Jamaica Plain Vacations from $583

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Your Jamaica Plain Vacation

Take all the stress out of planning your next escape by booking a Jamaica Plain vacation package. Soak in the sounds and sights of this enticing neighborhood and experience what it has to offer. Kick off your trip to Jamaica Plain with a visit to nearby attractions such as Fenway Park, Boston Museum of Fine Arts and Copley Place. Expedia will help turn your dream Jamaica Plain vacation into reality, no matter your travel plans or budget.

The Latest Jamaica Plain Vacation Packages

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (27 reviews)
Very good service. Furniture in all areas and the room is low and petite. Not comfortable. Bedding is comfortable. Food on Long Bar was well prepared. However presentation is pedestrian. Ordered Avacado Toast. Tasty, but arrived on a small plate. No garnish, no fruit etc. overall good stay.

Reviewed on Apr 8, 2024

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Jul 8 - Jul 12
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
7/10 Good! (75 reviews)
Stayed at Luxury Suites in East Boston for 3 nights. Zero communication about parking, we registered our vehicle with my credit card and got no proof of receipt or parking confirmation to enter the garage. Also were promised roof access which was untrue as the only access was in another building in the complex that we could not access. Only 1 of our 4 keys worked to get into the building and our room. The property also mentioned the apartment would be furnished with the necessary equipment, and the bare minimum was given (no sheet pans, coffee machine, ice maker, or spatula/mixing spoons, and only 2 rolls of toilet paper were provided along with no hand soap)

Reviewed on Jan 1, 2024

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9/10 Wonderful! (1,353 reviews)
Great property for our visit to Northeastern University. It was an easy taxi ride to the airport and an easy walk or subway ride to campus. Great shopping and dining across the street, and the hotel stored our luggage until our departure in the evening.

Reviewed on Apr 17, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
9/10 Wonderful! (148 reviews)
A bit expensive for what you get

Reviewed on Mar 31, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
May 22 - May 27
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
amazing staff and service, polite, friendly,

Reviewed on Apr 16, 2024

Prices and availability subject to change. Additional terms may apply.

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(2,415 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 hotel + flight trips in Downtown Boston

Jamaica Plain Hotel Deals

Bedrooms near Fenway & Downtown Boston
Bedrooms near Fenway & Downtown Boston
1.5 out of 5
182 Heath St, Boston, MA
The price is $125 per night from Apr 20 to Apr 21
$125
$190 total
includes taxes & fees
Apr 20 - Apr 21
3.2/10 (93 reviews)
"Don’t see anyone to check in or out with"

Reviewed on Nov 16, 2023

Bedrooms near Fenway & Downtown Boston
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $214 per night from Apr 21 to Apr 22
$214
$278 total
includes taxes & fees
Apr 21 - Apr 22
9/10 Wonderful! (1,868 reviews)
"Amazing hotel, great room. Will highly recommand."

Reviewed on Apr 15, 2024

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 $269 per night from Apr 21 to Apr 22
$269
$318 total
includes taxes & fees
Apr 21 - Apr 22
9.4/10 Exceptional! (2,113 reviews)
"Great location within walking distance of the Seaport's nightlife."

Reviewed on Apr 16, 2024

Seaport Hotel Boston
See all 3,296 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Jamaica Plain vacation package cost?
Live it up in Jamaica Plain from as little as $583. 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

Image for 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
Image for Faulkner Hospital

Faulkner Hospital

Though Faulkner Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Boston while you are here.

Faulkner Hospital
Image for Beth Israel Deaconess HealthCare-Jamaica Plain

Beth Israel Deaconess HealthCare-Jamaica Plain

Though Beth Israel Deaconess HealthCare-Jamaica Plain might be what brings you to town, perhaps you'll have a chance to explore more of Boston while you are here.

Beth Israel Deaconess HealthCare-Jamaica Plain

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

$177
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.