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Our top choices for Oakwood Hills holiday rentals

1. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
The price is £256
includes taxes & fees
16 Aug - 17 Aug
Spacious 3 Bedroom

2. 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 £144
includes taxes & fees
13 Aug - 14 Aug
Little Fox Cottage - A Cozy Riverview Getaway

3. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is £361
includes taxes & fees
23 Aug - 24 Aug
King bed Crystal Lake Mchenry Cary Cozy

4. 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, (9 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
The price is £220
includes taxes & fees
17 Aug - 18 Aug
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

5. 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, (28 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is £176
includes taxes & fees
13 Aug - 14 Aug
This is a VACATION spot with a million dollar view!

6. 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 £211
includes taxes & fees
17 Aug - 18 Aug
The Tailor House

7. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (73 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is £270
includes taxes & fees
8 Sept - 9 Sept
Quaint Bungalow, near Great Lakes Naval Base

8. 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, (2 reviews)
"Cute little apartment over the top of a boba shop. There is a little hidden bedroom with a twin bed on the other side of the living room that was so cozy. In the bedroom there is a King size bed with a very comfortable mattress and plenty of closet space. The bathroom is small but easy to use, and the kitchen is large and roomy. We didn’t get to spend much time at the place but we enjoyed the location and the quiet neighborhood. On site workers were also so helpful when we needed an extension...
United States
Callie C.
The price is £137
includes taxes & fees
13 Aug - 14 Aug
Lovely 1-bedroom apartment with AC in charming Woodstock

9. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (22 reviews)
"Clean, cozy and a very nice central location for our trip around"
United States
Zachary K.
The price is £185
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #2 - Downtown Dundee - Walk to Dining

10. 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)
"Great stay. The loft is situated in an area where it is easy to walk to interesting dining options and stroll the river walk."
United States
Angela D.
The price is £181
includes taxes & fees
16 Aug - 17 Aug
124 Lofts #1 - Downtown Dundee - Walk to Dining

11. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Always a pleasure to stay here when visiting my son!"
United States
Jen C.
The price is £198
includes taxes & fees
13 Aug - 14 Aug
Kildahl House - Boutique Farmhouse Suite #2

12. 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 £315
includes taxes & fees
23 Aug - 24 Aug
Wonder Lake Elegance: Serene 2BR Townhome Retreat

13. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay"
United States
Anonymous traveller
The price is £76
includes taxes & fees
1 Sept - 2 Sept
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

14. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (86 reviews)
"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."
United States
Suzanne H.
The price is £165
includes taxes & fees
13 Aug - 14 Aug
Master qtr close to nature & easy urban facilities

15. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (17 reviews)
"This is a lovely place to call “home base” while visiting Chicago and surrounding communities. Comfortable, clean, quiet and nicely decorated. My little dogs even had a welcome basket! I wish I could have stayed a bit longer"
United States
Thea
The price is £200
includes taxes & fees
30 Aug - 31 Aug
Kildahl House - Boutique Farmhouse Suite #1

16. 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 £263
includes taxes & fees
1 Sept - 2 Sept
The Main Event Game House on the Huntley Square!

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

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
8.0 out of 10, Very good, (1 review)
"Everything was great except not enough pots n pans and ac unit is very loud."
United States
Phuong N.
The price is £258
includes taxes & fees
19 Aug - 20 Aug
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

18. Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
8.6 out of 10, Excellent, (20 reviews)
"The place is very cozy and inviting. There was a smell we thought might have been cat urine on a blanket. Otherwise I'd recommend it."
United States
Matt H.
The price is £181
includes taxes & fees
13 Aug - 14 Aug
Apartment Attached to a 1900 historic Farm house

19. 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 traveller
The price is £281
includes taxes & fees
13 Aug - 14 Aug
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
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

Everything you need to know about Oakwood Hills holiday rentals

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

Oakwood Hills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakwood Hills. 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 Oakwood Hills holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakwood Hills holiday rentals we have selected for you start as low as £165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakwood Hills rentals

At Expedia, we put the best Oakwood Hills holiday 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 Oakwood Hills 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 Oakwood Hills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakwood Hills. 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 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. North Wall Rock Climbing and Moraine Hills State Park 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.