Westchester Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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    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

Find the Best Westchester Vacation Packages

Westchester Hotel Deals

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 AEDĀ 453 per night from Jul 24 to Jul 25
AEDĀ 453
AEDĀ 521 total
24 Jul - 25 Jul
includes taxes & fees
8.8/10 Excellent! (1,847 reviews)
"I recently stayed at the Hyatt Regency Dulles internationalAirport hotel and had a wonderful experience. The check-in process was smooth, the rooms were clean and comfortable, and the staff was incredibly helpful. I would highly recommend this hotel to anyone traveling through the area."

Reviewed on 20 July 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 AEDĀ 379 per night from Jul 26 to Jul 27
AEDĀ 379
AEDĀ 436 total
26 Jul - 27 Jul
includes taxes & fees
Courtyard by Marriott Springfield
Hilton Fairfax

Hilton Fairfax

3.5 out of 5
12777 Fair Lakes Cir Fairfax VA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 449 per night from Aug 7 to Aug 8
AEDĀ 449
AEDĀ 516 total
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (1,101 reviews)
"Large rooms; strong shower; comfortable beds; lots of pillows; nice towels; bathrooms/rooms are old style/dated appearance. Coffee not available in lounge until AFTER restaurant/Starbucks counter are opened at 6:30. The Expedia add tempted you with rooms for ~142$; but in reality the cost was over ..."

Reviewed on 21 July 2026

Hilton Fairfax
See all 729 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.

Frequently asked questions

How much does a Westchester vacation package cost?
You'll find cheap prices on Expedia for your Westchester getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Westchester costs.
What are the cheapest months to go to Westchester?
If you're looking to score a cheap Westchester vacation package, consider planning a trip in January, February and November. You'll usually find lower rates on flights and accommodations during these quieter months ā€” perfect for budget-conscious travelers.
How to find the best Westchester package deals?
Use Expedia's handy filters to help you find some terrific Westchester package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Westchester package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Westchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Westchester getaway to fit your exact style. Choose 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 vacation package to Westchester?
If you're considering an impromptu Westchester vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Westchester?

  1. Choose your travel dates: The things you want to do in Westchester and your favorite season can help you decide when to get away.
  2. Budget wisely: As well as the price of your hotel, you should consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Westchester.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Westchester. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Westchester vacation package that brings all your bookings together.