Jamaica Plain Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Jamaica Plain

Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Price was CA $1,972, price is now CA $1,336 per person
CA $1,336
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.2/10 Wonderful! (2,404 reviews)
Great hotel from start to finish. Highly recommend

Reviewed on Mar 22, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,929, price is now CA $1,762 per person
CA $1,762
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure

Reviewed on Mar 30, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $6,088, price is now CA $3,918 per person
CA $3,918
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,479, price is now CA $1,673 per person
CA $1,673
per person
Jun 13 - Jun 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $5,096, price is now CA $3,521 per person
CA $3,521
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products.

Reviewed on Mar 29, 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

Downtown Boston

4.5/5(197 area reviews)

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.

Find hotels in Downtown Boston

Jamaica Plain Hotel Deals

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 CA $215 per night from Apr 5 to Apr 6
CA $215
CA $307 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (4,549 reviews)
Very nice

Reviewed on Mar 28, 2026

Omni Boston Hotel at the Seaport
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 CA $177 per night from Apr 5 to Apr 6
CA $177
CA $254 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (4,119 reviews)
Exceptionally kind staff

Reviewed on Apr 1, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Apr 6 to Apr 7
CA $247
CA $345 total
Apr 6 - Apr 7
includes taxes & fees
8.4/10 Very Good! (3,139 reviews)
The heater was so loud, I couldn’t sleep well.

Reviewed on Apr 1, 2026

Hilton Boston Park Plaza
See all 4,126 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Jamaica Plain vacation package cost?
Live it up in Jamaica Plain from as little as CA $1,336. 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.

Discover the most popular places to visit in Jamaica Plain

Arnold Arboretum

Arnold Arboretum

Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.

Arnold Arboretum

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.