Jamaica Plain Holidays

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Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was S$1,861, price is now S$1,358 per person
S$1,358
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,535 reviews)
We had a room with the bathroom inside. Nice size room, but no where for luggage or clothes. Close to a few spots to eat, train stop in walking distance about 15 minutes.

Reviewed on 27 Mar, 2026

Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
Save 100% on your flight
Price was S$5,745, price is now S$3,663 per person
S$3,663
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (1,522 reviews)
Amazing staff, room had great city view (beautiful at night). Very comfortable, very clean. Gym was fine for a couple days and they have an Equinox partnership if you need more machines.

Reviewed on 27 Mar, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was S$2,160, price is now S$1,440 per person
S$1,440
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
The room we stayed in was very very dark, very little natural light and lighting in the room was not fully functional. Room was also right on top and I mean right on top of the elevator, so pretty steady stream of noise into our room from there.

Reviewed on 27 Mar, 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was S$2,364, price is now S$1,700 per person
S$1,700
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,995 reviews)
Quiet and comfortable room in a great location. Room was smaller but cleanliness, service, and value were excellent.

Reviewed on 24 Mar, 2026

Cambridge Common House

Cambridge Common House

3.5 out of 5
West Cambridge
Price was S$1,873, price is now S$1,384 per person
S$1,384
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
No reviews

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 which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(95 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

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 5 Apr to 6 Apr
S$283
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (4,542 reviews)
nice location

Reviewed on 27 Mar, 2026

Omni Boston Hotel at the Seaport
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 S$298 per night from 10 Apr to 11 Apr
S$298
10 Apr - 11 Apr
includes taxes & fees
8.4/10 Very Good! (3,127 reviews)
The room was clean and comfortable. Location was excellent being able to walk to many food options.

Reviewed on 26 Mar, 2026

Hilton Boston Park Plaza
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 S$234 per night from 5 Apr to 6 Apr
S$234
5 Apr - 6 Apr
includes taxes & fees
9.6/10 Exceptional! (4,098 reviews)
Nice place very hard to find front door. Address does not take you to where you need to go

Reviewed on 27 Mar, 2026

Seaport Hotel Boston
See all 4,169 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 S$1,358. 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 which includes heritage elements

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

S$66
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

S$100
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

S$106
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Boston

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.