Westchester Holidays

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Top hotels in Westchester

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €118 per night from 24 Dec to 25 Dec
€118
includes taxes & fees
24 Dec - 25 Dec
7.8/10 Good! (8,279 reviews)
"This is a very old property which is part of it's charm. Water pressure in the shower was very limited. Accomodations are simple. Really liked new vinyl flooring in room with throw rug. Much better than carpeting. I will return."

Reviewed on 21 Dec 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €105 per night from 21 Jan to 22 Jan
€105
includes taxes & fees
21 Jan - 22 Jan 2025
8.6/10 Excellent! (3,626 reviews)
"Having to park my car 4 blocks away"

Reviewed on 22 Dec 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €194 per night from 5 Jan to 6 Jan
€194
includes taxes & fees
5 Jan - 6 Jan 2025
9/10 Wonderful! (3,125 reviews)
"We were upgraded to a room with a view of the river wh"

Reviewed on 22 Dec 2024

Hyatt Regency Chicago
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 holiday package cost?
You’ll find cheap prices on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Westchester costs.
What are the cheapest months to go to Westchester?
If you’re hoping to score a cheap Westchester holiday package, consider planning a trip in November, December and January. You’ll usually find lower prices on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Westchester?
The ideal duration for your Westchester holiday depends on what you’d like to do and see. Usually, a handful of days to a week will give you plenty of time to tick off all the main sights and explore some hidden spots along the way.
How to find the best Westchester package deals?
Bagging a cheap Westchester package deal is a cinch with Expedia. After you’ve entered your trip dates and destination under our “Packages” tab, set your budget range, add a few filters and browse what’s available. You can personalise your search by “Popular locations,” “Property type,” “Guest rating” and more. Sort the results by “Price: low to high” to view the most economical Westchester package deals. Want a simple trick to score the biggest savings? Be flexible 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?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You’ll typically snag a better deal than booking each component separately. And you’ll still enjoy the freedom to create a personalised Westchester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Westchester?
Land incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Westchester escape.
How to plan a trip to Westchester?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Westchester.
  2. Set your budget: Factor in expenses like flights, transportation and food when calculating how much to put aside for your trip to Westchester. Then, select a property that works with your budget, whether that’s a wallet-friendly stay or a high-end retreat.
  3. Decide how long to go away for: Now that you’re more familiar with Westchester, you can work out the right length of your break. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your accommodation and airfare: After you’ve nailed down your trip dates and duration, book the ideal Westchester holiday package for you.

Popular places to visit

What to do in Westchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.