Commended Merchant - feefo
0208 290 9751
    Check our contact us page for our Christmas opening hours. Call or email us for great deals.
    Our travel experts are available and ready to take your call or click to email
    Our travel experts are available and ready to take your call or click to email
  • Our experts are available weekdays 9am-6pm and Saturdays 9am-5pm
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Booking an Infant?

Advanced Search Page >>


We are currently searching to find the best Flights and Hotels for your to holiday…

  • Massachusetts
  • Massachusetts
  • Massachusetts
  • Massachusetts
  • Massachusetts

​Holidays to Massachusetts​

Massachusetts has always been a happening kind of place. It's where the Pilgrim Fathers first settled, back in 1620; it's where the Boston Tea Party helped to ignite the American Revolution; it's where the USA's first university, Harvard, was founded.And it's a happening place still. With the must-see city of Boston at its heart, it's got beaches, islands, historic towns, rolling hills and a vibrant cultural scene - in fact everything you need for a fabulous holiday.

If it's sun, sea and sand you're after, then head to the North Shore and Cape Cod, or to the gorgeous islands of Nantucket and Martha's Vineyard. Cape Cod is New England's summer playground and has over 300 miles of fantastic golden beaches complete with dunes, tide pools and Atlantic surf. There's dozens of charming coastal communities to explore, including the Kennedys' favourite hangout of Hyannisport, and Wellfleet with its historic buildings and art galleries.

History is everywhere on holidays in Massachusetts, and there's plenty to discover. Boston's Freedom Trail takes in 16 crucial sites along the road to American independence, while at Plymouth you can pay homage to the Pilgrim Fathers at the spot where they first stepped ashore. Lexington Green is where the first shots of the Revolutionary War rang out, and at Old Sturbridge Village you can get a feel for what life for early settlers was really like.

To the west of the State you'll find the bustling college town of Pioneer Valley before you hit the Berkshires, which offer up a classic slice of New England rural life. Wooded hills and valleys are home to some charming towns like Stockbridge and Lenox, and waiting for the summer arts season to begin, or the Fall foliage to turn blazing red, is the order of the day.

Holidays in Massachusetts have something for everyone: just take your pick.

(read more...)


Don't Miss...


The Islands

Spend time on picture-postcard Nantucket and step back in time. As well as fabulous beaches, this old whaling island has over 800 historic buildings and Quaker sea captains’ homes. Upscale Martha's Vineyard is closer to the mainland and attracts a celebrity crowd who come for its pristine sands, picturesque lighthouses and gingerbread cottages. Don't miss the view from Aquinnah Cliffs.

The Arts

There's plenty by way of culture on holidays in Massachusetts. Top-class art is on show at Boston's Museum of Fine Art and at the cutting-edge MASS MoCA in North Adams. Meanwhile America's most revered international dance festival takes place in the Berkshires at Jacob's Pillow (14 June-24 August), while the Williamstown Theatre Festival (2 July-17 August) attracts a host of big names.


The state capital is a gem, and wandering among the parks and green spaces of its 'Emerald necklace' will only confirm the fact. There's a host of charming neighbourhoods to discover, and more first-rate museums and must-see historical sites than you can imagine. Don't forget to soak up the atmosphere of Harvard, or to drop by the Cheers bar.

Step Outdoors

Fancy white water rafting or kayaking? Then head for the Deerfield River. Parasailing more your kind of thing? Try Cape Cod's Gold Coast. Plus there's fishing on the Connecticut and Merrimack Rivers - hiking along the stunning Appalachian Trail. Its also worth remembering that Massachusetts is one of the world's top ten places for whale spotting.

Fabulous Food

With the ocean just a step away, fresh seafood rides high on the menu in Massachusetts, and a plate of clam chowder, lobster or fried clams is a must. Whether it's an upscale restaurant or a local shack you'll get a fantastic taste of the sea - before rounding off with a slice of Boston cream pie.

Twin Centre Holiday

Boston – Cape Cod

Combine two centres of American history on this suggested twin centre holiday, one a pulsating, cultural city, the other a bohemian enclave in a spectacular coastal setting. Start in Boston, where there's a museum or a historical site to discover round every corner, as well as captivating neighbourhoods to explore and stunning parks and gardens to wander in. Pick up a car from here and drive south along the Atlantic Coast to Cape Cod where you will have plenty of time to explore this famous corner of New England from your base in Provincetown, where the Pilgrims first landed in 1620.
Click here for more details


Fly Drive Holiday: Martha’s Vineyard & the Southern Coast

Boston– Falmouth –Martha’s Vineyard – Newport – Boston

Get away from it all and discover the famous resorts of Cape Cod, Martha’s Vineyard and Newport, Rhode Island on this relaxing New England fly drive holiday. Pick up your hire car in Boston and drive down to Falmouth on Cape Cod for a night before catching a ferry across to the celebrity island retreat of Martha’s Vineyard. After two days of beach walks, lighthouses and freshly caught seafood, it’s time to head back to the mainland and visit ‘America’s hometown’ Plymouth before stopping for a couple of nights in elegant Newport. Your holiday ends back in Boston with a few hours to spare before your flight home.
Click here for more details



