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Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is CA $191
CA $368 total
includes taxes & fees
Sep 13 - Sep 14
The Tailor House

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 CA $282
CA $531 total
includes taxes & fees
Sep 14 - Sep 15
Wonder Lake Elegance: Serene 2BR Townhome Retreat

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
8.4 out of 10, Very good, (11 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is CA $237
CA $409 total
includes taxes & fees
Sep 7 - Sep 8
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

4. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,421 reviews)
"Fun place!"
United States
Dina
The price is CA $181
CA $255 total
includes taxes & fees
Oct 7 - Oct 8
Timber Ridge Lodge and Waterpark

5. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,257 reviews)
"Worked perfectly for my son, grandson and I. Unfortunately we didn’t get to have the breakfast because we were fishing very early each day. Loved the location, close to restaurants and the lake."
United States
Barbara
The price is CA $300
CA $341 total
includes taxes & fees
Oct 1 - Oct 2
Mill Creek Hotel

6. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (16 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is CA $239
CA $404 total
includes taxes & fees
Sep 28 - Sep 29
Richmond No. 267 Boutique Loft Apartment

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, (28 reviews)
"Loved the couches! Quick walk to wonderful restaurants and lake."
United States
Denise A.
The price is CA $96
CA $407 total
includes taxes & fees
Sep 13 - Sep 14
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

8. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is CA $156
CA $260 total
includes taxes & fees
Sep 8 - Sep 9
Little Fox Cottage - A Cozy Riverview Getaway

9. 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, (26 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 CA $180
CA $264 total
includes taxes & fees
Sep 8 - Sep 9
Sanctuary Woodland Guest House, located next to the conservation area!

10. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
The price is CA $217
CA $1,112 total
includes taxes & fees
Sep 13 - Sep 14
Modern Lake Geneva Condo With Views

11. Spacious 27’ RV on horse farm

Spacious 27’ RV on horse farm
Bristol
8.8 out of 10, Excellent, (10 reviews)
"It was perfect for my husband, myself and my daughter during the 4th of July weekend! "
United States
Faith N.
The price is CA $125
CA $161 total
includes taxes & fees
Sep 8 - Sep 9
Spacious 27’ RV on horse farm

12. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is CA $236
CA $683 total
includes taxes & fees
Sep 8 - Sep 9
King bed Crystal Lake Mchenry Cary Cozy

13. 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, (10 reviews)
"Host was very communicative and friendly and helpful. Location and rooms were excellent. "
United States
Michael B.
The price is CA $95
CA $331 total
includes taxes & fees
Sep 15 - Sep 16
Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking

14. 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 CA $197
CA $698 total
includes taxes & fees
Oct 5 - Oct 6
LG 1+1 Condo on Lakeshore - pool - walk to Lake

15. 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 CA $178
CA $346 total
includes taxes & fees
Sep 8 - Sep 9
The Little Farm Fontana 5 min from Geneva Lake!

16. Relaxing Getaway/StepsToLake/Pool/Tennis near DT Lake Geneva

Relaxing Getaway/StepsToLake/Pool/Tennis near DT Lake Geneva
Lake Geneva
10.0 out of 10, Exceptional, (24 reviews)
"Great place. "
United States
Therese N.
The price is CA $169
CA $533 total
includes taxes & fees
Sep 9 - Sep 10
Relaxing Getaway/StepsToLake/Pool/Tennis near DT Lake Geneva

17. Broad Street Suite 1 |Parking Available |Downton |Walkable |Above Restaurant | King & Queen Bedroom

Broad Street Suite 1 |Parking Available |Downton |Walkable |Above Restaurant | King & Queen Bedroom
Lake Geneva
9.4 out of 10, Exceptional, (16 reviews)
"Overall fantastic stay with the place, location, and accommodations!"
United States
Sydney B.
The price is CA $95
CA $386 total
includes taxes & fees
Sep 8 - Sep 9
Broad Street Suite 1 |Parking Available |Downton |Walkable |Above Restaurant | King & Queen Bedroom

18. Geneva Beach House Geneva Suite Walk to Lake Shore Path Sleeps 6 Parking

Geneva Beach House Geneva Suite Walk to Lake Shore Path Sleeps 6 Parking
Lake Geneva
9.8 out of 10, Exceptional, (19 reviews)
"We really enjoyed our stay and would definitely be come again"
United States
Sarah O.
The price is CA $107
CA $395 total
includes taxes & fees
Sep 13 - Sep 14
Geneva Beach House Geneva Suite Walk to Lake Shore Path Sleeps 6 Parking

19. Suite 725 on Main |Recently Face-Lifted |Walkable Dwntwn Condo |Parking |Dining |Nightlife |Shopping

Suite 725 on Main |Recently Face-Lifted |Walkable Dwntwn Condo |Parking |Dining |Nightlife |Shopping
Lake Geneva
9.8 out of 10, Exceptional, (22 reviews)
"Great location, right in middle if downtown, everything was walkable. "
United States
Jenny B.
The price is CA $152
CA $505 total
includes taxes & fees
Sep 9 - Sep 10
Suite 725 on Main |Recently Face-Lifted |Walkable Dwntwn Condo |Parking |Dining |Nightlife |Shopping

20. 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
The price is CA $112
CA $496 total
includes taxes & fees
Sep 13 - Sep 14
Broad Street Suite 3|Parking for 3 Vehicles |Walkable |Boho Inspired |Full Kitchen |Huge Living Room
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenwood vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood vacation rentals we have selected for you start as low as CA $255 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation 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 vacation.

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 vacation rentals in Greenwood?

Yes, there are vacation rentals near well known sights in Greenwood, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Greenwood?

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲: This vacation home rental outside of Greenwood is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Petersen Park Beach and McHenry County Fairgrounds.

What are vacation rentals like in Greenwood?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Greenwood. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family gatherings.