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Oakwood Hills Holiday Rentals

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Our top choices for Oakwood Hills holiday rentals

1. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
9.6 out of 10, Exceptional, (4 reviews)
"Great location, nice place."
United States
Edward L.
The price is NZ$514
includes taxes & fees
16 Nov - 17 Nov
Spacious 3 Bedroom

2. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is NZ$869
includes taxes & fees
16 Nov - 17 Nov
King bed Crystal Lake Mchenry Cary Cozy

3. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
9.8 out of 10, Exceptional, (20 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is NZ$325
includes taxes & fees
17 Nov - 18 Nov
Little Fox Cottage - A Cozy Riverview Getaway

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

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
McHenry
9.2 out of 10, Wonderful, (47 reviews)
"This place was amazing. We had a large group and it did not disappoint. The place was clean and well stocked. The host was so accommodating and the communication was great. We would stay here again for sure."
United States
Darlene C.
The price is NZ$2,603
includes taxes & fees
16 Nov - 17 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

5. 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, (13 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is NZ$587
includes taxes & fees
16 Nov - 17 Nov
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

6. 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 NZ$607
includes taxes & fees
16 Nov - 17 Nov
Wonder Lake Elegance: Serene 2BR Townhome Retreat

7. 124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts #4 - Downtown Dundee - Walk to Dining
West Dundee
9.8 out of 10, Exceptional, (20 reviews)
"Wonderful loft, highly recommend!"
United States
Bret V.
The price is NZ$454
includes taxes & fees
19 Nov - 20 Nov
124 Lofts #4 - Downtown Dundee - Walk to Dining

8. Spacious Creekside Suite Near Chicago

Spacious Creekside Suite Near Chicago
barrington hill
The price is NZ$514
includes taxes & fees
22 Nov - 23 Nov
Spacious Creekside Suite Near Chicago

9. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is NZ$437
includes taxes & fees
16 Nov - 17 Nov
124 Lofts #1 - Downtown Dundee - Walk to Dining

10. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay at the Kildahl House! It is clean, cozy, charming. The location is perfect and accessible to to the river and downtown. I loved the connections Andy and Suzanne have made with local businesses to make your stay even more enjoyable!"
United States
Elise L.
The price is NZ$473
includes taxes & fees
7 Dec - 8 Dec
Kildahl House - Boutique Farmhouse Suite #1

11. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"I would stay here again in a heartbeat!"
United States
Rebecca R.
The price is NZ$473
includes taxes & fees
6 Dec - 7 Dec
Kildahl House - Boutique Farmhouse Suite #2

12. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is NZ$437
includes taxes & fees
23 Nov - 24 Nov
The Main Event Game House on the Huntley Square!

13. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (60 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is NZ$420
includes taxes & fees
16 Nov - 17 Nov
The Tailor House

14. This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
9.8 out of 10, Exceptional, (34 reviews)
"This was an amazing property right on the water. It was clean, the host was very helpful and answered questions in a timely manner. We came when it rained which was unfortunate but we still enjoyed our time there!"
United States
Christina C.
The price is NZ$547
includes taxes & fees
16 Nov - 17 Nov
This is a VACATION spot with a million dollar view!

15. 5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8

5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8
Wonder Lake
9.4 out of 10, Exceptional, (13 reviews)
"Place was really nice and hosts were very friendly and helpful."
United States
Olivia F.
The price is NZ$924
includes taxes & fees
16 Nov - 17 Nov
5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8

16. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (28 reviews)
"Lovely stay! Great location!"
United States
David K.
The price is NZ$454
includes taxes & fees
19 Nov - 20 Nov
124 Lofts #3 - Downtown Dundee - Walk to Dining

17. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
9.4 out of 10, Exceptional, (3 reviews)
"Great place"
United States
Sthendall M.
The price is NZ$591
includes taxes & fees
6 Dec - 7 Dec
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

18. Lovely 1-bedroom apartment with AC in charming Woodstock

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.6 out of 10, Excellent, (4 reviews)
"Everything was great! The property is close to everything and was easy to access. The only drawback was the air conditioning in the bedroom was very loud. Other than that no problems."
United States
Beth B.
The price is NZ$311
includes taxes & fees
18 Nov - 19 Nov
Lovely 1-bedroom apartment with AC in charming Woodstock

19. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (24 reviews)
"It was an absolute beautiful place and I’d stay again if I’m ever in the area."
United States
steve m.
The price is NZ$437
includes taxes & fees
16 Nov - 17 Nov
124 Lofts #2 - Downtown Dundee - Walk to Dining

20. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (77 reviews)
"House was clean. Nice layout. Woodwork is very charming. Fenced in backyard was a lovely place to toss around a frisbee and kick a soccer ball. House was close to a grocery store and other amenities. Kitchen was stocked with everything one needs. Recommend others staying here if you need to be in the area."
United States
Benjamin O.
The price is NZ$602
includes taxes & fees
23 Nov - 24 Nov
Quaint Bungalow, near Great Lakes Naval Base
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 Oakwood Hills Hotel Reviews

Find out more about Oakwood Hills

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakwood Hills holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakwood Hills. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakwood Hills. Seeing all the best attractions is bound to make you fall in love with Oakwood Hills. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakwood Hills short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oakwood Hills?

Yes, there are holiday rentals close to the most popular sights in Oakwood Hills, 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 Oakwood Hills has to offer?

Pleasant 3-bedroom house with occupied basement separate entrance.: This holiday home rental outside of Oakwood Hills has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Oakwood Hills?

Explore the area and family-friendly sights such as Santa's Village, or get out into nature at a spot like Three Oaks Recreation Area. Moraine Hills State Park and Main Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Oakwood Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakwood Hills. Holiday rentals feature extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.