Jamaica Plain Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was €1,655, price is now €1,108 per person
€1,108
per person
8 Oct - 12 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on 21 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was €2,798, price is now €1,518 per person
€1,518
per person
8 Oct - 12 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
The staff were amazing, rooms were spotless and with wonderful amenities and special touches.

Reviewed on 22 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was €2,442, price is now €1,475 per person
€1,475
per person
8 Oct - 12 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on 20 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was €1,680, price is now €1,138 per person
€1,138
per person
8 Oct - 12 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,073 reviews)
Location was amazing. Facilities were clean and staff was friendly. My only complaint is that the pool area was a loud party scene, so much so that I couldn’t spend very long there. Since this was the main reason I chose this hotel over others and paid the $30 plus taxes “resort fee” on top of the regular cost this was disappointing.

Reviewed on 21 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was €2,173, price is now €1,494 per person
€1,494
per person
8 Oct - 12 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

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 featuring a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

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.

Find hotels in Downtown Boston

Top hotels in Jamaica Plain

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €215 per night from 1 Sept to 2 Sept
€215
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (3,850 reviews)
It’s okay
"It was cool but the elevator button didn’t work for my floor. There is also a lot of ghetto people enjoying being hood rich for a weekend, be aware."

Reviewed on 18 Aug 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is €174 per night from 24 Aug to 25 Aug
€174
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,689 reviews)
Hands down AMAZING
"Our stay was amazing from start to finish! The check in staff was super helpful. Our room was ready earlier than expected which was great after travel. The hotel was close to everything, great food, great shopping and of course right beside TD Garden. The best part was the view from our room. Get ..."

Reviewed on 20 Aug 2025

citizenM Boston North Station
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 €146 per night from 1 Sept to 2 Sept
€146
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,260 reviews)
"Wonderful area!"

Reviewed on 20 Aug 2025

Seaport Hotel Boston
See all 3,776 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.

Frequently asked questions

How much does a Jamaica Plain holiday package cost?
Live it up in Jamaica Plain from as little as €1,108. 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.

Popular places to visit

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

Axiom

You can study the exhibits at Axiom, a museum with a story of its own, during your travels to Boston. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Axiom

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€61
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€29
per adult
84% 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.