Jamaica Plain Holidays

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

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was €1,586, price is now €1,146 per person
€1,146
per person
26 Jun - 30 Jun
found 10 hours ago
Return flight included
Savannah (SAV) to Boston (BOS)
7.4/10 Good! (859 reviews)
Very nice and clean staff was very polite

Reviewed on 17 Mar 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was €2,115, price is now €1,440 per person
€1,440
per person
26 Jun - 30 Jun
found 10 hours ago
Return flight included
Savannah (SAV) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Everything advertised was correct and enjoyable relaxing.

Reviewed on 11 Apr 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was €2,465, price is now €1,724 per person
€1,724
per person
27 May - 1 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (535 reviews)
Loved all of it. Thank you to Jaclyn for a wonderful stay!

Reviewed on 7 Apr 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was €3,709, price is now €2,595 per person
€2,595
per person
26 May - 31 May
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (248 reviews)
The photos doesn’t give this place justice.

Reviewed on 24 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 €1,832, price is now €1,345 per person
€1,345
per person
27 May - 1 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,000 reviews)
Great location, easy to get to from the (free) shuttle to South Station. Easy check in, friendly staff. Reasonable restaurant attached in case you’re too tired to go out, and coffee places everywhere. Will stay there again

Reviewed on 11 Apr 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(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 €228 per night from 10 May to 11 May
€228
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,582 reviews)
Room was amazing Just not a lot of restaurants or bars around hotel

Reviewed on 11 Apr 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 €256 per night from 16 Apr to 17 Apr
€256
16 Apr - 17 Apr
includes taxes & fees
9.6/10 Exceptional! (4,179 reviews)
Great location. Amazing restaurants within walking distance. Easy to get to the Airport within 15 minutes

Reviewed on 11 Apr 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 €240 per night from 10 May to 11 May
€240
10 May - 11 May
includes taxes & fees
8.4/10 Very Good! (3,149 reviews)
Not what I was expecting. It was ok. I will not come back. Staff at the bar and other staff were very rude. Room was outdated. Bathroom was very, very small. Again, it was ok. Staff need training. Would not recommend and will not come back.

Reviewed on 11 Apr 2026

Hilton Boston Park Plaza
See all 4,228 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 €1,146. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.