A cityscape with a marina filled with boats, high-rise buildings, and a river.

Maryland 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*
  • Find the right fit

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

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

Top Maryland flight & hotel packages

Price found within the past 48 hours. Click for updated prices.
  • 15 Dec - 22 Dec

    Ink 48 Hotel + Flight

    Manhattan
    6 nights
    4.5 star property
    8.4/10 - Very good (1,837 reviews)
    "The staff are the Superhero of this hotel. The hotel does need to be a little more clean & maybe a humidifier - the room was dry & carpet seems dirty. However amazing location & the staff is A+"
    Reviewed November 9, 2026
    Return • Singapore (SIN) - New York (JFK)
    SIN - JFK • 1 stop JFK - SIN • 1 stop
    S$4,658
    S$3,506
    per traveller
    found 0 hours ago
    Ink 48 Hotel
  • 15 Dec - 22 Dec

    The St. Regis New York + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Return • Singapore (SIN) - New York (JFK)
    SIN - JFK • 1 stop JFK - SIN • 1 stop
    Save 100% on your flight
    S$14,895
    S$10,952
    per traveller
    found 0 hours ago
    The St. Regis New York
  • 15 Dec - 22 Dec

    Margaritaville Resort Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (4,179 reviews)
    Return • Singapore (SIN) - New York (JFK)
    SIN - JFK • 1 stop JFK - SIN • 1 stop
    S$4,956
    S$3,728
    per traveller
    found 0 hours ago
    Margaritaville Resort Times Square
  • 15 Dec - 22 Dec

    33 Hotel, New York City, Seaport + Flight

    Manhattan
    6 nights
    5.0 star property
    9.0/10 - Wonderful (1,002 reviews)
    "The staff is amazing, especially Tommy and Chris. Super helpful and welcoming. Our room was spotless and beautiful in a city where things are not easily kept that way."
    Reviewed November 7, 2026
    Return • Singapore (SIN) - New York (JFK)
    SIN - JFK • 1 stop JFK - SIN • 1 stop
    S$4,715
    S$3,550
    per traveller
    found 0 hours ago
    33 Hotel, New York City, Seaport
  • 15 Dec - 22 Dec

    The Lombardy Hotel + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,621 reviews)
    "Great location,"
    Reviewed November 10, 2026
    Return • Singapore (SIN) - New York (JFK)
    SIN - JFK • 1 stop JFK - SIN • 1 stop
    S$6,423
    S$5,118
    per traveller
    found 0 hours ago
    The Lombardy Hotel

Maryland Hotel Deals

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.

Frequently Asked Questions

How much does a Maryland holiday package cost?

Offering great value package deals from S$3,506 on Expedia, you'll be pleasantly surprised at how much a holiday to Maryland costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Maryland?

Travel in the low or shoulder season and you're likely to score cheap Maryland holiday packages. Keep in mind that public holidays and local festivals and events can impact prices, so do a little research before booking.

How many days is enough for Maryland?

The ideal duration for your Maryland holiday depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to hit all the major sights and explore some hidden spots along the way.

How to find the best Maryland package deals?

Begin your search for a Maryland package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Maryland package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Maryland adventure underway.

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

You can enjoy significant savings on your Maryland break by booking a tailored holiday package. Check the "Package" heading, then enter your destination and travel dates to view some great flight and hotel prices. Bundle everything into a neat 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 Maryland?

If you have your Maryland travel dates locked in, book as soon as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.

How to plan a trip to Maryland?

  1. Choose when to get away: Check your schedule and get packing. Your favourite time of year and the activities available will also help you decide when to escape to Maryland.
  2. Plan your budget wisely: On top of the cost of your accommodation, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may come up during your trip to Maryland.
  3. Decide how long to go away for: Now that you're more familiar with Maryland, you can figure out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Maryland 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.