Holiday Hills Vacation Rentals

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Holiday Hills

Our top choices for Holiday Hills vacation rentals

Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (17)
"Fells like home very cozy calm area definitely a get away relaxing place "
$352 nightly
The price is $373
Sep 8 - Sep 9
Total with taxes and fees
Charming 3-bedroom house in Grayslake
Breathtaking home close to Schaumburg, Chicago
Dining

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (69)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Lake Front 2.20 acre estate Private boat launch with pier
Interior

Lake Front 2.20 acre estate Private boat launch with pier

9.8 out of 10, Exceptional, (17)
"We had a great family vacation here! The property is huge & beautiful. Tons of large clean bedrooms & baths & great rooms. Played pool, foisball & ping pong in garage, pickleball & basketball on court, volleyball & teetherball. This place had everything we were looking for!"
Lake Front 2.20 acre estate Private boat launch with pier
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A heated pool

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

9.4 out of 10, Exceptional, (39)
"The house was very clean and spacious. A lot of activities to do "
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
This is a VACATION spot with a million dollar view!
Exterior

This is a VACATION spot with a million dollar view!

9.8 out of 10, Exceptional, (15)
"The house was beautiful and very close to my sisters house"
$345 nightly
The price is $365
Sep 14 - Sep 15
Total with taxes and fees
This is a VACATION spot with a million dollar view!
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (90)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Outdoor dining

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

10.0 out of 10, Exceptional, (10)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
$1,563 nightly
The price is $1,657
Sep 9 - Sep 10
Total with taxes and fees
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
$192 nightly
The price is $204
Sep 8 - Sep 9
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Spacious Ranch blocks away from downtown McHenry
Fridge, microwave, oven, stovetop

Spacious Ranch blocks away from downtown McHenry

9.8 out of 10, Exceptional, (15)
"Very nice place and host is great "
$331 nightly
The price is $351
Sep 26 - Sep 27
Total with taxes and fees
Spacious Ranch blocks away from downtown McHenry
Spacious 27’ RV on horse farm
Property grounds

Spacious 27’ RV on horse farm

8.6 out of 10, Excellent, (7)
"My stay here was great and I had everything I needed to be comfortable and enjoy myself. I was given a quick tour of the camper and shown how everything works, which was very helpful. I even got shown around the farm and really enjoyed seeing all of the beautiful horses and cute chickens."
$110 nightly
The price is $116
Sep 8 - Sep 9
Total with taxes and fees
Spacious 27’ RV on horse farm
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (51)
"Overall nice stay, the master shower didn’t work but there were 2 other bathrooms, "
Beautiful and spacious lakefront home! Close to everything!
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Smart TV

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

10.0 out of 10, Exceptional, (1)
"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...
$196 nightly
The price is $210
Sep 8 - Sep 9
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
Property grounds

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

9.8 out of 10, Exceptional, (6)
"Home was very clean, cozy and had everything we needed to make our stay the relaxing getaway we hoped for. Lawn could have been mowed before our arrival so we could have enjoyed the beautiful back yard area more."
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Dining

#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

10.0 out of 10, Exceptional, (40)
"Even better than described"
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Tiny Home Retreat with hot tub
Outdoor dining

Tiny Home Retreat with hot tub

8.0 out of 10, Very Good, (2)
"We had the most wonderful time"
$289 nightly
The price is $306
Sep 11 - Sep 12
Total with taxes and fees
Tiny Home Retreat with hot tub
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Interior

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

9.2 out of 10, Wonderful, (53)
"Great space Great Lake view! Lots to do for family entertainment…basketball billiards ping pong plus much much more. "
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Paper towels

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Terrace/patio

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

9.4 out of 10, Exceptional, (107)
"Was a great place to stay for our bachelorette trip! "
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
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 Holiday Hills Hotel Reviews

Find out more about Holiday Hills

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 $116 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Lake Front 2.20 acre estate Private boat launch with pier: Visitors like this Holiday Hills vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a pool table and a hot tub.

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 McHenry Shores Beach Park. 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.