Jamaica Plain Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Game room
    Jul 28 - Jul 31

    Meco Hotel - Hostel + Flight

    West End
    3 nights
    2.0 star property
    8.6/10 - Excellent (423 reviews)
    "good"
    Reviewed May 19, 2026
    Roundtrip • Halifax (YHZ) - Boston (BOS)
    YHZ - BOS • Nonstop BOS - YHZ • Nonstop
    CA $2,104
    CA $1,151
    per traveller
    found 1 day ago
    Meco Hotel - Hostel
  • Breakfast meal
    Jun 24 - Jun 30

    By the Sea Guests Bed & Breakfast & Suites + Flight

    Dennis Port
    6 nights
    3.5 star property
    9.2/10 - Wonderful (185 reviews)
    "."
    Reviewed October 16, 2025
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $2,487
    CA $1,561
    per traveller
    found 1 day ago
    By the Sea Guests Bed & Breakfast & Suites
  • Reception
    Jul 5 - Jul 9

    The Inn at Hastings Park, Relais & Chateaux - Boston + Flight

    Lexington
    4 nights
    4.0 star property
    9.6/10 - Exceptional (256 reviews)
    "Splendid bed and breakfast"
    Reviewed April 29, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,359
    CA $1,487
    per traveller
    found 1 day ago
    The Inn at Hastings Park, Relais & Chateaux - Boston
  • Standard Room, 1 Queen Bed
    Jul 1 - Jul 5

    Hotel Ivy Boston Common + Flight

    Bay Village
    4 nights
    2.5 star property
    8.4/10 - Very good (1,451 reviews)
    "Safe, friendly staff, garage discount, great location. Easy check in and check out."
    Reviewed May 18, 2026
    Roundtrip • Halifax (YHZ) - Boston (BOS)
    YHZ - BOS • 1 stop BOS - YHZ • 1 stop
    CA $1,921
    CA $1,268
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Miscellaneous
    Jun 26 - Jul 1

    Raffles Boston + Flight

    Back Bay
    5 nights
    5.0 star property
    9.6/10 - Exceptional (264 reviews)
    "didn't meet expectation"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $5,646
    CA $3,865
    per traveller
    found 1 day ago
    Raffles Boston

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

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 $296 per night from May 22 to May 23
CA $296
CA $391 total
May 22 - May 23
includes taxes & fees
9.6/10 Exceptional! (4,369 reviews)
"Great staff! Friendly clean"

Reviewed on May 20, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 25 to May 26
CA $174
CA $203 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,615 reviews)
"Very cool hotel but beware of staying in the mezzanine floor - it is loud at night and you can’t get any sleep."

Reviewed on May 19, 2026

The Revolution Hotel
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 $246 per night from May 29 to May 30
CA $246
CA $343 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,657 reviews)
"Breakfast was nice its alacarte , pool very poor and no service on the pool , spa slots are very limited and they are off every Tuesday and Wednesday"

Reviewed on May 19, 2026

Omni Boston Hotel at the Seaport
See all 4,234 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 . 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 $79
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
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.