Holiday Hills Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

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Our top choices for Holiday Hills vacation rentals

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

1. Spacious 3 Bedroom

Cary

Dan K.

$271 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Fox River Grove

Jeff P.

$166 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

3. King bed Crystal Lake Mchenry Cary Cozy

Cary

$446 nightly

Nov 9 - Nov 10

Total with taxes and fees

4. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake

Ken S.

$320 nightly

Nov 8 - Nov 9

Total with taxes and fees

A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

5. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

McHenry

Cj D.

$309 nightly

Nov 8 - Nov 9

Total with taxes and fees

A house by a lake with docked boats and a flag.

6. This is a VACATION spot with a million dollar view!

fox lake

Jason C.

$288 nightly

Nov 11 - Nov 12

Total with taxes and fees

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

7. The Tailor House

Woodstock

Brittany H.

$221 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story house with a swimming pool, outdoor seating, and a stone chimney.

8. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

McHenry

Darlene C.

$1,275 nightly

Nov 9 - Nov 10

Total with taxes and fees

A kitchen with a view of a lake, wooden cabinets, a dining area with a table and chairs, and a kitchen island.

9. 5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8

Wonder Lake

Olivia F.

$474 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story house with a stone chimney, a front porch with steps, and a flag.

10. Quaint Bungalow, near Great Lakes Naval Base

Mundelein

Benjamin O.

$309 nightly

Nov 8 - Nov 9

Total with taxes and fees

A red house with a porch, a wooden staircase, and a flag.

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

Woodstock

Beth B.

$156 nightly

Nov 9 - Nov 10

Total with taxes and fees

A two-story house with a front porch, a stone exterior on the right side, and a green door.

12. The Main Event Game House on the Huntley Square!

Huntley

BENJAMIN B.

$224 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a television on a stand, a potted plant, a glass coffee table, and a window with curtains.

13. Apartment Attached to a 1900 historic Farm house

Old Mill Creek

jennifer c.

$211 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

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

Chicago

Anonymous traveler

$68 nightly

Nov 19 - Nov 20

Total with taxes and fees

A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

15. Richmond No. 267 Boutique Loft Apartment

Richmond

Ernesta T.

$257 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

West Dundee

Haggard A.

$198 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with a bed, a desk, a chair, a sofa, and a lamp.

17. 124 Lofts #2 - Downtown Dundee - Walk to Dining

West Dundee

steve m.

$184 nightly

Dec 3 - Dec 4

Total with taxes and fees

A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

18. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Libertyville

$534 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wicker tray with a pitcher and glasses on a wooden table on a porch.

19. Kildahl House - Boutique Farmhouse Suite #2

West Dundee

Rebecca R.

$232 nightly

Dec 6 - Dec 7

Total with taxes and fees

20. Kildahl House - Boutique Farmhouse Suite #1

West Dundee

Elise L.

$231 nightly

Dec 7 - Dec 8

Total with taxes and fees

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Find vacation rentals that suit your style

Top Holiday Hills Hotel Reviews

A hotel lobby with a reception desk, seating area, and a television.

Holiday Inn Express Hotel & Suites, a Lake Zurich-Barrington by IHG

Lake Zurich

10/10 Excellent

Ian

A modern living room with a staircase, a sofa, a coffee table, and a fireplace.

Country Inn & Suites by Radisson, Crystal Lake, IL

Crystal Lake

10/10 Excellent

Megan

A spacious indoor area with multiple seating arrangements, including tables and chairs, and a herringbone patterned floor.

Holiday Inn Chicago Nw Crystal Lk Conv Ctr by IHG

Crystal Lake

10/10 Excellent

Laura

A modern hotel lobby with a reception desk, seating area, and a large flat-screen TV.

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

Hoffman Estates

10/10 Excellent

Stacy

A hotel lobby with multiple seating areas, including tables and chairs, a sofa, and a reception desk.

Hampton Inn & Suites Chicago-Libertyville

Libertyville

10/10 Excellent

Deborah

A compact kitchen with a dining table, a microwave, a coffee maker, and a refrigerator.

Sonesta Simply Suites Chicago Libertyville

Libertyville

10/10 Excellent

Karla

A buffet with various food items, including omelets and other dishes, served in metal trays.

Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG

Algonquin

10/10 Excellent

Anonymous traveler

A modern indoor swimming pool with clear blue water, surrounded by lounge areas and large windows offering views.

Hampton Inn & Suites Chicago Deer Park

Barrington

10/10 Excellent

The breakfast here is THE BEST were have ever had in this price range and area with a lot of options, large area and neat. The rooms are really big. We are a party is 6 and the room was more than sufficient for 6. The beds are clean and restrooms are very well stocked. Staff is really courteous and accommodating. The room had both a microwave and a fridge, which you don't find both of town in rooms in many places. This helped us as we has elders and kids in our party. Very highly recommend hotel

Ramasastry

An outdoor patio with a fire pit, two chairs, a table, and a striped umbrella.

HARMONY INN

Huntley

10/10 Excellent

I felt comfortable, safe and well taken care of at the Harmony Inn. Stepping out of my room into the kitchen and on through the doors to the patio was a pleasure (fixing a cup of tea and grabbing a homemade muffin - all included - as I headed to the outdoor seating area, complete with gas heater). Then I attempted to do a little painting of the flowers. There were other snacks including fruit and yogurt😁. Dave, our gracious host, showed me how to feed the ducks and geese which also live on...

Nikki

A modern restaurant with a bar area, a large dining table with chairs, and a fireplace.

Hampton Inn & Suites Chicago/Lincolnshire

Lincolnshire

10/10 Excellent

KATHY

A modern hotel room with a large mirror, a bathtub, a flat-screen TV, a sofa, and a large window.

AmericInn by Wyndham Woodstock IL

Woodstock

10/10 Excellent

Anonymous traveler

A hotel room with a bathtub, a bed, a nightstand, and a window with curtains.

Comfort Suites Grayslake near Libertyville North

Wildwood

10/10 Excellent

Timothy

A spacious lobby with a central reception area, a shop, and potted plants.

Hilton Garden Inn Lake Forest Mettawa

Lake Forest

10/10 Excellent

Anonymous traveler

A hotel room with a bed, a sofa, a desk, and a television.

Wingate by Wyndham Gurnee

Gurnee

10/10 Excellent

Kathy

Find out more about Holiday Hills

Everything you need to know about Holiday 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 Holiday 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 Holiday Hills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Holiday Hills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Holiday 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 Holiday 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 $75 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 Holiday Hills rentals

At Expedia, we put the best Holiday 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 Holiday 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 Holiday 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 Holiday 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 Holiday Hills?

Yes, we have vacation rentals near popular sights in Holiday Hills, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Holiday Hills has to offer?

Pleasant 3-bedroom house with occupied basement separate entrance.: Visitors like this Holiday 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 Holiday Hills?

Explore the area and family-friendly sights such as Six Flags Great America, or get out into nature at a spot like Petersen Park Beach. Moraine Hills State Park and Volo Auto Museum are a couple of places you'll find in the larger area.

What’s a vacation rental in Holiday Hills like?

Vacation rentals are private properties you can stay in for short or long periods in Holiday Hills. Vacation rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for small groups.