Westchester 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 Westchester

Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 24 Jul to 25 Jul
S$183
24 Jul - 25 Jul
includes taxes & fees
8.8/10 Excellent! (1,845 reviews)
"Five star staff great Acomodations. After acstresful weekeend everthing from the best burger I’ve had in a while. Thank you"

Reviewed on 20 Jul, 2026

Hyatt Regency Dulles International Airport
Courtyard by Marriott Springfield

Courtyard by Marriott Springfield

3 out of 5
6710 Commerce St Springfield VA
Fully refundableReserve now, pay when you stay
The price is S$163 per night from 24 Jul to 25 Jul
S$163
24 Jul - 25 Jul
includes taxes & fees
Courtyard by Marriott Springfield
Wingate by Wyndham Springfield

Wingate by Wyndham Springfield

3 out of 5
6550 Loisdale Court Springfield VA
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 28 Jul to 29 Jul
S$145
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very good! (1,612 reviews)
"It was okay"

Reviewed on 19 Jul, 2026

Wingate by Wyndham Springfield
See all 723 properties in Westchester
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.

What to do in Westchester

Turkish Mosaic Lamp Workshop in Chantilly

Turkish Mosaic Lamp Workshop in Chantilly

S$128
per adult
Turkish Mosaic Lamp Workshop in Chantilly
Smithsonian Air and Space Museum, Udvar Hazy Center Tour

Transportation To/From Air and Space Museum, Udvar Hazy Center

S$711
per traveller
Transportation To/From Air and Space Museum, Udvar Hazy Center
Sushi Masterclass in Washington D.C.

Sushi Masterclass in Washington D.C. (Includes 4-Course Meal)

S$161
per adult
Sushi Masterclass in Washington D.C. (Includes 4-Course Meal)
See all activities in Westchester

Frequently asked questions

How much does a Westchester holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Westchester costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Westchester?
January, February and November are the best times to look for cheap Westchester holiday packages. Opting to travel in less busy periods means you can typically find lower prices on accommodation and flights.
How many days is enough for Westchester?
With a well-planned schedule, you can easily tick off the most popular Westchester sights in a few days. But if you want to venture off the beaten track or go on day trips, consider booking your Westchester holiday for longer.
How to find the best Westchester package deals?
Finding a cheap Westchester package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Westchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging accommodation and flights individually. Better still, you can personalise your Westchester getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Westchester?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Westchester getaway.
How to plan a trip to Westchester?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to holiday in Westchester.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Westchester. Then, pick a property that suits your budget, whether that's a low-cost stay or a more upscale getaway.
  3. Decide how long to go for: Now that you're up to speed on Westchester, you can work out the right length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Westchester holiday package for you.

* 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.