Westchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Westchester Vacation
Save time and energy on your travel planning with a Westchester vacation package. One of the best neighborhoods to base yourself in this amazing city is Wellington, which is good for culture and much more. You'll want to sightsee during your trip to Westchester. Don't miss major attractions such as Historic Manassas Visitor Center, Hylton Performing Arts Center and Manassas Museum. Don't delay exploring this destination any longer. Your dream Westchester vacation is only a few clicks away with Expedia.
Ready to book your vacation to Westchester?
Westchester Hotel Deals
Courtyard by Marriott Springfield
6710 Commerce St Springfield VA
Fully refundableReserve now, pay when you stay
CA $168
CA $194 total
Oct 8 - Oct 9
includes taxes & fees
Hyatt Place Herndon Dulles Airport East
13711 Sayward Blvd Herndon VA
Fully refundableReserve now, pay when you stay
CA $144
CA $166 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very good! (3,184 reviews)
"My stay was wonderful, staff was great"
Reviewed on Oct 5, 2026
Best Western Fairfax
3535 Chain Bridge Rd Fairfax VA
Fully refundableReserve now, pay when you stay
CA $129
CA $154 total
Oct 30 - Oct 31
includes taxes & fees
8.2/10 Very good! (1,712 reviews)
"We saw several roaches in the bathroom and when we opened the drawer between the beds… also noticed a significant amount of mold on the curtains. Other than that the cleanliness was generally good. The room got hot though and the air conditioning didn’t seem to properly cool the room down. Breakfast ..."
Reviewed on Oct 5, 2026
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
Sushi Masterclass in Washington D.C. (Includes 4-Course Meal)
CA $175
per adult
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 — perfect for budget-conscious travellers.
How many days is enough for Westchester?
With around 2 days, you'll have enough time to visit popular neighbourhoods such as Manassas Park and Loch Lomond during your Westchester vacation. Remember to also add Hylton Performing Arts Centre and Old Dominion Speedway to your list of must-sees. In the mood for more adventures? Consider exploring outside of Westchester on tours and day trips.
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?
- Choose your travel dates: The things you want to do in Westchester and your favourite season can help you decide when to get away.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
