New Windsor Holidays

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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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    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in New Windsor

Hyatt Place Baltimore/Owings Mills
Hyatt Place Baltimore/Owings Mills
3 out of 5
4730 Painters Mill Rd, Owings Mills, MD
Fully refundableReserve now, pay when you stay
The price is S$144 per night from 25 Nov to 26 Nov
S$144
includes taxes & fees
25 Nov - 26 Nov
8/10 Very Good! (1,000 reviews)
"Good deal for the money. Even have a half decent breakfast. Only downside is this is an older facility with no usb ports in the rooms so bring an adapter."

Reviewed on 14 Nov,2024

Hyatt Place Baltimore/Owings Mills
Country Inn & Suites by Radisson, Frederick, MD
Country Inn & Suites by Radisson, Frederick, MD
3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is S$113 per night from 22 Dec to 23 Dec
S$113
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (1,004 reviews)
"Nice place and a value at the price point. Gracious staff and convenient location."

Reviewed on 21 Nov,2024

Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick
Hilton Garden Inn Frederick
3 out of 5
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is S$176 per night from 15 Dec to 16 Dec
S$176
includes taxes & fees
15 Dec - 16 Dec
8.8/10 Excellent! (1,000 reviews)
"Check-in was easy. The room was neat and clean. The surrounding area felt safe and secure."

Reviewed on 18 Nov,2024

Hilton Garden Inn Frederick
See all 280 properties in New Windsor
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 New Windsor holiday package cost?
Our New Windsor packages, which start from just , are the easiest way to save loads of cash. Pick and choose your favourite hotels, flights and rental car to create your ideal itinerary.
How do I get a cheap travel package to New Windsor?
Book everything all in one place with our New Windsor holiday packages. We have deals on flights, hotels, tours and more that’ll keep your credit card happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotels all over the world to pick from, you have countless opportunities to mix and match as you want.
How far in advance should I book my New Windsor holiday?
To land rock-bottom prices, book early. Airlines typically release tickets, along with some of the lowest fares, around a year in advance. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you’re in need of a last-minute getaway in New Windsor, there are always plenty of great bargains to be had on Expedia. Check them out now!
What does an Expedia New Windsor travel package include?
Travel packages include rental cars, hotels and flights, but you can mix and match them to create your ideal New Windsor holiday. You can also add on a few tours and activities once you’ve made your booking. You’re in control! When you bundle your bookings with Expedia, you’ll get access to discounts you won’t find elsewhere.
What should I know before booking a New Windsor travel package?
Bundling your bookings into a New Windsor holiday package is the most convenient way to organise your trip. Not only that, you’ll get great discounts just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on a tour or an activity?
Can I choose my airline with a New Windsor Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to pick from across the world. With so many choices, finding the right carrier to whisk you off to New Windsor will be a breeze.
If I'm not able to travel, can I cancel my New Windsor holiday package?
Whether it’s your hotel or flight, you can cancel or alter it. Booked your New Windsor holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We’re here to help you each step of the way.

* 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.