Fly Drive Holiday: New England Six State Sampler

Boston– Ogunquit –North Conway – Stowe – Lenox – Mystic – Newport – Hyannis- Boston

For an introduction to the delights of New England, this six state sampler fly drive itinerary is hard to beat. Start in the region’s largest city, Boston before taking to the road and sampling the coastal wonders of Maine, the mountain vistas of New Hampshire, the charming rural scenery of Vermont, the antique shops of Connecticut, the revolutionary history of Massachusetts and the extravagant summer mansions of Rhode Island. Buzzing city life, history, culture, fantastic natural scenery and time for relaxing on the beach – what more could you want from a holiday?.
Click here for more details


Escorted Coach Tour: Colours of New England Holiday

Boston – Bar Harbor – White Mountains – Green Mountains – Newport – Cape Cod – Martha's Vineyard - Boston

This recommended escorted coach tour option will take you through some of the iconic sights of New England. Start in Boston, the cradle of American Liberty, before heading along the Maine coast to Bar Harbor and Acadia National Park. From here, you'll make your way inland to the undulating scenery of the White and Green Mountains before circling back to the coast via Newport and Cape Cod. There really is no better way to see the vibrant colours of New England than on this comprehensive escorted coach tour, with an expert guide on hand to highlight all the key attractions that you will see and experience along the way.
Click here for more details


Fly Drive Holiday: Best of New England

Boston – Kennebunkport – Bar Harbor – White Mountains – Stowe – The Berkshires – Newport – Cape Cod

Our suggested fly drive itinerary showcases the natural beauty and scenic vistas that only New England conjures. Start in Boston, the gateway to this region, steeped in history that effortlessly blends with modern city life. Then, take in the glorious Maine coastline for unforgettable views of the rugged cliffs and lighthouses that hug this state. Afterwards, drive inland for the breathtaking mountain ranges and scenic beauty of New Hampshire and Vermont Next, is the lively arts scene of The Berkshires in Massachusetts before Newport, Rhode Island. Your holiday finishes up in Cape Cod.
Click here for more details



Boston TV and Movie Sites Tour  
Enjoy a guided tour by coach to all the Boston sites you’ll recognise from your favourite TV shows and movies. A local actor will be your guide, giving you behind-the-scenes film details as you visit familiar buildings from TV shows such as Boston Legal, Ally McBeal and Cheers, as well as locations for films including Good Will Hunting, The Departed, Mystic River and Legally Blonde. Prices from £20 per person.

Fall Foliage Sightseeing Tour from Boston 
Marvel at the spectacular New England countryside on this scenic fall foliage tour from Boston. The tour takes you for a drive east over gently rolling hills and through small towns in Massachusetts and New Hampshire dotted with age-old taverns, colonial churches, farms and prairies, all featuring a beautiful display of autumn's stunning colours. From £31 per person. Note: This tour is seasonal and only operates from September through October.

Boston Photography Tour: Freedom Trail
Get your camera ready and explore Boston's Freedom Trail on this guided walking tour. Hear some interesting commentary from your guide, a professional photographer, and learn creative photography tips as you wind your way along the trail travelled by the Patriots in their fight for independence from British rule. From £30 per person.

Harvard Campus Walking Tour and Admission to Natural History Museum
During this 70-minute tour you’ll enjoy a one-of-a-kind presentation given by current Harvard students who share their insider perspective of college life in Cambridge. You'll see historical buildings as you tour Harvard Yard and Harvard Square, hear stories about the school's history and learn about some famous people who attended the school. From £13 per person.

You can add tickets for activities to your booking later.

Time Difference:
GMT- 5hours

Closest Airport:
Boston Logan International Airport (approx. 7 hours and 15 minutes, indirect flight)

Getting around:
If you’re staying in the state capital, Boston’s sights can be visited without a car. But if you want to get out and about on New England roads, why not hire a car to explore? Care hire is available from £21 per day.

Insider Tip:
The idyllic Cape Cod Rail Trail (starting in Dennis) runs 22 miles through forest, past cranberry bogs and along sandy ponds which are perfect for a dip. This rural route, historically used as a railway line, is one of the best bike trails in the whole of New England.

You’re going to need an ESTA:
For anyone travelling to the USA, the US authorities have imposed a requirement for passengers travelling under the Visa Waiver Programme (VWP), to register for Electronic Travel Authority. Just fill in the online application form which you can find at You will need to apply for entry via ESTA at least a minimum of 72 hours prior to travel.

View our interactive map

Deposits from £59pp 

Contact Us

Request a Quote
Request a Callback
Email Us

Why book with
My America Holiday

Fully Protected
  • 100% financial protection.
  • Tailor-made travel experts
  • 24 hour in-resort support.

My Caribbean 
​​ ​​​ ​

©1999 - 2020 My America Holiday 25/10/2020 11:34:21 CST. CST 2009218-20

View Terms & Conditions.

Please see our terms and conditions for more information.

Keyboard Instructions
change date: Ctrl/Command + ///
previous/next month: Page Up/Down
select date: Enter
cancel and close: Esc