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Compare 244 Vacation Homes in Highwood with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (21)
"The property was perfect for me and my buddies for a football weekend!"
Great 3 bedroom rental unit near Logan Square
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Room

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

9.4 out of 10, Exceptional, (17)
"Very clean"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
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, (19)
"Great location for needing to be around the north park area, my grandmother easily maneuvered (87 y/o), and our 4 y/o loved watching TV on the projector. Easy parking, easy access to downtown. If you need to be in the area I’d definitely recommend staying here!"
Chicago Riverhouse with private fenced in oasis
Lake/Beach Getaway (Remodeled)
Children's area

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (28)
"excellent location - very clean - close to everything we wanted to visit - owners very helpful only 20 min from Antioch where we had our family reunion - this is the 2nd year we have stayed here - very happy - lake visable from front windows - beds comfy - kitchen completely stocked - great sunsets - easy walking in the area - shopping close by wonderful rental"
The price is SAR 751
SAR 1,228 total
includes taxes & fees
28 Jan - 29 January 2025
Lake/Beach Getaway (Remodeled)
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, (32)
"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
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, (17)
"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
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Living area

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
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

9.2 out of 10, Wonderful, (7)
"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
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, (120)
"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!
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!
Comfy King bed, Free Wi-Fi, Home in Des Plaines

Comfy King bed, Free Wi-Fi, Home in Des Plaines

10.0 out of 10, Exceptional, (3)
"This home was tidy and beautiful. It fit all of us so perfectly and we were able to spend quality time together with our sailor!! We had no problems with this property and the manager was very responsive! Thank you so much!"
The price is SAR 671
SAR 1,899 total
includes taxes & fees
5 Jan - 6 January 2025
Comfy King bed, Free Wi-Fi, Home in Des Plaines
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Interior

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

9.8 out of 10, Exceptional, (7)
"Overall listing was spot on. Clean overall, a little on the chilly side upon arrival and one trash can was not empty. Couple items it could use are hand towels for rhe bathrooms, additional dish towels and dish cloths in the kitchen. Aybe add some board games? Other then a few additionas it was a great locations and perfect for what we needed. "
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants
Interior

Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants

9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed our stay at this property. Very clean, with all the conveniences you would need. Great location...nice neighborhood with easily accessible stores, restaurants, etc all within reasonably short driving distances. Would absolutely recommend staying here!"
Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants
IVP Manor House Close to Lake Beach & Naval Base
Living room & Eat in Kitchen

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
Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston
Exterior

Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston

2.0 star property
10.0 out of 10, Exceptional, (1)
"Good place to hang out with friends."
The price is SAR 1,757
SAR 3,255 total
includes taxes & fees
8 Jan - 9 January 2025
Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston
Cozy Wauk-Townhse near navy base
Living area

Cozy Wauk-Townhse near navy base

2.0 star property
10.0 out of 10, Exceptional, (1)
"The neighborhood is quiet and well established. You are close to many places, especially the Naval base. The water gets hot quickly. Plenty of towels and blankets. Just needs more sitting room in living area. I would definitely stay again. Greats snacks too. e to many places, especially to Great Lakes base."
Cozy Wauk-Townhse near navy base
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
Interior

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great house! Great stay! Thanks!"
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
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!"
Quaint Bungalow, near Great Lakes Naval Base
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
Living room

100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!

10.0 out of 10, Exceptional, (15)
"Nice stay and good location."
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
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

Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking
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, (120)
"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!
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
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.