Name: Timber Ridge Lodge and Waterpark
Price range: CA $198
Rating: 8.6

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.

Top Greenwood Vacation Deals

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

Level Chicago – Old Town

Downtown Chicago

CA $1,082

per person

Jul 9 - Jul 12

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (463 reviews)

Eric and the rest of the staff was very helpful from check in to check out! The place is very lovely!!!!! Would come back again soon!

Reviewed on Apr 23, 2026

Swissotel - Chicago

Downtown Chicago

CA $1,722

per person

Jun 4 - Jun 8

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (3,280 reviews)

Really good spot and location. Staff was super helpful and nice.

Reviewed on Apr 22, 2026

The Wade

Downtown Chicago

CA $1,421

per person

Jun 3 - Jun 8

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

8.4/10 Very Good! (1,804 reviews)

Wonderful place to stay in Chicago. Perfect location right by Navy Pier, amazing view from the window, clean rooms, comfortable beds, friendly staff, great food options.

Reviewed on Apr 23, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,387

per person

Jun 9 - Jun 14

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (455 reviews)

Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on Apr 23, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $3,155

per person

Jun 5 - Jun 12

just found

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,848 reviews)

Great staff, facilities, esp the fitness & spa

Reviewed on Apr 23, 2026

Ready to book your vacation to Greenwood?

Choose your dates

Greenwood Hotel Deals

Abbey Resort and Avani Spa

269 Fontana Boulevard Fontana WI

Fully refundableReserve now, pay when you stay

CA $125

CA $174 total

Apr 27 - Apr 28

includes taxes & fees

8.6/10 Excellent! (1,852 reviews)

The pool had a very strong chlorine smell. So bad we didn’t get to enjoy it for a long time since it hurt our eyes.

Reviewed on Apr 23, 2026

The Cove Of Lake Geneva

111 Center St Lake Geneva WI

9/10 Wonderful! (1,454 reviews)

Very welcoming atmosphere, the room was comfortable, front desk staff were very friendly.

Reviewed on Apr 21, 2026

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Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Fully refundableReserve now, pay when you stay

CA $198

CA $274 total

May 12 - May 13

includes taxes & fees

8.6/10 Excellent! (3,234 reviews)

The establishment was nice and the room was nice but some of the staff were not very helpful and I felt they were being unexplainable rude to my family and guests making up rules for us specially.

Reviewed on Apr 21, 2026

See all 1,033 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.