Prospect Heights Holiday Rentals

    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 Prospect Heights

Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (83)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is NZ$193
per night
27 May - 28 May
Sonder Market Hall
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is NZ$395
per night
27 May - 28 May
Level Chicago – Old Town
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is NZ$156
per night
30 May - 31 May
WoodSpring Suites Chicago Addison
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is NZ$316
per night
27 May - 28 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (21)
"We were in town for our son’s wedding and this was the perfect location for our group. Apartment was as advertised and the host was very responsive and helpful. The rooftop provided a perfect place for some pre-wedding groom/best man photos as well."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is NZ$566
per night
30 May - 31 May
national historic home near downtown airports no parties no events
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, (18)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"Great stay! All of the rooms were wonderful! Really close to food! There are a lot of stairs so make sure you are able to walk up but really great place!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is NZ$253
per night
27 May - 28 May
Ground Floor Studios in Chicago by 747 Lofts
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is NZ$511
per night
28 May - 29 May
LUXE 3 BR, 2 BA + Hot Tub
Fridge, microwave, oven, dishwasher
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (61)
"We booked this apartment for a quick trip and it is just as pictured. They had so many little extras in the bathroom, just in case you forgot something! I felt horrible for the tenant under due to our heavy footed children!"
Stay in “STYLE” Apartment, close to CHI downtown
Fridge, microwave, oven, stovetop
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, (125)
"This was our second time booking and our experience was as great as the first time. It is a convenient location to many areas around Ukraine Village. Love the space and immaculate condo. As a suggestion if you enjoy cooking bring your own spices and oil. They have everything in reference to dish ware, knives, pots/pans and glasses/cups. It was my birthday weekend and the host had a special gift for me. Very thoughtful!"
NEW LUXURY CONDO WITH PATIO DECK
Don't see what you're looking for?
See all available properties in Prospect Heights
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.

Other types of properties in Prospect Heights you may be interested in

Lobby sitting area
Hotel Felix River North/Magnificent Mile
4.0 star property
8.0 out of 10, Very good, (1012)
"Close to the Riverwalk, liked the design and decor, good atmosphere. "
The price is NZ$235
per night
27 May - 28 May
Hotel Felix River North/Magnificent Mile
Bar (on property)
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.0 out of 10, Very good, (3404)
"It was a great location to Michigan Ave!!"
The price is NZ$279
per night
28 May - 29 May
The Whitehall Hotel, BW Premier Collection
Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, (1842)
"Very Good breakfast with waffles, scrambled eggs, potatoes, corned beef hash, yogurt, juices, cereals. Bed very comfortable. Good Fitness Room with treadmills, multi-station weight machine, yoga mats. Drawbacks: restaurants are not walkable (Hitachi across the street was closed at 8 pm), waited for 55 minutes for complimentary shuttle."
The price is NZ$173
per night
26 May - 27 May
Best Western At O'Hare
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Prospect Heights holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Prospect Heights. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Prospect Heights. Seeing all the best attractions is bound to make you fall in love with Prospect Heights. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Prospect Heights short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Prospect Heights?

Yes, there are holiday rentals close to the most popular sights in Prospect Heights, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Prospect Heights has a good selection of restaurants. Make sure you have time to check out the lake views and shopping during your trip.

What are some of the best holiday rentals that Prospect Heights has to offer?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This holiday home rental outside Prospect Heights is located in the city centre, and offers a BBQ, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Prospect Heights?

While exploring the area, visit family-friendly sights like Northbrook Sports Complex, or get outside and enjoy nature at Isaak Walton Park. You’ll find favourite places to visit such as Naval Base Great Lakes and Wrigley Field in the wider area.

What are holiday rentals like in Prospect Heights?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Prospect Heights. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.

Recent reviews of Prospect Heights properties
Expedia verified reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

5/5 Excellent
"Great hotel."
A verified traveller stayed at Hotel Felix River North/Magnificent Mile
Posted 18 hours ago
Hotel Felix River North/Magnificent Mile