
1 out of top 10 points of interest in this area
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
North End
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
Jamaica Plain Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
CA $374
CA $493 total
Nov 11 - Nov 12
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $186
CA $217 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (2,976 reviews)
"Very clean comfortable and accomodating; great location!"
Reviewed on Oct 16, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
CA $241
CA $330 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (5,114 reviews)
"The location of this hotel was ideal for our visit. We planned a 2-day pre-cruise stay on our own. It's easy to take an Uber, taxi or Silver Line bus to the Flynn cruise port from this hotel. The room was comfortable, nicely appointed and had great western views over a park. It was quiet. The food ..."
Reviewed on Oct 16, 2026
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 vacation package cost?
Live it up in Jamaica Plain from as little as CA $1,234. 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 vacation package.
How do I get a cheap travel package to Jamaica Plain?
Our Jamaica Plain vacation packages promise plenty of savings for the savvy traveler. 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 cozy option is Luxury Apartment Boston Ma.
How far in advance should I book my Jamaica Plain vacation?
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 organizing your perfect Jamaica Plain getaway.
Can I choose my airline with a Jamaica Plain Expedia vacation 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 vacation 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 vacation 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 scene in this vibrant area.
Midway Café
After visiting Midway Café, make a plan to see the other sights and activities in Boston. Wander the forest 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 forest or discover the area's sunsets.
The Footlight Club
You can spend an afternoon exploring the galleries in The Footlight Club during your trip to Boston. Wander the forest or discover the area's sunsets.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.