Eastern Massachusetts Holidays from £905

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Your Eastern Massachusetts Holiday

Seize the opportunity for discovery with an Eastern Massachusetts holiday package. Head straight for Boston, where the dining and culture will be among the many highlights of your escape. With so many things to explore on a trip to Eastern Massachusetts, it can be tricky to know where to start. Kick off your travels in Boston at Fenway Park and TD Garden — two popular attractions here. Another top city worthy of a spot on your itinerary is Cambridge. Don't miss Fenway Park and TD Garden. Expedia has hotels, flights and whatever else you need to help you organise your own tailored Eastern Massachusetts holiday today.

Top Eastern Massachusetts Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Price was £1,340, price is now £905 per person
£905
per person
9 Jun - 15 Jun
found 22 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
7.2/10 Good! (1,194 reviews)
Property is good place and safe to stay

Reviewed on 16 Mar 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £5,746, price is now £3,689 per person
£3,689
per person
9 May - 16 May
found 18 hours ago
Return direct flight included
London (LGW) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on 14 Mar 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was £2,965, price is now £1,970 per person
£1,970
per person
22 May - 29 May
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (526 reviews)
Fantastic location, close to Mass Gen. Restaurant on property was also very good.

Reviewed on 19 Mar 2026

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
Price was £2,305, price is now £1,679 per person
£1,679
per person
22 May - 29 May
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
9/10 Wonderful! (1,015 reviews)
The room was spacious and clean. There was a microwave, mini fridge, hair dryer, and toiletries in the bathroom. Staff were friendly and helpful. The breakfast on-site was also very good. Highly recommend the chocolate chip pancakes.

Reviewed on 18 Mar 2026

Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Price was £1,810, price is now £1,346 per person
£1,346
per person
9 Jun - 15 Jun
found 22 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.6/10 Excellent! (1,247 reviews)
The staff was just wonderful! Shout out to Clara, she was so sweet. We were there to watch my grandson run at The Track at New Balance. This location was perfect!

Reviewed on 16 Mar 2026

Where to stay in Eastern Massachusetts

Find the best Eastern Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Massachusetts
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 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

Eastern Massachusetts Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)

Top hotels in Eastern Massachusetts

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 £162 per night from 22 Mar to 23 Mar
£162
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (4,520 reviews)
Clean room, great location and staff

Reviewed on 20 Mar 2026

Omni Boston Hotel at the Seaport
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 £158 per night from 5 Apr to 6 Apr
£158
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (3,119 reviews)
Highly recommend

Reviewed on 19 Mar 2026

Hilton Boston Park Plaza
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 £125 per night from 5 Apr to 6 Apr
£125
5 Apr - 6 Apr
includes taxes & fees
9.6/10 Exceptional! (4,065 reviews)
The staff was so nice and friendly! Great hotel!

Reviewed on 19 Mar 2026

Seaport Hotel Boston
See all 16,125 properties in Eastern Massachusetts
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

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(62 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(104 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(205 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Eastern Massachusetts

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

£13
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

£13
per traveller
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

£37
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Eastern Massachusetts

Frequently asked questions

Can I cancel my flight booking to Eastern Massachusetts due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for most travel queries, including about flight changes due to COVID-19. For greater peace of mind, look over the terms and conditions of your preferred carrier before booking.
What's the best way to find cheap flights to Eastern Massachusetts that have flexible change policies?
When it comes to travelling these days, flexibility is key. That's why we've added a "No change fee" filter to help you find flexible, low-priced flights to Eastern Massachusetts. It's to the left of your screen just underneath the "Flexible change policies" subheading.
What are some of the general tips for travellers to Eastern Massachusetts during the COVID-19 outbreak?
With new safety guidelines in place, travel looks a bit different these days. Here's what you should know before you get on that plane to Eastern Massachusetts:
  • Find out if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any special conditions you'll need to follow on arrival, such as mandatory quarantining.
  • Keep your face mask on during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • Rather than handing a TSA employee your boarding pass, position it straight on the scanner yourself. When that's done, hold it up for inspection.
  • You can take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray screening.
  • Remove items from your pockets, such as your wallet and phone, and place them in your carry-on instead of the bins. This will reduce handling during the screening process.
  • If you're taking food on board, put it in a clear plastic bag and then into a scanning bin. This lessens the likelihood that a TSA employee will need to handle your carry-on bag or food container for closer inspection.

Which airlines fly to Eastern Massachusetts?
Cape Air offers flights into or near Eastern Massachusetts, including 1785 that touch down at Logan Intl. Airport (BOS) each month. Choose your holiday dates and then secure your airfare early to get the best deal.
How can I find cheap tickets to Eastern Massachusetts?
One of the easiest ways to snare cheap tickets to Eastern Massachusetts is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll reveal the cheapest prices for nearby days. The best price for a flight to Eastern Massachusetts in the last seven days was . Booking well ahead of time will usually help you pick up an even better deal.
How much is a flight to Eastern Massachusetts?
One-way flights departing from () sold for just in the last seven days. During this time, the price of a return air ticket to Eastern Massachusetts varied between and . If you spot a good deal, grab it quickly — these prices don't stick around for long.
What are the most popular airports to fly into in Eastern Massachusetts?
Start organising your Eastern Massachusetts trip by securing a seat on one of the 12051 monthly flights to Logan Intl. Airport (BOS). This is the region's main point of entry.
When is the cheapest time to fly to Eastern Massachusetts?
If you'd rather spend your cash on having fun in Eastern Massachusetts rather than on flying there, take off early in the week. The cheapest day to travel is usually Tuesday, followed by Monday. With many people travelling on weekends, Saturday often has the most expensive fares.
How much is a plane ticket to Eastern Massachusetts?
Flights to Eastern Massachusetts ranged from to in the last seven days. Generally, the earlier you make a reservation, the bigger the bargain.
Which airlines with flights to Eastern Massachusetts employ COVID-19 cleanliness policies?
As travel restrictions start to lift, many airlines are now servicing flights with new strategies including physical distancing and enhanced disinfection measures. Here's what multiple carriers are doing to help stop the spread of COVID-19:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.