Oakwood Hills Vacation Rentals

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Our top choices for Oakwood Hills vacation rentals

Vacation Home in Waukegan

Home -2 bedroom, 4k projector
2.0 star property
10.0 out of 10, Exceptional, (2)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
$228 nightly
The price is $242
Dec 14 - Dec 15
Total with taxes and fees
Home -2 bedroom, 4k projector
10.0 out of 10, Exceptional, (2)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
$256 nightly
The price is $271
Dec 14 - Dec 15
Total with taxes and fees
Wonder Lake Elegance: Serene 2BR Townhome Retreat
9.8 out of 10, Exceptional, (6)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
United States
Sarah S.
$149 nightly
The price is $160
Dec 14 - Dec 15
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Apartment in Fox Lake

Randolph Hotel Capone Suite 201
6.0 out of 10, (2)
"Staying in the Round Lake Beach area to visiting family. Room is great and clean. Pretty view of Fox Lake. Only draw back is it is over a bar. Karaoke comes right up through the floor. Not to much of a problem as the bar closes at 11:00. So just have to suffer through the drunken super star want a be singers. It is good for some laughs. Over all I would recommend this place in a heartbeat. "
United States
Daniel H.
$433 nightly
The price is $480
Dec 19 - Dec 20
Total with taxes and fees
Randolph Hotel Capone Suite 201
9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
United States
Joshua K.
$176 nightly
The price is $187
Dec 25 - Dec 26
Total with taxes and fees
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (66)
"Great place and great price. Lots of restaurants around. Minutes from the highway for city access."
United States
Joseph B.
$313 nightly
The price is $332
Dec 15 - Dec 16
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (11)
"The loft is a great place to stay and we can’t wait to return! "
United States
Chad G.
$198 nightly
The price is $214
Dec 14 - Dec 15
Total with taxes and fees
Hip Urban Loft-Small Town Charm -124 LOFTS #4
9.8 out of 10, Exceptional, (19)
"So easy to get to, right in the water. Has a dock for your boat. Sonja is very welcoming. "
United States
Kristina H.
$240 nightly
The price is $254
Dec 14 - Dec 15
Total with taxes and fees
This is a VACATION spot with a million dollar view!

Vacation Home in South Elgin

Riverfront rental
9.8 out of 10, Exceptional, (34)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
$197 nightly
The price is $209
Dec 14 - Dec 15
Total with taxes and fees
Riverfront rental

Vacation Home in Cary

Spacious 3 Bedroom
2.0 star property
$279 nightly
The price is $296
Dec 19 - Dec 20
Total with taxes and fees
Spacious 3 Bedroom
$203 nightly
The price is $217
Dec 14 - Dec 15
Total with taxes and fees
Stylish, Sun-Filled Retreat - Minutes to O’Hare! 2 bed, 2bath with amenities

Apartment in Arlington Heights

Recharge in This Charming 1BR Apt
$150 nightly
The price is $162
Dec 16 - Dec 17
Total with taxes and fees
Recharge in This Charming 1BR Apt
9.6 out of 10, Exceptional, (21)
"Great home and perfect location. "
United States
Steve B.
$309 nightly
The price is $327
Dec 14 - Dec 15
Total with taxes and fees
Spacious Ranch blocks away from downtown McHenry
2.0 star property
$371 nightly
The price is $393
Dec 16 - Dec 17
Total with taxes and fees
King bed Crystal Lake Mchenry Cary Cozy
8.6 out of 10, Excellent, (17)
"If I had to choose a word, it would be thoughtful. From the extra toiletries and towels to the coffee selection and soft bedding, it was an enjoyable stay. It was also wonderful to feel like my doggo was not just allowed but welcomed. Bowls and bed provided, with a short trail cut for us to explore. "
United States
Mary M.
$249 nightly
The price is $264
Dec 14 - Dec 15
Total with taxes and fees
Apartment Attached to a 1900 historic Farm house
10.0 out of 10, Exceptional, (7)
"The new place was amazing. I wished my work trip was longer so I could have stayed longer. The owner was also very responsive with messages and was great to talk to. I would definitely stay again the next time I'm in town. "
United States
Adam M.
$256 nightly
The price is $271
Dec 14 - Dec 15
Total with taxes and fees
Elegant New Home Near Lakes - Relax & Unwind!

Vacation Home in Woodstock

The Tailor House
9.8 out of 10, Exceptional, (48)
"I really enjoyed the place "
United States
Ahmed A.
$264 nightly
The price is $280
Dec 15 - Dec 16
Total with taxes and fees
The Tailor House
2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
$530 nightly
The price is $543
Jan 4 - Jan 5, 2026
Total with taxes and fees
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games

Vacation Home in Lake Villa

Hot Tub Retreats
2.0 star property
$224 nightly
The price is $238
Dec 14 - Dec 15
Total with taxes and fees
Hot Tub Retreats
10.0 out of 10, Exceptional, (17)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
United States
Kelly F.
$205 nightly
The price is $217
Dec 14 - Dec 15
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
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 vacation rentals

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

Oakwood Hills vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakwood Hills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakwood Hills rentals

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

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 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?

Home -2 bedroom, 4k projector: 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 Fox River Preserve. Three Oaks Recreation Area 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.