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.
Four Seasons Hotel Boston
Bay Village
CA $4,803
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
It was our first visit to Boston. So glad we stayed at the Four Seasons on Boylston. It’s centrally located to all the attractions that were on our list. The city view trolley is located across the street from the hotel. Easy hop on and off. Staff were amazing - friendly and professional. We will definitely stay here again when we come back to Boston.
Reviewed on Aug 6, 2026
Sesuit Harbor House
CA $987
per person
Sep 16 - Sep 20
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (196 reviews)
The Sesuit Harbor House is awesome. Has a very Cape Cod feel, the owners are excellent very attentive and have done an awesome job with this property. There is a beautiful fire pit, pool, nice outside areas to eat and relax and they also have goats! I highly recommend, close to dining and beaches as well.
Reviewed on Aug 1, 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
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
1 out of top 10 points of interest in this area
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
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $264
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (4,702 reviews)
"Very polite staff. Very nice place to stay if you like views by the water. Very convenient place to go and get food and very close to the TD Garden for events. Thank you so much !"
Reviewed on Aug 8, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $190
CA $221 total
Aug 27 - Aug 28
includes taxes & fees
9/10 Wonderful! (2,811 reviews)
"Everything is good"
Reviewed on Aug 8, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $328
CA $439 total
Aug 20 - Aug 21
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 vacation package cost?
Live it up in Jamaica Plain from as little as CA $700. 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.
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.
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.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $48
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.