Photo by Joe Farmer

Search Vacation Homes in Highland

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 213 Vacation Homes in Highland with updated reviews, rates, and availability.

Spacious 3br home near Chicago, fenced yard for pets
Exterior

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (3)
"GREAT"
The price is SAR 450
SAR 1,148 total
includes taxes & fees
17 Feb - 18 Feb
Spacious 3br home near Chicago, fenced yard for pets
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Exterior

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Cheerful 4 bedroom smart home w/ indoor fireplace
Room

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Living area

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Nestled just behind Marquette Park. 5 minute walk to beach.
Interior

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Exterior

Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.

10.0 out of 10, Exceptional, (17)
"Property was nice"
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Full Luxurious Modern House Near Chicago
Living area

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
Exterior of the Greystone

Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking

6.4 out of 10, (5)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Beautiful Modern Historic Greystone - Near Lake Michigan- Free Parking
Dreamsville Gateway to Indiana Dunes National Park
Private kitchen

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (57)
"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (18)
"It felt like home. Didnt want to leave."
Cozy Home Sweet Homewood.
Woodlawn Oasis...10 Minutes to Dining & Downtown
Living area

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
Living area

Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

9.4 out of 10, Exceptional, (10)
"The home is nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now
Lux Home in Chicago 7mins Downtown
1st Floor Living Room

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown
Spacious 4-bedroom house in superb Chicago with WiFi, AC
Living area

Spacious 4-bedroom house in superb Chicago with WiFi, AC

Spacious 4-bedroom house in superb Chicago with WiFi, AC
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
18 foot round above ground pool with lockable pool gate.

Rare Private Heated Pool w/in 1.5 Blocks to the Beach!

9.8 out of 10, Exceptional, (81)
"Property was as advertised. Location was great. We were in the pool or at the beach. Great for family or couples. Plenty of room. The deck is not attached to the house, so a lot of stairs involved. Inside does not flow into outside."
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Living area

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

6.0 out of 10, (1)
The price is SAR 319
SAR 991 total
includes taxes & fees
17 Feb - 18 Feb
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Miller Beach Blue Door By The Shore #2
Room

Miller Beach Blue Door By The Shore #2

10.0 out of 10, Exceptional, (4)
"I had a very nice stay the property was very clean. I loved the location probably would’ve been better if I had rented in the summer because it was a little chilly in the home but otherwise everything was great. "
Miller Beach Blue Door By The Shore #2
University of Chicago Condo-Upgraded and Spacious w/Parking
Spacious living area

University of Chicago Condo-Upgraded and Spacious w/Parking

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here. The apartment is very spacious and is just delightful. Attention was clearly made to decorating. Having two full bathrooms is definitely a plus. Neighborhood is nice and having your own parking space is so helpful. We chose this location because it is close to the Griffin Museum of Science & Industry. We recommend this place to anyone. "
University of Chicago Condo-Upgraded and Spacious w/Parking
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.
Don't see what you're looking for?
See all available properties in Highland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Highland

Spacious 3br home near Chicago, fenced yard for pets
Exterior

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (3)
"GREAT"
The price is SAR 450
SAR 1,148 total
includes taxes & fees
17 Feb - 18 Feb
Spacious 3br home near Chicago, fenced yard for pets
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
forrestville home

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.6 out of 10, Exceptional, (69)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
Interior

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
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.