New Windsor Holidays

  • 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 hotels in New Windsor

Sunday Morning at Savannahs

Sunday Morning at Savannahs

4 out of 5
111 South Springdale Avenue, New Windsor New Windsor MD
The price is S$256 per night from 15 Nov to 16 Nov
S$256
15 Nov - 16 Nov
includes taxes & fees
10/10 Exceptional! (2 reviews)
"We had a girls night here. Everything was excellent. It was a beautiful facility. It has lots of charming character. You feel like you have simply left home and went to stay at your grandmother's house, which is a very good thing In my book I felt right at home. When we arrived there were snacks ..."

Reviewed on 26 Oct, 2026

Sunday Morning at Savannahs
Turf Valley Resort

Turf Valley Resort

3.5 out of 5
2700 Turf Valley Rd Ellicott City MD
Fully refundableReserve now, pay when you stay
The price is S$208 per night from 16 Nov to 17 Nov
S$208
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"We have stayed at Turf Valley Resort the past 3 years when we do an annual visit to relatives in the area. It truly is an exceptional stay. Everything about the resort is first class. The rooms are clean, well furnished, comfortable and quiet. We look forward to returning again next year."

Reviewed on 11 Nov, 2026

Turf Valley Resort
Best Western Historic Frederick

Best Western Historic Frederick

2.5 out of 5
420 Prospect Blvd Frederick MD
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 20 Nov to 21 Nov
S$115
20 Nov - 21 Nov
includes taxes & fees
Best Western Historic Frederick
See all 339 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.

Stay near popular New Windsor attractions

Old Westminster Winery

6.8/10 (11 reviews)
You can enjoy a tasting or tour at Old Westminster Winery during your travels to New Windsor. While in this family-friendly area, you can enjoy the restaurants.
See properties

Frequently asked questions

How much does a New Windsor holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to New Windsor costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to New Windsor?
If you'd like to snag a cheap New Windsor holiday package, consider visiting in January, February and April. You'll usually find better rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for New Windsor?
Usually, a handful of days is enough to check out the major attractions during your New Windsor holiday. However, if you'd like to have some time to chill out or go on day trips, think about extending your itinerary.
How to find the best New Windsor package deals?
Begin your search for a New Windsor package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect New Windsor package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your New Windsor adventure off to a flying start.
Is it cheaper to book a New Windsor holiday as a package?
You can enjoy significant savings on your New Windsor retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your destination and travel dates to browse some great 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 New Windsor?
Enjoy fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment New Windsor trip.
How to plan a trip to New Windsor?

  1. Choose your dates: The things you want to do in New Windsor and your preferred season will help you decide when to get away.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to New Windsor. Then, choose a hotel that fits your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide how many days away: Start by making a list of all the activities and attractions you want to experience in New Windsor. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a New Windsor 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.