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
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

Compare 253 Vacation Homes in Highland with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.
Miller Beach Blue Door By The Shore #2
Interior

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
Private Home Awaits
Fridge, microwave, oven, stovetop

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
Private Home Awaits
House with garage, outdoor dining and basement bar
Fridge, microwave, oven, dishwasher

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Smart TV, fireplace, books, offices

Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

10.0 out of 10, Exceptional, (33)
"Our stay was nothing short of amazing! The host was incredibly responsive and flexible, allowing us to make a last-minute change to our reservation. She went above & beyond to be accommodating, which made it possible for our family to still gather for a special Christmas and New Year celebration. The house itself was full of character, with unique artwork and quirky touches that made it feel like a fun, creative retreat. The serene location, surrounded by nature, provided the perfect backdrop...
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Casa Blanca in Miller Beach!
Exterior

Casa Blanca in Miller Beach!

9.8 out of 10, Exceptional, (69)
"8 of us stayed at the house, plenty of beds, plenty of places to sit and talk / watch TV, kitchen had everything we needed. Highly recommend"
Casa Blanca in Miller Beach!
Restored Cottage Across The Street From The Beach!
Terrace/patio

Restored Cottage Across The Street From The Beach!

9.8 out of 10, Exceptional, (95)
"Great house for large family. Very cozy, yet spacious. Fenced yard was great as was the close proximity to the beach"
Restored Cottage Across The Street From The Beach!
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

10.0 out of 10, Exceptional, (1)
"Lovely new (or well remodeled?) house in a nice neighborhood. Host was nice and communicative. Kitchen is well stocked. There’s only one shower but we had no problem sharing. "
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC
Chic & Stylish 3-bedroom house in Palos Heights
Private kitchen

Chic & Stylish 3-bedroom house in Palos Heights

8.0 out of 10, Very Good, (1)
"We enjoyed our stay at this vrbo property - it was very conveniently located as we were visiting family in the Palos Heights area and there are grocery stores and other shopping and restaurants within a few minutes drive. The property was clean and had most basic conveniences like shampoo, conditioner, dish soap, and detergent. The only surprise was that there was another group staying in the basement (with a separate entrance) which wasn't mentioned at all in the property description. "
Chic & Stylish 3-bedroom house in Palos Heights
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (7)
"Two grandmas, a mom and a daughter came to experience open house for The University of Chicago. This home was so nice as it was a close and safe walk to campus. We all had an extremely comfortable bedroom as well as our own bathroom. The neighborhood felt safe and had beautiful buildings to admire while we walked. We never felt like we lacked for anything. "
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Steps to Lake Michigan Beach: Gary Vacation Rental
Fridge, microwave, stovetop, dishwasher

Steps to Lake Michigan Beach: Gary Vacation Rental

9.2 out of 10, Wonderful, (34)
"Nice"
Steps to Lake Michigan Beach: Gary Vacation Rental
Spacious Family Glenwood Estates Home w/ Hot Tub!
Indoor spa tub

Spacious Family Glenwood Estates Home w/ Hot Tub!

9.4 out of 10, Exceptional, (14)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!
Pet-Friendly Lake Getaway: 1 Block to Beach!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Lake Getaway: 1 Block to Beach!

10.0 out of 10, Exceptional, (34)
"Property was very clean and photos accurate. Check in process was easy and we enjoyed a quick fall weekend get away to hike the Dunes. Good communication from owner. Thanks!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (21)
"Nice sice fenced in yard. Dog park within a short walk. Nice smaller home with 3 good size bedrooms. Kitchen was convenient for cooking meals."
Beautiful and updated place to stay in a quiet neighborhood of Munster Indiana.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Terrace/patio

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (34)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Lux Home in Chicago 7mins Downtown
Fridge, microwave, oven, stovetop

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
Modern Historic Greystone - Near Lake - Free Prkg
Fridge, microwave, oven, stovetop

Modern Historic Greystone - Near Lake - Free Prkg

6.4 out of 10, (5)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Fridge, microwave, stovetop, dishwasher

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
Dreamsville Gateway to Indiana Dunes National Park
Exterior

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
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

Comfort Inn Chicago Wind Creek Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
3.8 out of 10, (16)
"The staff was polite and friendly! I didn't care that they were apparently under construction and I didn't are much for that "
The price is SAR 335
SAR 379 total
includes taxes & fees
12 Apr - 13 Apr
Comfort Inn Chicago Wind Creek Casino
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

10.0 out of 10, Exceptional, (16)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.
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.