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Compare 239 Vacation Homes in Highwood with updated reviews, rates, and availability.

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
First floor living room with leather couch, smart cable TV, and Alexa speaker.

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

10.0 out of 10, Exceptional, (121)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Private kitchen

3-bedroom house WiFi in lovely Waukegan Near Gurnee

2.0 star property
4.6 out of 10, (12)
"Cute little house at all the necessities convenient to Naval base where we spent most of our time"
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Quaint Bungalow, near Great Lakes Naval Base
Welcome to our guest house, "A Little House on Prairie"!

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 1,139 total
includes taxes & fees
4 Feb - 5 Feb
Quaint Bungalow, near Great Lakes Naval Base
Your Next Vacation Home
Dining

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"This is the second year we have stayed at this location during Thanksgiving. It is convenient for visiting family members in Park Ridge and Glenview. The four bedrooms and two bathrooms provide the space we need. There is also a well equipped kitchen. "
The price is AED 551
AED 1,046 total
includes taxes & fees
28 Jan - 29 Jan
Your Next Vacation Home
Breathtaking home close to Schaumburg, Chicago
Exterior

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (46)
"We had unexpected changes last minute for Thanksgiving and our Host was so great and accommodating. The space was roomy and beautiful with the rooms flowing into each other so little groups of people could talk and nosh and enjoy the food and company. The light coming in from the windows and the backyard is a little piece of nature to enjoy. At our request, our wonderful host even snuck in to start a fire for us in the firepit, making it even more homey. My husband, myself, my sister, and my...
Breathtaking home close to Schaumburg, Chicago
Cheery 2+bedroom home with free parking on premises
Living area

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend."
Cheery 2+bedroom home with free parking on premises
Chicago Riverhouse with private fenced in oasis
Escape to your private outdoor oasis, available May-October. Lounge on the illuminating sofa, sway in the hammock, gather around the table for 8, fire up the grill – all within the serenity of a fenced-in retreat

Chicago Riverhouse with private fenced in oasis

9.8 out of 10, Exceptional, (20)
"Second time staying at the Riverhouse. Loved it just as much as the first time.The location is terrific...in the city, but plenty of parking. Local mom and pop restaurantaway.walkable."
Chicago Riverhouse with private fenced in oasis
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Libertyville Vacation Rental | 3BR | 3BA | 2,700 Sq Ft | Step-Free Access

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (18)
"We rented this house to stay for my daughter’s graduation from Navy Boot Camp. It was an easy drive in and ample room for everyone. The host was awesome and attentive to our needs. Honestly, we didn’t really have any needs, but we used party poppers in the house and wanted to be able to clean them up, but we couldn’t find the broom. Being from California, I was super nervous about being cold, but as soon as we walked in the house, it was super warm and felt so cozy. The heated floors are...
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Eddy House, Roscoe Village Hideaway
Living area

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
Exterior

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

9.4 out of 10, Exceptional, (8)
"We had a mini cousin reunion with family who drove in from different states. No one here has a house big enough to have all of us, so this was the perfect option. The house was lovely, neighborhood very nice, easy to get to, and the host was gracious making us feel like we were all at home. I’d give it 10/5 stars if I could!"
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
Roxan Corner
Room

Roxan Corner

8.4 out of 10, Very Good, (30)
"Came to see my son graduate bootcamp"
Roxan Corner
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Interior

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

10.0 out of 10, Exceptional, (23)
"My family gets together every fall. Our first stay in a vacation rental home was in 2015. It is with almost ten years of knowledge that I declare this house one of the best. We had an amazing stay! Craig is wonderful host. This house is filled with all sorts of extras and bonuses. Getting in the house was easy. I can't tell you how many times we stood outside of a house because the code didn't work. We walked through the house oohing and ahhing in each room. Everyone loved watching movies...
The price is AED 2,079
AED 3,190 total
includes taxes & fees
27 Jan - 28 Jan
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
Living area

Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!

10.0 out of 10, Exceptional, (11)
"It was a great house with needed amenities and lots of space. Great location not far from downtown. Host was great to communicate with."
Elegant 3BD Chalet! 🌲15min to ORD/Train 2 Dwntwn!
The Greenleaf House—Whole House
Living area

The Greenleaf House—Whole House

9.8 out of 10, Exceptional, (27)
"The house was big enough for whole family. It was also in a great location. However, the locked bedroom doors were a big inconvenience and the carpeting was disgusting. So dirty. Did not like walking in it without shoes."
The Greenleaf House—Whole House
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Living area

Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills

9.8 out of 10, Exceptional, (10)
"It was a quiet and cozy home near Great Lakes RTC. Great location. "
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Master qtr close to nature & easy urban facilities
Exterior

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (44)
"Great location.Description was on point.Accommodations were a bet. "
The price is AED 400
AED 713 total
includes taxes & fees
13 Jan - 14 Jan
Master qtr close to nature & easy urban facilities
Massive 4BR, 4-level 3,300 sq ft House, WiFi + Pool Table
Spacious front yard with scenic views, ideal for relaxation and outdoor

Massive 4BR, 4-level 3,300 sq ft House, WiFi + Pool Table

10.0 out of 10, Exceptional, (1)
"Relaxing "
The price is AED 624
AED 1,738 total
includes taxes & fees
12 Jan - 13 Jan
Massive 4BR, 4-level 3,300 sq ft House, WiFi + Pool Table
Family frndly TwnHm by navy base
Living area

Family frndly TwnHm by navy base

2.0 star property
10.0 out of 10, Exceptional, (3)
"We stayed here for my son’s graduation from RTC Great Lakes. Very convenient and close to the base. House was very clean, comfortable, nicely decorated and well stocked with everything we needed for a comfortable weekend with our new Sailor. Jesse was an excellent host, very quick to respond to messages and very accommodating. One of the nights we stayed there was a snow storm and first thing in the morning he was there to shovel the walkways and driveway for us! I would highly recommend staying...
Family frndly TwnHm by navy base
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
Exterior

Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house! Great stay! Thanks!"
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Living area

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

10.0 out of 10, Exceptional, (73)
"Overall the stay was absolutely wonderful! Couldn't give complete 5 stars only due to the listing mentioned a waffle maker that we couldn't find but we were VERY happy to find an Air fryer on the property. The owner does an amazing job of explaining the rules of the property in the binder close to the door. The space was super cozy with a fireplace and a big enough kitchen to allow everyone o cook together if that's something you like to do. The property parking was first come first serve and...
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
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

Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Private kitchen

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

10.0 out of 10, Exceptional, (166)
"Fantastic location and an outstanding host! I had an amazing stay. The space was ideal for my needs, offering a comfortable and convenient setting to assist my daughter with her wedding preparations. It had everything I was looking for—well-equipped with great amenities and in a prime location. The property was spotless, peaceful, and provided everything needed for a smooth and enjoyable experience. Easy street parking was always available! I highly recommend this place to anyone looking for a...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Quaint Bungalow, near Great Lakes Naval Base
Welcome to our guest house, "A Little House on Prairie"!

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 1,139 total
includes taxes & fees
4 Feb - 5 Feb
Quaint Bungalow, near Great Lakes Naval Base
Your Next Vacation Home
Dining

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"This is the second year we have stayed at this location during Thanksgiving. It is convenient for visiting family members in Park Ridge and Glenview. The four bedrooms and two bathrooms provide the space we need. There is also a well equipped kitchen. "
The price is AED 551
AED 1,046 total
includes taxes & fees
28 Jan - 29 Jan
Your Next Vacation Home
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.