Boston Holidays

Boston squeezes revolutionary history, big-league sport and the best seafood in America into one walkable harbourside city. This is the Massachusetts city break where you'll do more before lunch than most cities manage in a weekend.

Highlights of your Holidays to Boston

• Freedom Trail - Follow the red brick line for 2.5 miles past 16 revolutionary sites, from Boston Common to Paul Revere's House and the Old North Church

• Fenway Park - Catch the Red Sox at the oldest ballpark in Major League Baseball, home of the Green Monster and 37,000 of the loudest fans in sport

• The food - Lobster rolls on the harbour, creamy clam chowder, cannoli in the North End and oysters at the oldest restaurant in America

• Neighbourhood charm - Gas-lit lanes and cobbles on Beacon Hill, brownstones in Back Bay, and an Italian quarter that smells of fresh pasta and espresso

• The harbour - Whale-watching cruises, sunset sails and a waterfront that's been scrubbed up into one of the city's best hangouts

• Four proper seasons - Golden foliage in autumn, snow-dusted Christmas shopping, blossom in spring and beach-warm summers

Good to Know

• ☀️ Weather - Summers hit a gorgeous 25-28°C with low humidity by US standards, autumn is crisp and photogenic, and winters are properly snowy (pack a big coat, it's part of the fun)

• 💰 Money - A casual sit-down meal runs £20-£30 / €23-€35, a pint is £6-£8 / €7-€9, and a proper lobster roll is £20-£25 / €23-€29. Tip 18-20% in restaurants, and watch for nightly hotel facility fees at check-in

• 🌊 Fun Fact - In 1919 a storage tank burst and sent a two-storey wave of molasses through the North End at 35mph. Locals swear you can still smell it on hot summer days

Boston is perfect for you if...

• You want the big American city break without the big American sprawl (Boston is compact enough to cross on foot)

• You love history, you're the type who reads the plaque, and here the plaques are about actual revolutions

• You plan holidays around food, and a city that does lobster rolls, chowder and North End cannoli feels like destiny

• You've always fancied New England in the autumn, all golden leaves, harbour walks and cosy taverns

🏨 Hotels

Boston's hotels lean characterful: converted jails, gilded-age grand dames and harbour-view towers, most of them walkable to the sights. See all hotels in Boston or browse our top picks below...

👨‍👩‍👧‍👦 What are the best family hotels in Boston?

• Marriott Copley Place connects to the Copley Place and Prudential Center malls by covered skywalk, so you can reach shops, food courts and the View Boston observation deck without stepping into the weather. Big rooms and a pool seal it for families.

• Westin Boston Waterfront gives you Seaport space to spread out, an indoor pool for post-sightseeing wind-downs, and the Children's Museum a short walk along the water.

• Harborside Inn of Boston is a converted 1850s spice warehouse with exposed brick and beams, sitting between Faneuil Hall and the New England Aquarium, which is about as handy as Boston gets with kids in tow.

💑 What are the best hotels in Boston for couples?

• Liberty Hotel is the famous one: the old Charles Street Jail reborn as a soaring Beacon Hill stunner, where you drink cocktails under the original catwalks. Yes, the bar is called Clink.

• Omni Parker House is the oldest continuously operating hotel in America and the birthplace of the Boston cream pie. JFK proposed to Jackie in its restaurant, so the romance credentials are literally historic.

• Copley Square Hotel has been doing boutique Back Bay charm since 1891, with Copley Square's cafes and the Boston Public Library's gorgeous courtyard on the doorstep.

🎉 What are the best hotels in Boston for groups?

• W Hotel Boston drops you in the Theater District with a lobby bar built for pre-show drinks and Lansdowne Street's venues a short hop away.

• Westin Boston Waterfront works just as hard for groups: Seaport breweries and rooftop bars on your doorstep and plenty of room to regroup over breakfast.

• AC Hotel Boston Downtown is the sleek, modern, keep-it-simple base: sociable lounge, easy T access, and a price that leaves more in the kitty for game tickets.

✨ What are the best luxury hotels in Boston?

• Langham occupies the former Federal Reserve Bank, all marble, murals and afternoon tea, a short walk from the harbour and Quincy Market.

• Intercontinental Boston runs glassy floor-to-ceiling harbour views, a full spa and one of the best waterfront terraces in the city.

