Greenwood Vacations from $319

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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.
HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,003 reviews)
Wasn’t as nice as I thought it would be. Very plain. Needs a lot of updating. It is clean though.

Reviewed on Jun 6, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Bathroom tile was loose and shower grout sisnr look to clean.

Reviewed on Jul 13, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
per person
Aug 28 - Sep 2
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (126 reviews)
The views are great in this historic Inn. Layed back but still classy. Away from the crowds but great dining that adds some fun. Could use a few room convinces and amenities like a working coffee and micro.

Reviewed on Jun 29, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

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Greenwood Hotel Deals

Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $208 total per night from Jul 14 to Jul 15
$208 total
Jul 14 - Jul 15
Total includes taxes and fees
9/10 Wonderful! (1,200 reviews)
"everything was wonderful except mattresses. It filled like waterbed."

Reviewed on Jul 11, 2025

Harbor Shores on Lake Geneva
Abbey Resort and Avani Spa
Abbey Resort and Avani Spa
3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $150 total per night from Aug 11 to Aug 12
$150 total
Aug 11 - Aug 12
Total includes taxes and fees
8.4/10 Very Good! (1,396 reviews)
"Nice hotel in a beautiful location!"

Reviewed on Jul 12, 2025

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark
Timber Ridge Lodge and Waterpark
3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $293 total per night from Aug 10 to Aug 11
$293 total
Aug 10 - Aug 11
Total includes taxes and fees
8.6/10 Excellent! (2,890 reviews)
"We had a great time!"

Reviewed on Jul 10, 2025

Timber Ridge Lodge and Waterpark
See all 1,034 properties in Greenwood
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 $319 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.