Jamaica Plain Holidays

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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.
  • Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
    Jul 20 - Jul 27

    Hotel Ivy Boston Common + Flight

    Bay Village
    7 nights
    2.5 star property
    8.4/10 - Very good (1,470 reviews)
    "Staff were mostly nice, but overall one of the worst hotels I’ve ever stayed in. WiFi didn’t work for 3 days straight, the initial room I was in had blacked out windows, housekeeping doesn’t clean the rooms, the rooms are smaller than a jail cell, there is a 2 inch gap at the bottom of every door. It’s incredibly loud, the lift can be heard throughout the whole hotel every time someone uses it. If you have any other options, do not book this hotel"
    Reviewed May 30, 2026
    Return • London (LHR) - Boston (BOS)
    LHR - BOS • Direct BOS - LHR • Direct
    Save 100% on your flight
    £1,975
    £1,256
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillow-top beds, minibar
    Jul 20 - Jul 27

    Boston Harbor Hotel + Flight

    North End
    7 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Return • London (LHR) - Boston (BOS)
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    £3,671
    £1,971
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • Lobby
    Jul 20 - Jul 27

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    7 nights
    4.5 star property
    9.0/10 - Wonderful (1,244 reviews)
    "I recently stayed at the Fairmont Boston and unfortunately the property felt very outdated and not well maintained compared to what I expected from a Fairmont hotel. While the location is convenient and the staff were generally polite, the overall condition of the hotel needs significant updates. The rooms showed noticeable wear and tear, including older furniture, dated décor, and areas that did not feel particularly clean or refreshed. The hallways and common areas also felt tired and lacked..."
    Reviewed May 29, 2026
    Return • London (LHR) - Boston (BOS)
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    £3,146
    £2,051
    per traveller
    found 1 day ago
    Fairmont Copley Plaza, Boston
  • Front of property
    Jul 20 - Jul 27

    Eurostars The Boxer + Flight

    West End
    7 nights
    4.0 star property
    8.8/10 - Excellent (1,502 reviews)
    "Hotel was clean and kept in excellent condition, with helpful and friendly staff. Perfect place to stay for a city break and couldn't recommend it enough."
    Reviewed May 28, 2026
    Return • London (LHR) - Boston (BOS)
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    £2,327
    £1,633
    per traveller
    found 1 day ago
    Eurostars The Boxer
  • Property entrance
    Jul 20 - Jul 27

    Sea Crest Beach Resort + Flight

    North Falmouth
    7 nights
    3.5 star property
    8.0/10 - Very good (289 reviews)
    "The floors both in the room and down the walkway were dirty staff present but never seemed to clean never got a room cleaned had to ask for clean towels definitely a disappointment"
    Reviewed May 29, 2026
    Return • London (LHR) - Boston (BOS)
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    Save 100% on your flight
    £2,422
    £1,704
    per traveller
    found 1 day ago
    Sea Crest Beach Resort

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

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
The price is £223 per night from 7 Jun to 8 Jun
£223
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (4,659 reviews)
"The room was a little small and condensed without a separate bathroom area, but it was spectacular and the food amenities staff view were fantastic. Highly recommend and worth the price."

Reviewed on 30 May 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is £119 per night from 7 Jun to 8 Jun
£119
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (2,636 reviews)
"Loved it so much I came back for a second stay"

Reviewed on 30 May 2026

The Revolution Hotel
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 £248 per night from 28 Jun to 29 Jun
£248
28 Jun - 29 Jun
includes taxes & fees
9.6/10 Exceptional! (4,391 reviews)
"Clean room and the best hotel staff I have come across friendly and accommodating for little ones. Out little guy played "work" with a worker because she looked lonely by herself hm. From valet to the restaurant, all the employees are too of the line."

Reviewed on 30 May 2026

Seaport Hotel Boston
See all 4,214 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 , 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

£42
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£58
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£40
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
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.