Photo by Meghan hernandez

Holiday Rentals in Highland Park

  • 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

Holiday Rentals in Highland Park

Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (282)
"Will stay again."
The price is €209
includes taxes & fees
13 Jan - 14 Jan
Level Chicago – Old Town
Walking distance to restaurants, shops and Lake Michigan,
Exterior

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,
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
Ground Floor Studios in Chicago by 747 Lofts
Stay in “STYLE” Apartment, close to CHI downtown
Fridge, microwave, oven, dishwasher

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (72)
"This is the 3rd time I’ve booked this Ukrainian Village apartment. It’s comfortable and has everything needed for visits into the city. "
Stay in “STYLE” Apartment, close to CHI downtown
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (84)
"Very close to the train. Good location "
Stunning 3 BR in prime Chicago location
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (153)
"We had a great stay, location was great, very clean, beautifully remodeled, the bathroom felt like a 5 star hotel with all the upgrades they've done. The first night the refrigerator stopped working, they immediately went over to try to fix it but were unsuccessful, they offered to purchase ice for us and by the next day they had purchased and installed a new refrigerator. Overall, we had a great experience and would definitely stay here again. "
NEW LUXURY CONDO WITH PATIO DECK
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Terrace/patio

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (83)
"This property worked well for our group of 14. The need to go outside to get between the upper and lower levels had been made very clear. It was a bit tricky at first with 5 young children, but we all adjusted pretty quickly. The lower level is more basic than upstairs but still worked very well for 5 of the group. The neighborhood was perfect for the location of the wedding we were attending, and having garage parking was fantastic. Definitely recommend."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Exterior

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
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Fridge, microwave, oven, stovetop

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
Hidden East Village Gem
Terrace/patio

Hidden East Village Gem

9.6 out of 10, Exceptional, (31)
"The inside space was very good. The outside construction noise was almost unbearably. The neighbor upstairs was very loud. "
Hidden East Village Gem
Quaint Bungalow, near Great Lakes Naval Base
TV, books

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 €306
includes taxes & fees
4 Feb - 5 Feb
Quaint Bungalow, near Great Lakes Naval Base
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Fridge, microwave, oven, stovetop

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Interior

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!
Stunning / Spacious 6BD Home + garage - Bucktown!
Fridge, microwave, oven, stovetop

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Property grounds

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

10.0 out of 10, Exceptional, (39)
"So clean and welcoming with a terrific location just steps from a lovely beach! The property was very clean, comfortable and well-kept, and looked like the kitchen and bathrooms had been recently re-done (loved the tile and fixtures!). The shower in the master is a spa-like experience! Great communication with the owner, too. So happy with our stay, and we would absolutely look forward to saying here again!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel cot

Bright Garden Studio

8.8 out of 10, Excellent, (16)
"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...
The price is €208
includes taxes & fees
9 Jan - 10 Jan
Bright Garden Studio
Game room+King Bed+WiFi+Near Chicago & O’Hare
Fridge, microwave, oven, stovetop

Game room+King Bed+WiFi+Near Chicago & O’Hare

10.0 out of 10, Exceptional, (22)
"We had 5 people stay. 3 bedrooms and the two couches that fold out into beds. We hung out on the deck each night, but never ended up using the fire pit. Was a warm night anyway. Great stay. "
The price is €415
includes taxes & fees
13 Jan - 14 Jan
Game room+King Bed+WiFi+Near Chicago & O’Hare
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (195)
"The apartment is beautifully decorated and updated. Ross, the host gave us a welcome tour and everything was clearly explained. Beds are comfortable and rooms are spacious. We were relieved our rental minivan (just barely) fit in the garage! We did the kitchen wasn't as well equipped as we would have liked, but we were cooking a Thanksgiving meal which may have been a bit ambitious. The meal turned out well and we enjoyed our stay immensely!"
Walking distance to restaurants, shops and Lake Michigan,
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile
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 Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Highland Park you may be interested in

Claridge House
Lobby

Claridge House

4.0 star property
8.6 out of 10, Excellent, (1220)
"LOVELY STAY FOR THE MARATHON. LOVE THE COLD WATER NEAR RECEPTION. "
The price is €125
includes taxes & fees
13 Jan - 14 Jan
Claridge House
Thompson Chicago, by Hyatt
2 bars/lounges

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1049)
"Loved the hotel, but they should have told us in advance that one of the two elevators was out of service. That made the stay less enjoyable. "
The price is €128
includes taxes & fees
27 Jan - 28 Jan
Thompson Chicago, by Hyatt
Chicago Getaway Hostel
Terrace/patio

Chicago Getaway Hostel

2.0 star property
8.8 out of 10, Excellent, (1007)
"Worth the money! This property is in a great location to see a non-tourist experience of Chicago! The bathrooms were not the best, but my room was clean. Overall, worth the price! "
The price is €64
includes taxes & fees
16 Jan - 17 Jan
Chicago Getaway Hostel
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.

Frequently asked questions

Are there holiday rentals in Highland Park?

Yes, there are holiday rentals close to the most popular sights in Highland Park, or you can select a more secluded option if you're looking for a relaxing stay. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What are some of the best holiday rentals that Highland Park has to offer?

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!: This holiday home rental outside of Highland Park is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Highland Park?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Cultural attractions include Ravinia Park and Ravinia Pavilion, whereas Chicago Botanic Garden and Lake Michigan are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.