Jamaica Plain Holidays from £929

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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.
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was £1,304, price is now £929 per person
£929
per person
27 Aug - 2 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
8.4/10 Very good! (223 reviews)
Hotel is clearly a bit older and not well insulated so you can hear everything from the rooms surrounding you. The rooms also have connecting doors to each other that while they can lock was an unpleasant surprise given the screaming child having a meltdown at 7:30AM and the lack of sound proofing. Would not ever plan on staying there again. It was a more affordable option but not worth it. Also there isn't enough parking for their location so if you get in late you may not have a spot.

Reviewed on 14 Jul 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,463, price is now £1,484 per person
£1,484
per person
27 Aug - 2 Sept
found 14 hours ago
Return flight included
London (LGW) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Love coming back to a refreshed clean room after a long hot day of sightseeing.

Reviewed on 15 Jul 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was £1,524, price is now £1,041 per person
£1,041
per person
27 Aug - 2 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.

Reviewed on 12 Jul 2026

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was £1,428, price is now £1,014 per person
£1,014
per person
27 Aug - 2 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.6/10 Exceptional! (185 reviews)
What a hidden gem! We were looking for an overnight on the Cape close to all our favorite places and this was the perfect place. Host so incredibly gracious - hospitality is alive at this place! The room was clean and spacious, the grounds immaculate and beautiful- pool and Adirondack chairs. The picnic basket in the morning was such a fun and delicious treat. We will be back!

Reviewed on 15 Jul 2026

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Save 100% on your flight
Price was £2,459, price is now £1,781 per person
£1,781
per person
29 Aug - 5 Sept
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (394 reviews)
Gym was very limited Everything else was very good

Reviewed on 29 Jun 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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

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 £196 per night from 26 Jul to 27 Jul
£196
26 Jul - 27 Jul
includes taxes & fees
9.6/10 Exceptional! (4,597 reviews)
"Valet people great. Hotel front desk staff not rude but just not pleasant either. Called front desk multiple times and no answer."

Reviewed on 15 Jul 2026

Seaport Hotel Boston
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 £140 per night from 16 Aug to 17 Aug
£140
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (2,737 reviews)
"Cutest studio. Super clean. Most comfortable bed of all the hotels I have stayed at. No breakfast included but there are plenty of amazing options in the neighborhood."

Reviewed on 15 Jul 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundable
The price is £146 per night from 16 Aug to 17 Aug
£146
16 Aug - 17 Aug
includes taxes & fees
Hyatt Regency Boston/Cambridge
See all 4,241 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 £929, 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.

Stay near popular Jamaica Plain attractions

Arnold Arboretum

Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.
See properties

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
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

£36
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£60
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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. Flight-inclusive packages are ATOL protected.