Holiday Hills Vacation Rentals

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Holiday Hills Vacation Homes

Our top choices for Holiday Hills vacation homes

Elegant New Home Near Lakes - Relax & Unwind!
TV

Elegant New Home Near Lakes - Relax & Unwind!

10.0 out of 10, Exceptional, (5)
"Beautiful condo close to Wonder Lake. I would recommend this property to everyone."
The price is CA $302
CA $525 total
includes taxes & fees
Sep 7 - Sep 8
Elegant New Home Near Lakes - Relax & Unwind!
Pistakee Marina Boat House
Coffee/tea maker, cookware/dishes/utensils

Pistakee Marina Boat House

7.2 out of 10, Good, (5)
"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."
The price is CA $35
CA $556 total
includes taxes & fees
Aug 21 - Aug 22
Pistakee Marina Boat House
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...
The price is CA $155
CA $269 total
includes taxes & fees
Aug 21 - Aug 22
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
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"
The price is CA $178
CA $420 total
includes taxes & fees
Aug 24 - Aug 25
Tiny Home Retreat with hot tub
Quaint Bungalow, near Great Lakes Naval Base
Dining

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (63)
"Great experience, lots of cooking materials "
The price is CA $186
CA $453 total
includes taxes & fees
Aug 23 - Aug 24
Quaint Bungalow, near Great Lakes Naval Base
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."
The price is CA $148
CA $281 total
includes taxes & fees
Aug 25 - Aug 26
Master qtr close to nature & easy urban facilities
The Randolph Hotel Room 206
Bar (on property)

The Randolph Hotel Room 206

The price is CA $73
CA $225 total
includes taxes & fees
Aug 24 - Aug 25
The Randolph Hotel Room 206
The Tailor House
Exterior

The Tailor House

10.0 out of 10, Exceptional, (42)
"A relaxing well appointed home with easy walking distance to downtown Woodstock!"
The price is CA $201
CA $407 total
includes taxes & fees
Aug 25 - Aug 26
The Tailor House
Cozy Gated Home Walk to Navy Base and Parks
Fridge, microwave, oven, stovetop

Cozy Gated Home Walk to Navy Base and Parks

The price is CA $134
CA $804 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Gated Home Walk to Navy Base and Parks
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 "
The price is CA $379
CA $453 total
includes taxes & fees
Aug 21 - Aug 22
Spacious Ranch blocks away from downtown McHenry
Cozy Outdoor Space + BBQ | LCP Collection
Exterior

Cozy Outdoor Space + BBQ | LCP Collection

9.0 out of 10, Wonderful, (2)
"Good"
The price is CA $428
CA $938 total
includes taxes & fees
Sep 17 - Sep 18
Cozy Outdoor Space + BBQ | LCP Collection
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, (14)
"Comfortable and pleasant view of the lake"
The price is CA $373
CA $610 total
includes taxes & fees
Aug 25 - Aug 26
This is a VACATION spot with a million dollar view!
Modern Farmhouse | Yard + Pets OK | LCP Collection
Fridge, microwave, oven, stovetop

Modern Farmhouse | Yard + Pets OK | LCP Collection

The price is CA $288
CA $724 total
includes taxes & fees
Sep 16 - Sep 17
Modern Farmhouse | Yard + Pets OK | LCP Collection
Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (15)
"The house, yard and location were all perfect. "
The price is CA $409
CA $744 total
includes taxes & fees
Aug 25 - Aug 26
Charming 3-bedroom house in Grayslake
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Property grounds

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

10.0 out of 10, Exceptional, (1)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
The price is CA $328
CA $712 total
includes taxes & fees
Aug 24 - Aug 25
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Relaxing Lake Zurich 3BR + Patio | LCP Collection
Fridge, microwave, oven, stovetop

Relaxing Lake Zurich 3BR + Patio | LCP Collection

8.0 out of 10, Very good, (4)
"Property was newly updated, was in a great location for us and met our needs. We had an issue with heating and owner resolved it. There were a few details that needed attended to, I discussed with owner and am confident that he was listening. Harry is very responsive. We would stay here again."
The price is CA $324
CA $761 total
includes taxes & fees
Sep 8 - Sep 9
Relaxing Lake Zurich 3BR + Patio | LCP Collection
Relax and recharge! Charming lake view house in quaint Wonder Lake, IL!
Fridge, microwave, oven, stovetop

Relax and recharge! Charming lake view house in quaint Wonder Lake, IL!

The price is CA $312
CA $630 total
includes taxes & fees
Aug 27 - Aug 28
Relax and recharge! Charming lake view house in quaint Wonder Lake, IL!
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
Fridge, microwave, oven, stovetop

Near Lake 4BR w/ Hot Tub & Games | LCP Collection

10.0 out of 10, Exceptional, (13)
"This house had everything we needed and could have wanted! We had a wonderful stay. "
The price is CA $508
CA $999 total
includes taxes & fees
Sep 7 - Sep 8
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Paper towels, dining tables

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

The price is CA $250
CA $566 total
includes taxes & fees
Aug 27 - Aug 28
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
The Main Event Game House on the Huntley Square!
Interior

The Main Event Game House on the Huntley Square!

9.8 out of 10, Exceptional, (15)
"Beautiful, accommodating, activities for all ages"
The price is CA $176
CA $403 total
includes taxes & fees
Sep 2 - Sep 3
The Main Event Game House on the Huntley Square!
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

Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

10/10 Excellent
"We found the hotel to be clean and quiet and the room was very nice. The staff was attentive and friendly. We will definitely there again next time we are in Chicago."
Larry 2-night trip
Posted 2 days ago
Holiday Inn Chicago - Schaumburg by IHG