Boston Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Boston

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is S$175 per night from 27 Jul to 28 Jul
S$175
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (2,910 reviews)
"Nice"

Reviewed on 18 Jul, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is S$210 per night from 1 Aug to 2 Aug
S$210
1 Aug - 2 Aug
includes taxes & fees
9/10 Wonderful! (1,548 reviews)
"I enjoy staying at Omni hotels and this stay was on part"

Reviewed on 15 Jul, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is S$186 per night from 27 Jul to 28 Jul
S$186
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,332 reviews)
"It was wonderful! The bar/ restaurant was excellent (recommend the smash burgers)!"

Reviewed on 18 Jul, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,728 properties in Boston
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.

Popular places to visit

Northeast Paddleboard Company

Take the family on an outing to Northeast Paddleboard Company during your trip to Boston. Amble around the area's riverfront or attend a sporting event.

Northeast Paddleboard Company

Frequently asked questions

How much does a Boston holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Boston costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Boston?
If you're hoping to snag a cheap Boston holiday package, consider travelling in January, February and March. You'll usually find better rates on flights and accommodation during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Boston?
With a well-organised schedule, you can easily tick off the top Boston attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, think about booking your Boston holiday for longer.
How to find the best Boston package deals?
Bagging a cheap Boston package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Boston package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Boston holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights individually. Better still, you can personalise your Boston getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Boston?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Boston holiday.
How to plan a trip to Boston?

  1. Pick your dates: What you plan to do in Boston and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Boston. Then, pick a hotel that suits your budget, whether that's an economical stay or a swankier retreat.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Boston. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Boston holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.