Westchester 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 Westchester

Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is S$186 per night from 26 Jul to 27 Jul
S$186
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (1,365 reviews)
"Hotel was under major internal constructio. Gym, pool and hot tub were not available."

Reviewed on 21 Jul, 2025

Hyatt Regency Dulles
Best Western Fairfax

Best Western Fairfax

2.5 out of 5
3535 Chain Bridge Rd, Fairfax, VA
Fully refundableReserve now, pay when you stay
The price is S$126 per night from 15 Aug to 16 Aug
S$126
15 Aug - 16 Aug
includes taxes & fees
8/10 Very Good! (1,143 reviews)
"The room was clean. The pool area looked nice, but the hours were limited, so we never got to use it. Parking outside our room was close and convenient."

Reviewed on 23 Jul, 2025

Best Western Fairfax
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
The price is S$157 per night from 3 Aug to 4 Aug
S$157
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (2,315 reviews)
"Sheets were sketchy…swapped out for the spare set. Overall good experience"

Reviewed on 21 Jul, 2025

Hyatt Place Herndon Dulles Airport East
See all 633 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.

Popular places to visit

Manassas Museum

You can spend time exploring the galleries in Manassas Museum in Manassas. Experience the lively festivals and fascinating museums in this family-friendly area.

Manassas Museum

What to do in Westchester

Battles of Bull Run Private Battlefield Tour

Battles of Bull Run Private Battlefield Tour

S$383
per traveller
Battles of Bull Run Private Battlefield Tour
Smithsonian Air and Space Museum, Udvar Hazy Center Tour

Smithsonian Air and Space Museum, Udvar Hazy Center Tour

S$704
per traveller
Smithsonian Air and Space Museum, Udvar Hazy Center Tour
Sushi Masterclass in Washington D.C.

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

S$152
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.