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Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Greenwood holiday rentals

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is AU$358
includes taxes & fees
7 Oct - 8 Oct
The Tailor House
Living area

2. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat
Wonder Lake
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is AU$587
includes taxes & fees
5 Oct - 6 Oct
Wonder Lake Elegance: Serene 2BR Townhome Retreat
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

3. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.6 out of 10, Excellent, (12 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is AU$421
includes taxes & fees
4 Oct - 5 Oct
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

4. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (17 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is AU$420
includes taxes & fees
20 Oct - 21 Oct
Richmond No. 267 Boutique Loft Apartment
An aerial view of a marina with multiple docks and boats, a sandy beach, and surrounding greenery.

5. The Little Farm Fontana 5 min from Geneva Lake!

The Little Farm Fontana 5 min from Geneva Lake!
Fontana-on-Geneva Lake
10.0 out of 10, Exceptional, (1 review)
"Cute little place in a convenient location for a fair price."
United States
Linda C.
The price is AU$325
includes taxes & fees
4 Oct - 5 Oct
The Little Farm Fontana 5 min from Geneva Lake!
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

6. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,462 reviews)
"I love this place"
United States
Edgar
The price is AU$216
includes taxes & fees
20 Oct - 21 Oct
Timber Ridge Lodge and Waterpark
A modern living room with a green sofa, a white coffee table, and a ceiling fan.

7. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
Lake Geneva
9.2 out of 10, Wonderful, (29 reviews)
"Loved the couches! Quick walk to wonderful restaurants and lake."
United States
Denise A.
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

8. Sanctuary Woodland Guest House, located next to the conservation area!

Sanctuary Woodland Guest House, located next to the conservation area!
Harvard
10.0 out of 10, Exceptional, (28 reviews)
"The property is so cute and it was the perfect, quiet place to stay! The owner was super friendly as well!"
United States
Jamie S.
The price is AU$290
includes taxes & fees
25 Oct - 26 Oct
Sanctuary Woodland Guest House, located next to the conservation area!
A cozy living room with a wooden dining table, a blue sofa with colorful cushions, a large window with curtains, and a potted plant.

9. Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking

Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking
Lake Geneva
10.0 out of 10, Exceptional, (11 reviews)
"Host was very communicative and friendly and helpful. Location and rooms were excellent. "
United States
Michael B.
The price is AU$324
includes taxes & fees
5 Oct - 6 Oct
Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking
A beach with a lifeguard tower, a building with a sign reading 'Boat Tours & Charter,' and a sandy shore with people and beach equipment.

10. Cozy Lake Geneva, King Bed, Fireplace & Pool

Cozy Lake Geneva, King Bed, Fireplace & Pool
Lake Geneva
10.0 out of 10, Exceptional, (45 reviews)
"Our host Nicole was awesome! Great communication and the property was excellent. We loved the location!"
United States
Zachary B.
The price is AU$438
includes taxes & fees
4 Oct - 5 Oct
Cozy Lake Geneva, King Bed, Fireplace & Pool
A swimming pool with a 5ft depth marker, surrounded by lounge chairs and a stone wall.

11. LG 1+1 Condo on Lakeshore - pool - walk to Lake

LG 1+1 Condo on Lakeshore - pool - walk to Lake
Lake Geneva
The price is AU$723
includes taxes & fees
14 Oct - 15 Oct
LG 1+1 Condo on Lakeshore - pool - walk to Lake
A two-story house with a front porch, a mailbox, and a number '10216' on the door.

12. 1905 Victorian Farmhouse close to Lake Geneva.

1905 Victorian Farmhouse close to Lake Geneva.
Hebron
10.0 out of 10, Exceptional, (32 reviews)
"Repeat guest! We will be looking for this property again if we stay in the same area."
United States
Shari
The price is AU$1,492
includes taxes & fees
4 Oct - 5 Oct
1905 Victorian Farmhouse close to Lake Geneva.
A building with a sign reading "Angels Home & Garden" and a sign for "Geneva Lakes Vacations".

