Greenwood Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Greenwood

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2892)
"Had a great staycation here. "
The price is AU$407
includes taxes & fees
4 Aug - 5 Aug
Timber Ridge Lodge and Waterpark

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1177)
"Love the Mill Creek! I had a wonderful stay over the fourth of July and really enjoyed the staff."
The price is AU$410
includes taxes & fees
3 Aug - 4 Aug
Mill Creek Hotel

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

10.0 out of 10, Exceptional, (29)
"The property was decorated so nicely, we loved it! Great location with so much to do within walking distance."
The price is AU$1,394
includes taxes & fees
14 July - 15 July
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar

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

9.8 out of 10, Exceptional, (88)
"Great location for walking to shops & restaurants/bars. Comfortable & nicely decorated. Loved the veranda. "
The price is AU$1,597
includes taxes & fees
30 July - 31 July
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Ground- Level Lake Geneva Villa!

9.0 out of 10, Wonderful, (62)
"Weekend trip to enjoy the outdoors. Lots of places for walking "
The price is AU$558
includes taxes & fees
21 July - 22 July
Ground- Level Lake Geneva Villa!

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

10.0 out of 10, Exceptional, (99)
"Would stay again"
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

10.0 out of 10, Exceptional, (6)
Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

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.

*LAKE GENEVA*⛵️ My Lake COMO WATERFRONT☀️ “My Place in the 🌞 Sun”❣️

10.0 out of 10, Exceptional, (62)
"Good location close to Lake Geneva beaches. Nice pool on property."
*LAKE GENEVA*⛵️ My Lake COMO WATERFRONT☀️ “My Place in the 🌞 Sun”❣️

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

9.4 out of 10, Exceptional, (8)
"Communication and check in was flawless.We had three generations for the holidays and this property was ideal for us.Property manager communication was easy and timely."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

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

9.8 out of 10, Exceptional, (185)
"We loved our time at the Downtowner. The rustic modern style was really fun, the rooms were cute and comfortable, and the kitchen was amazing! "
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

Twin Lakes Rental One Block from Lake Elizabeth

9.6 out of 10, Exceptional, (29)
"We had a blast at Marks place. It’s just a short walk to a secluded beach and nearby all the fun stuff in town. The host was so accessible and welcoming. The cottage was well- appointed and very comfortable."
Twin Lakes Rental One Block from Lake Elizabeth

Cozy Cabin in Williams Bay

9.0 out of 10, Wonderful, (60)
"Very convenient to William’s Bay."
Cozy Cabin in Williams Bay

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (84)
"We had an amazing weekend at this house! Was spacious, clean, and well-equipped with everything we needed for a fun and relaxing stay. The location was convenient yet private, making it the perfect spot to unwind with friends. The host was responsive and accommodating, ensuring we had a seamless experience. Highly recommend for anyone looking for a great weekend escape!"
Private Country House near Lake Geneva, Como and Williams Bay

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

10.0 out of 10, Exceptional, (4)
"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."
The price is AU$2,564
includes taxes & fees
23 July - 24 July
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

LAKESIDE GEM ! ONE BLOCK FROM SHORELINE ! in fabulous Lake Geneva .

10.0 out of 10, Exceptional, (2)
"Had a fantastic stay at this stunning new house near the lake. The house is spotless, thoughtfully designed and fully equipped with everything you need for a relaxing and fun-filled stay.The location was perfect, which is just a short walk to the lake and some local restaurants. The patio deck is a perfect spot for morning coffee or an evening cocktail. The neighborhood was quiet and felt very safe. The beds are comfortable, and the kitchen had all the essentials and then some. The host was very...
LAKESIDE GEM ! ONE BLOCK FROM SHORELINE ! in fabulous Lake Geneva .

NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

9.0 out of 10, Wonderful, (98)
"The property was beautiful, great location for walking. Love the decor. The bed was so comfy. Thank you for a great anniversary! "
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

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

10.0 out of 10, Exceptional, (80)
"wonderful experience from beginning to end"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Gorgeous Downtown Baker St Bungalow, Walk Everywhere!!!

10.0 out of 10, Exceptional, (125)
"Beautiful place, excellent hosts, fantastic neighborhood. Our only criticism was not being able to make a fire in the fireplace. One of the many reasons we chose this house was the fireplace feature. We also wanted a front porch, updated kitchen, and a spa tub. This place had all of that!"
Gorgeous Downtown Baker St Bungalow, Walk Everywhere!!!

Stunning Lakeside Retreat: Delavan Lake Home w/ Lake Views & Private Lake Access

10.0 out of 10, Exceptional, (28)
"This beautiful home was just right for 9 high school friends celebrating 55+ years of friendship. The well-equipped kitchen was great for organizing and preparing snacks and meals. Lots of comfy gathering options and plenty of bedrooms and bathrooms! There’s even a great yoga space on the upper level! Highly recommended! "
Stunning Lakeside Retreat: Delavan Lake Home w/ Lake Views & Private Lake Access
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

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 Illinois Railway Museum, or get outside and enjoy nature at Petersen Park Beach. In the wider area, you’ll find McHenry County Fairgrounds and Bull Valley Golf Club.

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.