Greenwood Vacations from $326

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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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $554, price is now $326 per person
$326
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.

Reviewed on Oct 10, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,020, price is now $524 per person
$524
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $649, price is now $347 per person
$347
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast was incredible

Reviewed on Oct 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,182, price is now $1,274 per person
$1,274
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Everything was great

Reviewed on Oct 12, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $561, price is now $329 per person
$329
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
It felt very safe and was very clean. The stuff was all ver nice and helpful. The area was nice to walk on the pier but if wanting to do anything downtown it required a lot of uber using.

Reviewed on Oct 12, 2025

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Greenwood Hotel Deals

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
$142 nightly
The price is $157 total per night from Oct 16 to Oct 17
$157 total
Oct 16 - Oct 17
Total with taxes and fees
8.4/10 Very Good! (1,585 reviews)
"We loved the Abbey Resort! Probably our favorite place to stay at when we are in lake geneva. The vibes are so peaceful and beautiful. Must go to Coffee Mill for amazing coffee too!"

Reviewed on Oct 9, 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
$177 nightly
The price is $198 total per night from Oct 20 to Oct 21
$198 total
Oct 20 - Oct 21
Total with taxes and fees
8.6/10 Excellent! (3,007 reviews)
"Clean, everyone was friendly and happy to help. Waterpark was well staffed, clean and safe. Food was good we had the pizza. Arcade was fun and parking was easy. Rooms were clean and well kept and showed had great pressure. Overall a good experience"

Reviewed on Oct 11, 2025

Timber Ridge Lodge and Waterpark
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
$138 nightly
The price is $157 total per night from Oct 14 to Oct 15
$157 total
Oct 14 - Oct 15
Total with taxes and fees
9/10 Wonderful! (1,303 reviews)
"Great location , walking dostanie to Lake and restaurants. The outside is dated but the rooms are new and surprisingly well equipped."

Reviewed on Oct 13, 2025

Harbor Shores on Lake Geneva
See all 1,044 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.

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 $326 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.