Greenwood Vacations from $404
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Your Greenwood Vacation
Take the guesswork out of travel planning with a Greenwood vacation package. A good neighborhood to stay in this captivating city is Powers Lake, which is good for watersports and a lot more. If taking in sights is on the agenda during your trip to Greenwood, visit top attractions like McHenry County Courthouse, Petersen Park Beach and Woodstock Opera House. Whatever your travel plans or budget, putting together the ultimate tailored Greenwood vacation is a piece of cake with Expedia.
The Latest Greenwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
$497
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!
Reviewed on Oct 17, 2026
Greenwood Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$130 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
$170 nightly
$190 total
Nov 10 - Nov 11
Total with taxes and fees
8.6/10 Excellent! (3,485 reviews)
"Nice experience definitely recommend it"
Reviewed on Oct 16, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
$131 nightly
$149 total
Nov 16 - Nov 17
Total with taxes and fees
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.
Find the Best Greenwood Vacation Packages
Greenwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Volo Auto Museum, McHenry Shores Beach Park and Petersen Park Beach |
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Frequently asked questions
How much does a Greenwood vacation package cost?
You'll find cheap prices from $404 on Expedia for your Greenwood escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Greenwood costs.
What are the cheapest months to go to Greenwood?
You can typically find lower rates and greater availability in January, October and November. Explore our cheap Greenwood vacation packages and you could get some great off-season deals.
How many days is enough for Greenwood?
Typically, a handful of days is enough to explore the major attractions during your Greenwood vacation. But if you prefer to have time to rest or go on day tours, think about extending your itinerary.
How to find the best Greenwood package deals?
Begin your search for a Greenwood package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Greenwood package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Greenwood escape underway.
Is it cheaper to book a Greenwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. 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 individually. And you'll still have the freedom to create a personalized Greenwood vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Greenwood?
If you're considering a spur-of-the-moment Greenwood getaway, 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 find amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
Your Greenwood trip is meant to be a relaxing escape from your busy life, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