13. Second Level Elevated Escape |The Crows Nest | 1.9 miles to Fontana and Abbey Resort

Second Level Elevated Escape |The Crows Nest | 1.9 miles to Fontana and Abbey Resort
Walworth
10.0 out of 10, Exceptional, (59 reviews)
"Very large property located in a great spot for walworth/lake Geneva access. Very modern home with lots of space"
Canada
Olivia
The price is AU$550
includes taxes & fees
4 Oct - 5 Oct
Second Level Elevated Escape |The Crows Nest | 1.9 miles to Fontana and Abbey Resort
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

14. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
9.4 out of 10, Exceptional, (3 reviews)
"Nice quiet spot to rest a Travelers head"
United States
Dan K.
The price is AU$424
includes taxes & fees
12 Oct - 13 Oct
Spacious 3 Bedroom
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

15. Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6

Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
Lake Geneva
9.0 out of 10, Wonderful, (19 reviews)
"Super clean,quiet house! Close to water for us to launch our boat. We would definitely stay again, Thank You"
United States
kelly b.
The price is AU$357
includes taxes & fees
20 Oct - 21 Oct
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
Wicker furniture with cushions, a small table with a pineapple, and a glass enclosure with logs.

16. Geneva Beach House Como Suite Walk to Lake Shore Path Near Downtown

Geneva Beach House Como Suite Walk to Lake Shore Path Near Downtown
Lake Geneva
9.8 out of 10, Exceptional, (20 reviews)
"Property was cozy and had great access to all areas of Lake Geneva."
United States
Paul
The price is AU$385
includes taxes & fees
6 Oct - 7 Oct
Geneva Beach House Como Suite Walk to Lake Shore Path Near Downtown
A modern kitchen with green cabinets, a dining area with a table and chairs, and a view of the outside through a window with a curtain.

17. Broad Street Suite 3|Parking for 3 Vehicles |Walkable |Boho Inspired |Full Kitchen |Huge Living Room

Broad Street Suite 3|Parking for 3 Vehicles |Walkable |Boho Inspired |Full Kitchen |Huge Living Room
Lake Geneva
9.6 out of 10, Exceptional, (15 reviews)
"It was a great experience to stay here!"
United States
Jacqueline
Broad Street Suite 3|Parking for 3 Vehicles |Walkable |Boho Inspired |Full Kitchen |Huge Living Room
An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

18. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,264 reviews)
"Super friendly staff, perfect hotel for romantic gateway."
United States
Daniel
The price is AU$351
includes taxes & fees
12 Oct - 13 Oct
Mill Creek Hotel
A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

19. Quaint, quiet condo minutes from Lake Geneva

Quaint, quiet condo minutes from Lake Geneva
Lake Geneva
9.6 out of 10, Exceptional, (40 reviews)
"Nice reasonable price"
United States
Angela
The price is AU$511
includes taxes & fees
1 Oct - 2 Oct
Quaint, quiet condo minutes from Lake Geneva
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

20. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is AU$734
includes taxes & fees
5 Oct - 6 Oct
King bed Crystal Lake Mchenry Cary Cozy
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

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

10/10 Excellent
"Overall a great experience. Cleanliness is lacking, and the rooms are extremely outdated for 2026. Nice and spacious at least, and the water park area is very neat. Lifeguards should do a better job of making sure all of the excessively empty tubes are out of the lazy river when they aren’t being used though. Kinda irritating floating with the family and constantly running into empty inner tubes. I started to clear some out and the lifeguard blew her whistle at me and said I couldn’t do that. If that’s the case, make sure the extra lifeguards are clearing the water of all the extra inner tubes that are empty. Good experience overall!"
Anthony 2-night trip
Posted 2 hours ago
Timber Ridge Lodge and Waterpark

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$216 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?

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Greenwood?

While exploring the area, visit family-friendly sights like Illinois Railway Museum, or get outside and enjoy nature at McCullom Lake. In the wider area, you’ll find Petersen Park Beach and McHenry County Fairgrounds.

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.