Holiday Rentals in Oakwood Hills

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Oakwood Hills

Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
10.0 out of 10, Exceptional, (8)
"A pleasant and welcoming vibe near the lake. Very clean. Lots of special touches. Caring and attentive host. We would stay here again. "
United States
Marcia B.
The price is €313
includes taxes & fees
26 Oct - 27 Oct
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
10.0 out of 10, Exceptional, (13)
"Our family loved this property. Perfect space for our family of 15; the pool was the icing on the cake. We appreciated all the amenities , and the extra touch of beautiful fresh flowers did not go unnoticed. Great setup in the kitchen for preparing meals. The kiddos loved the ability to play video games. Great place. "
United States
Diane L.
The price is €1,601
includes taxes & fees
23 Oct - 24 Oct
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.2 out of 10, Wonderful, (41)
"Very comfortable… enjoyed the property to the upmost.."
United States
Debra H.
The price is €1,149
includes taxes & fees
27 Oct - 28 Oct
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Roxan Corner
8.6 out of 10, Excellent, (44)
"We enjoyed our stay! The neighborhood felt safe and we very much loved the space as they made it quite inviting with books and candles. I would have loved more blankets on the beds but overall we had a great stay!"
United States
Michelle V.
Roxan Corner
Cozy W Front Porch DT Libertyville near Naval Base
9.6 out of 10, Exceptional, (18)
"Clean and good communication with host. "
United States
Shavonda O.
Cozy W Front Porch DT Libertyville near Naval Base
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
10.0 out of 10, Exceptional, (3)
"Barrington was an adorable town tucked away just an hour out of Chicago. This property is the perfect spot for a getaway with your loved one. My boyfriend and I had an amazing weekend and will definitely stop by again in the future!"
United States
Cierra F.
The price is €186
includes taxes & fees
29 Oct - 30 Oct
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
9.2 out of 10, Wonderful, (57)
"We had a great time! Jeff was easy to communicate with and accommodating to our group. While the property is beautiful, folks should know you cannot swim at the dock. We did rent a pontoon which provided lots of swimming opportunity and fun! Thanks again for a great stay!"
United States
Kelsey H.
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
9.4 out of 10, Exceptional, (109)
"Was a great place to stay for our bachelorette trip! "
United States
Courtney W.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
This is a VACATION spot with a million dollar view!
9.8 out of 10, Exceptional, (16)
"The house was beautiful and very close to my sisters house"
United States
Jenifer D.
The price is €226
includes taxes & fees
23 Oct - 24 Oct
This is a VACATION spot with a million dollar view!
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (69)
"Beautiful, quiet space."
United States
Mary
The price is €162
includes taxes & fees
3 Nov - 4 Nov
Master qtr close to nature & easy urban facilities
Fox River/Chain of Lakes Waterfront Home with Hot Tub
10.0 out of 10, Exceptional, (37)
"Loved our stay, stocked kitchen, great backyard and big tub. "
United States
Michael S.
Fox River/Chain of Lakes Waterfront Home with Hot Tub
Large Group Retreat w/ secluded party room and private pool
7.8 out of 10, Good, (22)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
United States
Derek K.
Large Group Retreat w/ secluded party room and private pool
Charming 3-bedroom house in Grayslake
9.8 out of 10, Exceptional, (20)
"Fells like home very cozy calm area definitely a get away relaxing place "
United States
Paola
The price is €329
includes taxes & fees
3 Nov - 4 Nov
Charming 3-bedroom house in Grayslake
Lake Front 2.20 acre estate Private boat launch with pier
9.8 out of 10, Exceptional, (20)
"Great stay. Everything that was listed was there and more. We utilized all of their courts/fields throughout the weekend and it was a really great time."
United States
Jordan P.
Lake Front 2.20 acre estate Private boat launch with pier
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
9.8 out of 10, Exceptional, (17)
"Great property overall. The host was very accommodating and I highly recommend. "
United States
Jamie H.
The price is €574
includes taxes & fees
23 Oct - 24 Oct
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
Beautiful and spacious lakefront home! Close to everything!
9.6 out of 10, Exceptional, (53)
"A three night stay We were comfortable and pleased with all the amenities. Fishing by the dock, kayaking and enjoying an adult beverage. A magical place to celebrate a new stage. Just one hour away but distant enough to relax the mind "
United States
JM G.
Beautiful and spacious lakefront home! Close to everything!
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.
The price is €451
includes taxes & fees
23 Oct - 24 Oct
Randolph Hotel Capone Suite 201
Spacious Ranch blocks away from downtown McHenry
9.8 out of 10, Exceptional, (16)
"Great home and perfect location. "
United States
Steve B.
The price is €288
includes taxes & fees
23 Oct - 24 Oct
Spacious Ranch blocks away from downtown McHenry
Lakefront home with firepit, 2 kitchens, & 2 W/Ds
8.8 out of 10, Excellent, (16)
"The house and location was great! Had a wonderful time!"
United States
Pamela I.
Lakefront home with firepit, 2 kitchens, & 2 W/Ds
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.
Save an average of 15% on thousands of hotels when you're signed in

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 €162 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?

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.: This holiday home rental outside of Oakwood Hills is located near skiing, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Crystal Lake City Hall 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.