• Liberty Hotel earns a second mention for pure five-star theatre: the granite rotunda is one of America's great hotel lobbies, and rooms look over Beacon Hill or the Charles River.

👉 All hotels in Boston

Cheap holidays to Boston

Boston has a reputation as one of America's pricier cities, but a cheap Boston holiday is very doable if you play it smart. Flights are the biggest lever: January and February bring the lowest fares and a snow-globe-pretty city, while spring and late autumn pair kinder prices with milder sightseeing weather.

Once you land, the best of Boston is free. The Freedom Trail costs nothing to walk, Boston Common and the Public Garden cost nothing to wander, the Boston Public Library's courtyard is free to gawp at, and crossing the river for a stroll around Harvard's campus won't cost you a cent either. Even getting in from the airport is cheap: Logan sits barely three miles from downtown, so you're a quick T ride from your hotel rather than an expensive transfer.

Eat like a local and the food budget behaves too. Grab lunch from the stalls at Quincy Market, split a mountain of pasta in the North End, and save the big lobster blowout for one night instead of every night. One quirk worth knowing: Massachusetts charges no sales tax on clothes under about £130 / €150 per item, which makes Back Bay's shops dangerously good value.

Boston Holidays 2026/2027 - Travel Guide

👨‍👩‍👧‍👦 What are the best things to do on a Boston family holiday?

• Freedom Trail - Walk the 2.5-mile red brick line with a costumed guide who stays in character the whole way; kids love spotting the next marker before you do

• New England Aquarium - A four-storey ocean tank with sea turtles and reef sharks, plus penguins at eye level right by the harbour

• Boston Children's Museum - Three floors of climbing, building and splashing on the waterfront, perfect for burning off small-person energy

• Swan Boats - Pedal-powered and gloriously old-fashioned, gliding around the Public Garden lagoon as they have since 1877

• Fenway Park tour - Go behind the scenes at baseball's oldest park, walk the warning track and see the Green Monster up close even on non-game days

• Whale watching - Boats run from the harbour out to Stellwagen Bank, where humpbacks breach close enough to soak the front rows

💑 What are the best things to do for couples on a Boston holiday?

• Isabella Stewart Gardner Museum - A Venetian-style palace built around a flowering courtyard, complete with the empty frames from the world's biggest unsolved art heist

• Beacon Hill at dusk - Gas lamps flickering on, window boxes overflowing, and Acorn Street looking like it's posing for you

• North End evenings - Share fresh pasta on Hanover Street, then join the queue at Mike's Pastry for a cannoli to eat on the walk back

• Charles River Esplanade - Rent a kayak or just stroll the riverbank paths as the sailboats drift past the skyline

• View Boston - The observation deck on top of the Prudential Tower, best timed for golden hour with a cocktail in hand

• Frog Pond in winter - Skating under the lights on Boston Common is unapologetically festive and completely worth cold fingers

🎉 What are the top things to do for groups on a Boston holiday?

• A night at Fenway - Bleacher seats, ballpark franks and Sweet Caroline in the eighth inning; even non-baseball fans get swept up

• Duck Boat tour - Amphibious vehicles that trundle past the sights then splash straight into the Charles River, with tour guides who are half comedian

• Seaport crawl - Rooftop bars, harbour views and Harpoon Brewery's beer hall, where pretzels the size of your head soak up the IPA flight

• Quincy Market - A food hall in a colonnaded 1820s market building where everyone can grab something different and nobody has to compromise

• Lansdowne Street - The strip beside Fenway packs in music venues including House of Blues Boston, sports bars and late-night pizza

• Harbour cruise - Sunset sails and party boats leave from the wharves all summer; the skyline from the water is the best photo in town

More Destinations

• America - From New York's skyline to Florida's theme parks, Vegas neon to California surf, the USA does holidays on a scale nowhere else can match

• New York City - The city that never sleeps: Broadway shows, Central Park picnics, world-class museums and skyline views from the Empire State Building

• Orlando - The theme park capital of the world, where Disney, Universal and year-round sunshine make it the ultimate family blowout

• Las Vegas - Mega-resorts, world-famous shows, poolside days and the Grand Canyon on a day trip; nowhere on earth does spectacle like Vegas

• Miami - Art deco glamour, Cuban flavour and golden sand right against the city, with Latin nightlife that goes till sunrise

• Los Angeles - Hollywood, Venice Beach, Beverly Hills and taco trucks, the sprawling sunshine city where every neighbourhood is its own scene