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Oakwood Hills Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Oakwood Hills vacation rentals

Outdoor dining

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 ￥22,572
￥55,837 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 3 Bedroom
House | 2 bedrooms

2. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is ￥22,506
￥71,497 total
includes taxes & fees
Aug 17 - Aug 18
King bed Crystal Lake Mchenry Cary Cozy
Outdoor dining

3. 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 ￥22,704
￥35,592 total
includes taxes & fees
Aug 9 - Aug 10
Little Fox Cottage - A Cozy Riverview Getaway
Property grounds

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

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is ￥173,437
￥642,822 total
includes taxes & fees
Aug 11 - Aug 12
Perfect Family Getaway: Spacious 5BR Home in Barrington
Interior

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, (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 ￥26,974
￥46,808 total
includes taxes & fees
Aug 12 - Aug 13
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
TV

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 ￥36,554
￥66,812 total
includes taxes & fees
Aug 17 - Aug 18
Wonder Lake Elegance: Serene 2BR Townhome Retreat
Marina

7. 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, (27 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is ￥31,534
￥56,980 total
includes taxes & fees
Aug 10 - Aug 11
This is a VACATION spot with a million dollar view!
Exterior

8. Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Barrington
The price is ￥425,709
￥914,559 total
includes taxes & fees
Sep 5 - Sep 6
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
1 bedroom, desk, iron/ironing board, WiFi

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 ￥30,430
￥38,260 total
includes taxes & fees
Aug 11 - Aug 12
124 Lofts #4 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

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 ￥30,430
￥38,260 total
includes taxes & fees
Aug 11 - Aug 12
124 Lofts #1 - Downtown Dundee - Walk to Dining
Property grounds

11. Kildahl House - Boutique Farmhouse Suite #3

Kildahl House - Boutique Farmhouse Suite #3
West Dundee
10.0 out of 10, Exceptional, (21 reviews)
"Everything was perfect! Great location and would stay there again. "
United States
EDWARD P.
The price is ￥32,953
￥41,753 total
includes taxes & fees
Aug 12 - Aug 13
Kildahl House - Boutique Farmhouse Suite #3
Marina

12. Pistakee Marina Boat House

Pistakee Marina Boat House
Fox Lake
7.2 out of 10, Good, (5 reviews)
"Came with the grandkids to visit Volo from south Indiana, short stay. Exactly what we needed, no more no less. Kids enjoyed and so did the adults. Would definitely stay again if in the area."
United States
Donald C.
The price is ￥21,073
￥105,199 total
includes taxes & fees
Aug 10 - Aug 11
Pistakee Marina Boat House
Exterior

13. 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 ￥26,489
￥47,456 total
includes taxes & fees
Aug 17 - Aug 18
The Tailor House
Property grounds

14. 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 ￥32,953
￥41,251 total
includes taxes & fees
Aug 31 - Sep 1
Kildahl House - Boutique Farmhouse Suite #1
1 bedroom

15. Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (15 reviews)
"Big room with a kitchen,"
United States
Anonymous traveler
The price is ￥16,973
￥18,779 total
includes taxes & fees
Sep 1 - Sep 2
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Private kitchen

16. 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
The price is ￥43,359
￥60,490 total
includes taxes & fees
Aug 13 - Aug 14
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Exterior

17. 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 ￥32,322
￥55,142 total
includes taxes & fees
Sep 1 - Sep 2
The Main Event Game House on the Huntley Square!
Exterior detail

18. 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)
"A 5 star property. "
United States
James A.
The price is ￥18,305
￥33,604 total
includes taxes & fees
Aug 13 - Aug 14
Master qtr close to nature & easy urban facilities
Private kitchen

19. 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 ￥23,651
￥28,408 total
includes taxes & fees
Aug 10 - Aug 11
Lovely 1-bedroom apartment with AC in charming Woodstock
Outdoor dining

20. Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is ￥36,106
￥66,672 total
includes taxes & fees
Aug 9 - Aug 10
Tiny Home Retreat with hot tub
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

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

10/10 Excellent
"Wonderful. 5 year old loved it"
Denise Blair 2-night trip
Posted 5 hours ago
Great Wolf Lodge Illinois

Find out more about Oakwood Hills

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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. Crystal Lake City Hall and Moraine Hills State Park 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.