Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

Aparthotel in Lake Geneva

Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (3090)
"The property was very nice and the customer service was excellent."
United States
Ronda
The price is AU$271
includes taxes & fees
11 Jan - 12 Jan 2026
Timber Ridge Lodge and Waterpark

Aparthotel in Lake Geneva

Mill Creek Hotel
2.5 star property
9.2 out of 10, Wonderful, (1220)
"Enjoyed our stay, perfect location !"
United States
Lisa
The price is AU$274
includes taxes & fees
4 Jan - 5 Jan 2026
Mill Creek Hotel
10.0 out of 10, Exceptional, (10)
"Excellent property and location!"
United States
Rod L.
The price is AU$329
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
9.8 out of 10, Exceptional, (29)
"The location was easy to find and perfect walking distance to downtown. "
United States
Griffin Y.
The price is AU$544
includes taxes & fees
4 Jan - 5 Jan 2026
Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
9.8 out of 10, Exceptional, (61)
"Great location can walk to everything in downtown Lake Geneva. Well supplied with sheets, towels and toiletries. Nice place to stay"
United States
Laurie B.
The price is AU$567
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Downtown Lake Geneva Bungalow Walk to Beach Dining Nightlife
9.8 out of 10, Exceptional, (13)
"Great experience! Great Place!"
United States
Magda P.
The price is AU$529
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Lake Geneva Hideaway Balcony Walk to Beach Live Music Sleeps 8
9.6 out of 10, Exceptional, (13)
"The property was very nice! It was a relaxing stay and within walking distance to everything! "
United States
Barbara T.
The price is AU$501
includes taxes & fees
4 Jan - 5 Jan 2026
Broad Street Suite 3|Parking for 3 Vehicles |Walkable |Boho Inspired |Full Kitchen |Huge Living Room
9.6 out of 10, Exceptional, (12)
"Place was great, close to everything, and the little extras were a perfect touch."
United States
Linda
The price is AU$399
includes taxes & fees
4 Jan - 5 Jan 2026
Broad Street Suite 1 |Parking Available |Downton |Walkable |Above Restaurant | King & Queen Bedroom

Condo in Lake Geneva

Hidden Gem with Pool View!
10.0 out of 10, Exceptional, (38)
"Property was perfect. We were attending a wedding at the Getaway next door. Was nice to be able to just walk there."
United States
Susan F.
The price is AU$402
includes taxes & fees
4 Jan - 5 Jan 2026
Hidden Gem with Pool View!
9.8 out of 10, Exceptional, (11)
"Great place very clean"
United States
Heidi
The price is AU$529
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Lake Geneva New York Suite Walk to Beach Dining Shops Sleeps 8
The price is AU$972
includes taxes & fees
4 Jan - 5 Jan 2026
Salem Vacation Home w/ Dock: Steps to Paddock Lake
10.0 out of 10, Exceptional, (19)
"Property was cozy and had great access to all areas of Lake Geneva."
United States
Paul
The price is AU$358
includes taxes & fees
4 Jan - 5 Jan 2026
Geneva Beach House Como Suite Walk to Lake Shore Path Near Downtown
9.4 out of 10, Exceptional, (25)
"Location terrific to everything, had everything we needed and we were very comfortable. "
United States
Keith
The price is AU$425
includes taxes & fees
4 Jan - 5 Jan 2026
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
9.8 out of 10, Exceptional, (19)
"This place is in a perfect location to everything. We didn’t have to drive anywhere. Very clean and immediate response from owners about questions we had. Would definitely stay there again!"
United States
Jodie F.
The price is AU$934
includes taxes & fees
6 Jan - 7 Jan 2026
Downtown Lake Geneva Hideaway Walk to Lake Music Dining Balcony Sleeps 16
9.6 out of 10, Exceptional, (19)
"Great downtown location!"
United States
Illinois G.
The price is AU$476
includes taxes & fees
5 Jan - 6 Jan 2026
Suite 725 on Main |Recently Face-Lifted |Walkable Dwntwn Condo |Parking |Dining |Nightlife |Shopping
10.0 out of 10, Exceptional, (20)
"Great place. "
United States
Therese N.
The price is AU$546
includes taxes & fees
5 Jan - 6 Jan 2026
Relaxing Getaway/StepsToLake/Pool/Tennis near DT Lake Geneva
9.8 out of 10, Exceptional, (96)
"Fantastic location, space, and view. Would definitely stay again."
United States
Mary D.
The price is AU$617
includes taxes & fees
5 Jan - 6 Jan 2026
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
9.0 out of 10, Wonderful, (71)
"Loved the location and accessibility to so many things. Everything we needed was there. Thank you"
United States
Jane Burden B.
The price is AU$559
includes taxes & fees
5 Jan - 6 Jan 2026
Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake
10.0 out of 10, Exceptional, (5)
"Great location walking distance to downtown. Very cozy and clean property! "
United States
Amanda K.
The price is AU$879
includes taxes & fees
4 Jan - 5 Jan 2026
Broad Street Suites 2 & 3 | Parking for 5 Vehicles |Downtown|Walkable |1 Block to Horticultural Hall

Apartment in Fox Lake

Randolph Hotel Capone Suite 201
6.0 out of 10, (2)
"Staying in the Round Lake Beach area to visiting family. Room is great and clean. Pretty view of Fox Lake. Only draw back is it is over a bar. Karaoke comes right up through the floor. Not to much of a problem as the bar closes at 11:00. So just have to suffer through the drunken super star want a be singers. It is good for some laughs. Over all I would recommend this place in a heartbeat. "
United States
Daniel H.
The price is AU$762
includes taxes & fees
1 Jan - 2 Jan 2026
Randolph Hotel Capone Suite 201
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.
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Top Greenwood Hotel Reviews

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$271 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Greenwood has to offer?

Private Country House near Lake Geneva, Como and Williams Bay: This holiday home rental outside of Greenwood is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Greenwood?

While exploring the area, visit family-friendly sights like Jet Funn, or get outside and enjoy nature at Petersen Park Beach. In the wider area, you’ll find McHenry County Fairgrounds and Woodstock Square.

What are holiday rentals like in Greenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenwood. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for small groups.