Greenwood Holidays

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Top Flight + Hotel Deals in Greenwood

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
The hotel overall was great.

Reviewed on 7 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on 7 Jul 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Hotel is on a prime location which was nice. House keeping was on point. Honestly is overpriced for what you get (not even free breakfast ) we had to drive around twice to figure out where the lobby was, went inside to find out where to park or check in did not find anybody to assist us. Air conditioning worked whenever it pleased, can barely see the numbers on the displayed monitor.. Only good thing was location.

Reviewed on 6 Jul 2025

The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
There are a lot of dining options in the Hoxton and nearby ie the Fulton Market, which made it convenient for meals. The Hoxton also seemed to be very popular for meetings and relaxed get togethers which added to the vibrancy of the hotel.

Reviewed on 6 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
21 Aug - 25 Aug
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Great stay. Elevators were a lot slow but overall great property and great service!

Reviewed on 6 Jul 2025

Top hotels in Greenwood

Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
The price is €164 per night from 9 Jul to 10 Jul
€164
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (1,186 reviews)
"Great location and view"

Reviewed on 7 Jul 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
The price is €125 per night from 6 Aug to 7 Aug
€125
6 Aug - 7 Aug
includes taxes & fees
8.4/10 Very Good! (1,372 reviews)
Everything perfect but the front desk!
"Your not so nice desk clerk has twice now not been too welcoming. She doesnt wear a name tag, was the blonde at 1:48 pm on 7/1. Telling us we needed to pay an early check-in fee before 2pm, stating our room WAS ready. When i showed her the time on my phone, she then stated it was NOT ready. Stares ..."

Reviewed on 3 Jul 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
The price is €227 per night from 4 Aug to 5 Aug
€227
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (2,881 reviews)
"Great water park, water is warmer which we enjoyed. My toddler loves water and had a blast. Water park is clean lots of lifeguards. The 2 bedroom suite we got was ok. We noticed at night that the top room was hot and unable to cool it with the lower room AC. The ceiling fan didn’t do much to help ..."

Reviewed on 6 Jul 2025

Timber Ridge Lodge and Waterpark
See all 1,035 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.

Frequently asked questions

How much does a Greenwood holiday package cost?
You'll find cheap prices from €853 on Expedia for your Greenwood escape. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Greenwood costs.
What are the cheapest months to go to Greenwood?
January, February and March are great times to search for cheap Greenwood holiday packages. Choosing to travel in quieter periods means you can typically find lower prices on flights and accommodation.
How many days is enough for Greenwood?
The ideal length of your Greenwood holiday depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to go to all the top sights and explore some hidden treasures along the way.
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 holiday as a package?
Expedia holiday 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 personalised Greenwood holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Greenwood?

  1. Choose your dates: What you want to do in Greenwood and your favourite season can help you decide when to get away.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Greenwood. Then, select a property that suits your budget, whether that's a low-cost option or a swankier retreat.
  3. Determine how many days away: Start by making a list of all the activities and sights you'd like to experience in Greenwood. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customised Greenwood holiday package.

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