Jamaica Plain Holidays from £1,257

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Your Jamaica Plain Holiday

Take all the stress out of planning your next escape by booking a Jamaica Plain holiday package. Soak in the sounds and sights of this enticing neighbourhood 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 holiday into reality, no matter your travel plans or budget.

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was £1,879, price is now £1,257 per person
£1,257
per person
23 May - 29 May
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Value for money. Short work into downtown Boston with the business district and tourist attractions.

Reviewed on 14 Apr 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was £3,854, price is now £2,603 per person
£2,603
per person
16 Jun - 21 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!

Reviewed on 13 Apr 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £4,505, price is now £3,051 per person
£3,051
per person
16 Jun - 21 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (248 reviews)
The photos doesn’t give this place justice.

Reviewed on 24 Mar 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was £2,593, price is now £1,837 per person
£1,837
per person
23 May - 29 May
found 1 day ago
Return flight included
London (LHR) 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

Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Price was £1,805, price is now £1,316 per person
£1,316
per person
23 May - 29 May
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.4/10 Exceptional! (2,029 reviews)
Fenway view is cool by day, but flashing neons at night is less so. Valet is crazy expensive.

Reviewed on 13 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 £194 per night from 10 May to 11 May
£194
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (4,599 reviews)
Room was amazing, concier

Reviewed on 14 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 £164 per night from 10 May to 11 May
£164
10 May - 11 May
includes taxes & fees
9.6/10 Exceptional! (4,197 reviews)
Only stayed for one night didn’t use any of the amenities. Room was clean

Reviewed on 14 Apr 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
The price is £204 per night from 10 May to 11 May
£204
10 May - 11 May
includes taxes & fees
8.4/10 Very Good! (3,161 reviews)
Clean room great location

Reviewed on 14 Apr 2026

Hilton Boston Park Plaza
See all 4,225 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Jamaica Plain travel package cost?
Starting from as low as £1,257, you can build your own Jamaica Plain package the way you want. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Jamaica Plain travel package?
Yes, you can. We realise life happens, so we're happy to help if you need to make changes to your Jamaica Plain travel package. You may be able to change or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Jamaica Plain?
Imagine all the thrilling things you could do in Jamaica Plain with extra cash in your pocket. Watch your savings stack up when you combine your travel bookings into a Jamaica Plain travel package. You have loads of choice when it comes to booking with Expedia too. In fact, you can choose from over 550 air carriers and 1,000,000 properties around the globe. Whether you're heading off with the whole family or flying solo, organising a trip to Jamaica Plain is better with a package.
Does Expedia offer Book Now, Pay Later Jamaica Plain holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply choose the payment plan best suited to your needs during the checkout process and take the stress out of budgeting for your trip. Remember to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budget sizes, so you can escape on that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip in multiple transactions.
  • Low deposit holidays: When you spot an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your getaway.

Where should I stay in Jamaica Plain?
Travellers come from all corners of the globe to experience Fenway Park and TD Garden in Jamaica Plain. Book yourself a room close to these top attractions to make sightseeing a breeze.
What are the top hotels in Jamaica Plain?
Boston Park Plaza and Embassy Suites Boston Logan Airport are two of the most sought-after properties in Jamaica Plain. Why not check out the rates and amenities at each and then make up your mind?
How far in advance should I book my Jamaica Plain holiday?
While not all airlines release tickets early, you can normally look up international flights on Expedia up to a year in advance. This is the time you can score some incredible deals. If you're booking late, you could still be in luck. Sometimes the cheapest prices become available only weeks before departure.
What does an Expedia Jamaica Plain travel package include?
It comes down to what you're looking for. If you're travelling by yourself, you might decide to combine hotels and flights. Bringing the entire family to Jamaica Plain? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Jamaica Plain travel package?
You'll pick up amazing savings when you combine your hotels, flights and rental cars into a package. Not only that, booking everything together will make your trip planning easier. So why waste your money or time? Whether you're organising a luxury romantic escape or a low-cost family road trip, have a look at our package deals today.
Can I choose my airline with a Jamaica Plain Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our travel packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.

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

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

£39
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

£63
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

£17
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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. Flight-inclusive packages are ATOL protected.