Greenwood Vacation Rentals

Start date: Check-in selected.
End date: Check-out

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Greenwood

Our top choices for Greenwood vacation rentals

Timber Ridge Lodge and Waterpark
Water park

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2979)
"Nice stay for a short weekend getaway. "
$184 nightly
The price is $205
Sep 23 - Sep 24
Total with taxes and fees
Timber Ridge Lodge and Waterpark
Mill Creek Hotel
Indoor spa tub

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1197)
"We loved the area and all the surroundings activities. Awesome place to visit."
$183 nightly
The price is $207
Oct 1 - Oct 2
Total with taxes and fees
Mill Creek Hotel
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar
Interior

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar

10.0 out of 10, Exceptional, (30)
"We came to Wisconsin for a bachelorette party! This place was described perfectly and was absolutely perfect for our girls! We are very very pleased and would recommend this highly!"
$725 nightly
The price is $823
Sep 10 - Sep 11
Total with taxes and fees
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Beach

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

9.8 out of 10, Exceptional, (91)
"A few wonderful days spent with family in a welcoming home. I must have experienced this again."
$567 nightly
The price is $644
Sep 15 - Sep 16
Total with taxes and fees
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Fridge, microwave, oven, stovetop

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

9.8 out of 10, Exceptional, (104)
"Out bachelor party stay was fantastic, everything about the trip was a breeze! "
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Fridge, microwave, oven, stovetop

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

9.8 out of 10, Exceptional, (190)
"I booked this property for a bachelorette party and everyone had a great time! It is in the perfect location for being able to walk to everything, which was perfect for a large group! The kitchen/living room space was perfect for all the girls to hang out together and play games. Parking is very limited, but there is a free lot nearby that we were able to utilize as well. "
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
6 bedrooms, desk, iron/ironing board, travel crib

Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

2.5 star property
10.0 out of 10, Exceptional, (8)
"The house was amazing; the owner went above and beyond helping with all of our questions. The views were amazing. We can't wait to go back. "
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A heated pool

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

9.4 out of 10, Exceptional, (39)
"The house was very clean and spacious. A lot of activities to do "
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

2.0 star property
9.4 out of 10, Exceptional, (11)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Private Country House near Lake Geneva, Como and Williams Bay
Outdoor dining

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (89)
"Good place to stay nice location "
Private Country House near Lake Geneva, Como and Williams Bay
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Indoor pool, a heated pool

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

9.6 out of 10, Exceptional, (11)
"The house was great. The pool temp was very warm when we arrived we did our best to cool it down. We really enjoyed the stay."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Fridge, microwave, oven, stovetop

Chic 3 bedroom Get-a-way in downtown Lake Geneva

9.8 out of 10, Exceptional, (7)
$284 nightly
The price is $322
Sep 8 - Sep 9
Total with taxes and fees
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Charming getaway with panoramic lake views. 5 minutes from downtown Lake Geneva.
Marina

Charming getaway with panoramic lake views. 5 minutes from downtown Lake Geneva.

10.0 out of 10, Exceptional, (18)
"The unit was very well appointed and beautifully decorated. We appreciated the higher quality bedding, towels and blankets and the welcoming snacks. The location was perfect and we enjoyed the patio. "
Charming getaway with panoramic lake views. 5 minutes from downtown Lake Geneva.
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Outdoor dining

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

10.0 out of 10, Exceptional, (10)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
$1,563 nightly
The price is $1,657
Sep 9 - Sep 10
Total with taxes and fees
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (90)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
THE ULTIMATE 6 BEDROOM LAKEHOUSE
Terrace/patio

THE ULTIMATE 6 BEDROOM LAKEHOUSE

9.6 out of 10, Exceptional, (38)
"Simply the best stay we have ever had. Thank you so much! "
$955 nightly
The price is $1,065
Sep 17 - Sep 18
Total with taxes and fees
THE ULTIMATE 6 BEDROOM LAKEHOUSE
Excellent getaway. Lake front home with Stunning lake views, come make memories!
Interior

Excellent getaway. Lake front home with Stunning lake views, come make memories!

9.2 out of 10, Wonderful, (26)
"The home and location were as described….arrival check in was great….every amenity imaginable was available in the home.The views of the lake were terrific ….only item lacking was blinds on the bedroom windows…master had them others were shears or nothing….so we rose early with the sunrise!We would book this house again if we are looking in the area….thank you to the host"
Excellent getaway. Lake front home with Stunning lake views, come make memories!
Walk to downtown/beach Huge historic house perfect for large groups or families
Terrace/patio

Walk to downtown/beach Huge historic house perfect for large groups or families

10.0 out of 10, Exceptional, (27)
"The home is as lovely as described. Very spacious, clean, and great location. We enjoyed our stay very much."
$784 nightly
The price is $889
Sep 8 - Sep 9
Total with taxes and fees
Walk to downtown/beach Huge historic house perfect for large groups or families
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenwood Hotel Reviews

Find out more about Greenwood

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $205 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage: This vacation home rental outside of Greenwood is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

What can I see and do in Greenwood?

While exploring the area, visit family-friendly sights like Dan Patch Stables, or get outside and enjoy nature at Petersen Park Beach. In the larger area, you’ll find McHenry County Fairgrounds and Bull Valley Golf Club.

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.