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A street lined with historic buildings, including the Union Oyster House and Yankee Publishing Building.

Boston Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Where to stay in Boston

Find the best Boston areas for the activities you enjoy most.
A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

Back Bay showcases Boston's architectural grandeur with Victorian brownstones lining Commonwealth Avenue and upscale shops on Newbury Street. The area borders the Public Garden, offering peaceful green space amid the city buzz. Historic landmarks like Trinity Church and the Boston Public Library give the area its distinguished character. Easily navigate this refined district using the Green Line at Copley, Prudential, or Arlington stations. Luxury boutiques and fine dining options cater to sophisticated tastes. The vibrant shopping scene balances perfectly with cultural attractions and the neighborhood's elegant residential charm.

A brick building with a flag, a street lamp, and greenery.

Beacon Hill

Beacon Hill captivates visitors with its historic charm and elegant Federal-style terrace houses. Gas-lit streets and brick pavements transport you back to 19th-century Boston. The gold-domed Massachusetts State House stands proudly at the neighborhood's crown. Charles Street offers upscale boutiques and cosy bistros for sophisticated shoppers. The area balances luxury with authentic residential character. Acorn Street's narrow cobblestones create perfect photo opportunities for architecture enthusiasts. Despite its central location, the area maintains a tranquil atmosphere away from city bustle. Boston Common and Public Garden are just steps away for nature lovers.

A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

City centre Boston weaves America's revolutionary storey into a vibrant urban hub. The Freedom Trail guides visitors past iconic sites like Faneuil Hall and the Old State House. Historic cobblestone streets lead to ancient burial grounds nestled between gleaming financial towers. South Station connects travellers to the entire city. Explore the New England Aquarium or catch harbour views along the scenic Harborwalk. Hop on the T at State Street or City centre Crossing stations for easy city access. After dark, colonial-era taverns serve up authentic Boston flavour alongside modern eateries. Suffolk University adds youthful energy to this walkable district.

A large, illuminated ship docked at a pier with fireworks in the background.

Seaport District

Boston's Seaport District dazzles with its waterfront promenade and harbour views. This former industrial area now buzzes with contemporary art at the ICA and maritime history at the Tea Party Ships & Museum. The area balances sleek glass towers with wide pedestrian walkways lined with public art. Spend evenings enjoying waterfront dining or catching concerts at Leader Bank Pavilion. Harbour walks reveal stunning city skyline panoramas while water taxis connect you to city centre. The area's modern vibe makes it perfect for travellers seeking urban sophistication with ocean breezes.

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

North End

Boston's North End pulses with Italian heritage through its narrow, winding streets. The aroma of fresh cannoli fills the air as you stroll past historic red-brick buildings. Paul Revere's House and Old North Church stand as reminders of America's revolutionary past. Follow the Freedom Trail markers along cobblestone streets to discover hidden trattorias and small bakeries. The area opens to Boston Harbour views where waterfront paths offer peaceful escapes. Everything feels accessible by foot, creating a European village atmosphere right in the heart of Boston.

Discover the most popular places to visit in Boston

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Step into America's oldest ballpark where the Green Monster wall and century of baseball history await. Catch a guided tour for behind-the-scenes access to this iconic Red Sox sanctuary.

Boston Hotel Deals

Bar (on property)

citizenM Boston Back Bay

citizenM Boston Back Bay
4.0 star property
2.7 km from Boston
9.4 out of 10, Exceptional, (2,890 reviews)
"Loved the location! Would absolutely stay again!"
The price is S$284
includes taxes & fees
9 Aug - 10 Aug
citizenM Boston Back Bay
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.
See all properties in Boston

Frequently Asked Questions

How much does a Boston holiday package cost?

You'll find cheap prices on Expedia for your Boston escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Boston costs.

What are the cheapest months to go to Boston?

December, January and February are great times to look for cheap Boston holiday packages. Opting to travel in less busy months means you can typically find lower prices on hotels and flights.

How many days is enough for Boston?

Dedicate at least 2 days for your Boston holiday to really discover everything that makes this destination special. Wander around popular neighbourhoods, including South Boston and D Street - West Broadway. Then make a beeline for top attractions like Boston Museum of Fine Arts and Museum of Science. With a well-planned itinerary, you can keep busy with room for some rest and relaxation too. Want to venture outside of Boston? Consider a day trip or two.

Is it worth booking a holiday package to Boston?

It's no wonder a Boston holiday is on the must-do list of many travellers. Popular attractions like Fenway Park are just the start of what you can explore here.

How to find the best Boston package deals?

Start your search for a Boston package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Boston package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Boston adventure off to a flying start.

Is it cheaper to book a Boston holiday as a package?

You can enjoy significant savings on your next Boston retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a holiday package to Boston?

Secure incredible discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Boston adventure.

How to plan a trip to Boston?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Boston.
  2. Set a budget: Consider expenses such as flights, food and transportation when working out how much to put aside for your trip to Boston. Then, pick a hotel that suits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide how long to go away for: Now that you're more familiar with Boston, you can figure out the right length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Boston holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.