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Compare 243 Vacation Homes in Highwood with updated reviews, rates, and availability.

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.4 out of 10, Exceptional, (21)
"This was my first booking with VRBO, we were in Chicago for my niece's Navy graduation. Sam, the host, was extremely communicative. I had sent him a question in the inbox and he called me within 3 minutes. The property is spacious, only 4 minutes from base and very close to a multitude of restaurants. Very clean, kitchen was not lacking in glasses / plates / accessories. We had a wonderful stay and I highly recommend Sam's house. Thank you again, Sam!!"
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Your Next Vacation Home

9.8 out of 10, Exceptional, (31)
"It was great! close to a lot. "
The price is AED 551
AED 1,031 total
includes taxes & fees
2 Mar - 3 Mar
Your Next Vacation Home

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (48)
"This home was clean, comfortable, spacious and inviting. Michael met us to provide key and a review of all the home offered. Spacious pantry and kitchen had everything we needed for entertaining. The large dining table and comfy couches were perfect for enjoying the football game Everone complimented the home’s beauty and lovely backyard setting. Would highly recommend and we will be back. Thank you!"
Breathtaking home close to Schaumburg, Chicago

IVP Manor House Close to Lake Beach & Naval Base

9.6 out of 10, Exceptional, (51)
"We needed a good centralized location for Thanksgiving with our relatives. This house was the perfect location, was very spacious, very clean, and comfortable beds and pillows. Would definitely stay again, thank you for your hospitality! "
IVP Manor House Close to Lake Beach & Naval Base

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (47)
"This place was amazing!! The bed was super comfortable and the jet tub was out of this world!! It was very clean and quiet. The host was very accomodating and had great communication. My husband and stayed overnight because he had an army function to attend. This was perfects! to attend. "
The price is AED 400
AED 727 total
includes taxes & fees
24 Feb - 25 Feb
Master qtr close to nature & easy urban facilities

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Roxan Corner

8.4 out of 10, Very Good, (31)
"We were very pleased with the location of the home. The property seemed to be well maintained and accomodating. The only downfall was that it seemed very pricey for the time of year"
Roxan Corner

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (21)
"This property was perfect for several family members to stay & be comfortable, especially with having their own bathroom. It was very clean & spacious. It is a unique & awesome property. I was in touch with the host. She was delightful & quick to reply. The neighborhood is very nice. The location was perfect to get to the base & close to the cute town of Libertyville. I would definitely stay here again! "
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (5)
"We stayed here when our daughter graduated from the Navy. House is as described and sticked/furnished with all you need or would expect. House was clean. Neighborhood seemed a little "sketchy" but we had zero issues or concerns while we were there. If you are coming for a Navy graduation location is good. Less than 10 mintues to base except on graduatiin morning. Traffic is horrendous but were still able to get from home and in our seats in less than 90 minutes. Would recommend and stay again"
Family frndly TwnHm by navy base

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.4 out of 10, Exceptional, (8)
"Excellent home, plenty of room, very clean."
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (38)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (123)
"Spacious inside, 9 bedrooms, very warm in a cold month. Good location to walk, close to public transit and ample parking - squeezed in 5 vehicles. Owner contact and responses excellent."
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is AED 496
AED 1,131 total
includes taxes & fees
23 Feb - 24 Feb
Quaint Bungalow, near Great Lakes Naval Base

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Adorable 2-bedroom home near downtown Grayslake!

10.0 out of 10, Exceptional, (22)
"Cute and cozy. Very clean. Hosted a successful Thanksgiving dinner with local family. Had everything we needed (we didn't cook a turkey, though). Also spent quality time with our Navy boot camp graduate! Great house!"
Adorable 2-bedroom home near downtown Grayslake!

Entire Lake Villa Home!

9.4 out of 10, Exceptional, (37)
"We stayed over the weekend to attend family events. The location is very near where we needed it to be. If you are here to go to Six Flags or Great Lakes Naval Base. You should be good as it’s about 20 minutes out. Quiet neighborhood"
Entire Lake Villa Home!

2bed /1bath TH - 7min Six Flags, 14min Navy Base

10.0 out of 10, Exceptional, (4)
"The listing online was very accurate to what we arrived. And experienced everything we needed was pretty much on hand easily.The best accommodations I could have asked for"
The price is AED 441
AED 1,027 total
includes taxes & fees
22 Feb - 23 Feb
2bed /1bath TH - 7min Six Flags, 14min Navy Base

PROMO 10% WEEKLY AND 15% MONTHLY Near Northwestern, Beaches Parking Fenced Yard

9.8 out of 10, Exceptional, (6)
"Good "
The price is AED 702
AED 1,626 total
includes taxes & fees
23 Feb - 24 Feb
PROMO 10% WEEKLY AND 15% MONTHLY Near Northwestern, Beaches Parking Fenced Yard
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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Other property types in Highwood

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (90)
"Nice and quiet neighborhood close to everywhere we needed. Jamie was easy to talk to and down to earth, the unit was clean and exactly what we expected. Jamie was approachable and easily available if we felt we had questions or needed suggestions. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
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.