Default HTG hotel image

Oakwood Hills Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Oakwood Hills vacation rentals

A wooden deck with a table and chairs, surrounded by lush greenery and trees.

1. 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 ￥16,398
￥48,121 total
includes taxes & fees
Oct 25 - Oct 26
Spacious 3 Bedroom
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

2. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (19 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is ￥21,684
￥34,572 total
includes taxes & fees
Oct 26 - Oct 27
Little Fox Cottage - A Cozy Riverview Getaway
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

3. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is ￥17,316
￥65,388 total
includes taxes & fees
Oct 21 - Oct 22
King bed Crystal Lake Mchenry Cary Cozy
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

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 ￥86,705
￥226,991 total
includes taxes & fees
Oct 21 - Oct 22
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A two-story house with a front porch, a stone exterior on the right side, and a green door.

5. 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, (21 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 ￥30,117
￥53,084 total
includes taxes & fees
Nov 4 - Nov 5
The Main Event Game House on the Huntley Square!
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

6. 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 ￥33,129
￥55,940 total
includes taxes & fees
Oct 21 - Oct 22
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
Living area

7. 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 ￥29,366
￥57,999 total
includes taxes & fees
Oct 21 - Oct 22
Wonder Lake Elegance: Serene 2BR Townhome Retreat
A lakeside deck with chairs and a table, a wooden dock extending into the water, and a covered area in the background.

8. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is ￥35,570
￥98,900 total
includes taxes & fees
Nov 3 - Nov 4
Waterfront - Private Dock - Two Suites
A bedroom with a brick wall, a bed, a desk, and a window with a view.

9. 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)
"Awesome loft. Perfect for an overnight stay. Convenient parking and lots of restaurants to choose from."
United States
Shannon
The price is ￥30,592
￥38,464 total
includes taxes & fees
Oct 21 - Oct 22
124 Lofts #4 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

10. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"Everything was as described, great location too! "
United States
Freddy M.
The price is ￥33,129
￥41,975 total
includes taxes & fees
Oct 21 - Oct 22
Kildahl House - Boutique Farmhouse Suite #1
A wicker tray with a pitcher and glasses on a wooden table on a porch.

11. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (20 reviews)
"Wonderful place to stay and the host was very welcoming and easy to work with!"
United States
Kevin B.
The price is ￥33,129
￥41,639 total
includes taxes & fees
Oct 21 - Oct 22
Kildahl House - Boutique Farmhouse Suite #4
A Cadillac SUV parked on a paved driveway with a gated entrance, surrounded by trees with autumn foliage.

12. Perfect Family Getaway: Spacious 5BR Home in Barrington

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is ￥118,883
￥580,960 total
includes taxes & fees
Oct 21 - Oct 22
Perfect Family Getaway: Spacious 5BR Home in Barrington
A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

13. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (57 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is ￥20,289
￥39,981 total
includes taxes & fees
Oct 27 - Oct 28
The Tailor House
A two-story house with a stone chimney, a front porch with steps, and a flag.

14. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (76 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is ￥21,399
￥56,276 total
includes taxes & fees
Oct 25 - Oct 26
Quaint Bungalow, near Great Lakes Naval Base
A house by a lake with docked boats and a flag.

15. 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)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is ￥71,330
￥105,665 total
includes taxes & fees
Oct 23 - Oct 24
This is a VACATION spot with a million dollar view!
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

16. 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 ￥28,056
￥35,623 total
includes taxes & fees
Nov 15 - Nov 16
124 Lofts #1 - Downtown Dundee - Walk to Dining
Private kitchen

17. Charming 2-bedroom house with WiFi, AC in fabulous Woodstock

Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Woodstock
8.0 out of 10, Very good, (1 review)
"I was very surprised that the property was by itself on a 2 lane road. We initially drove past it because there was nothing on the side of the road with the address. It was next to an odd and ugly"building." It was less than 10 minutes frim town, which was good. The house was clean, but REEKED of mildew. We bought stuff to help with the smell (which we left for future guests), but it was still bad. There was no toaster or microwave, and there was someone elase's Culver's in the freezer....
United States
Anonymous traveler
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A red house with a porch, a wooden staircase, and a flag.

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

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.0 out of 10, Very good, (3 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 ￥23,777
￥28,559 total
includes taxes & fees
Oct 21 - Oct 22
Lovely 1-bedroom apartment with AC in charming Woodstock
A modern living room with a dining area, a sofa, a TV, and a fireplace.

19. Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Elgin
10.0 out of 10, Exceptional, (25 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is ￥35,665
￥78,448 total
includes taxes & fees
Nov 17 - Nov 18
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

20. ✨ 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 ￥19,021
￥53,083 total
includes taxes & fees
Nov 2 - Nov 3
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakwood Hills Hotel Reviews

Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

10/10 Excellent
"Very clean and comfortable. The rooms are very spacious. I really enjoy staying there when we land in Chicago."
Johanna 1-night trip
Posted 1 hour ago
Hyatt Place Chicago/ Schaumburg

Find out more about Oakwood Hills

Search for holiday rentals in Oakwood Hills on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakwood Hills using one of the methods below:

  • View our selection of featured holiday rentals in Oakwood Hills
  • Use the map to find apartments and other holiday homes in the Oakwood Hills neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakwood Hills while they last

Look no further and take a look at our great range of rental properties in Oakwood Hills!

Frequently asked questions

Can I find vacation rentals in Oakwood Hills?

Yes, you can find vacation rentals close to popular points of interest in Oakwood Hills, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Oakwood Hills has to offer?

Pleasant 3-bedroom house with occupied basement separate entrance.: Visitors like this Oakwood Hills vacation home rental. It 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 larger area.

What’s a vacation rental in Oakwood Hills like?

Vacation rentals are private properties you can book for a long or short time in Oakwood Hills. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.