Photo by Jeff Hancock

Holiday Homes in Plainfield

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Featured Holiday Homes in Plainfield

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (71)
"Plenty of space. Great location. We enjoyed our stay very much. My only suggestion would be go in the day before guest check in and make sure everything smells and looks clean. "
Furnished Private home in Aurora sleeps 9 guests

Spacious Deck & Balcony, Game Area, Garage

10.0 out of 10, Exceptional, (3)
"It was amazing staying here "
The price is AU$779
includes taxes & fees
26 Nov - 27 Nov
Spacious Deck & Balcony, Game Area, Garage

Charming 3-bedroom house just minutes from Downtown Wheaton!

Charming 3-bedroom house just minutes from Downtown Wheaton!

King Bed, DIsney+, Spacious, Family-Friendly House

10.0 out of 10, Exceptional, (20)
"I really enjoyed our stay at this location. It had good appliances and was very clean. Owners made it a point to communicate throughout! "
The price is AU$583
includes taxes & fees
2 Dec - 3 Dec
King Bed, DIsney+, Spacious, Family-Friendly House

Desirable chic home in a Prime Location!

9.0 out of 10, Wonderful, (2)
"My coworker and I stayed at this property for a work trip. The house was clean and modern, provided a bathroom for each of us, and was within walking distance of our company office in parkview plaza."
Desirable chic home in a Prime Location!

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

10.0 out of 10, Exceptional, (11)
"We used the space to throw my friend a birthday party. The house was as described and we had a great time. Veronica answered all of our questions and was quick to respond. I would definitely recommend this place to others. "
The price is AU$1,296
includes taxes & fees
2 Dec - 3 Dec
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Clarendon Hills Top Floor

6.6 out of 10, (4)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (15)
"Older property which matched description well. Comfortably fit 5 adults and teens for 4 night stay. Quiet neighborhood even though it is right next to highway. Grocery store within a few mins. We traveled several times to downtown Chicago and Rosemont without issues (other than normal chicago traffic). There are stairs from any entrance, so just be prepared if you have a heavy cooler like we did. :) Could have been a bit cleaner, but that would not stop me from staying again. The host...
The price is AU$709
includes taxes & fees
2 Dec - 3 Dec
LUXE 3 BR, 2 BA + Hot Tub

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (162)
"Very clean and well maintained. Would stay again for sure. "
Historic home with easy access to Chicago

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (48)
"Our family of 4 had a wonderful stay here! Great neighborhood and a spacious home! The beds were super comfy & the home was decorated nicely! Thank you for having us Amanda! We’ll be back :) "
Spacious open concept home w/ game room + firepit

Discover Wheaton's charm.

9.8 out of 10, Exceptional, (8)
"An exceptional place to stay. We felt very welcome. Plenty of room both indoors and out. Host is very responsive, respectful, and accommodating!"
Discover Wheaton's charm.

Spanish style home with in-ground pool

9.8 out of 10, Exceptional, (36)
"This home is rated in my top 3 all time favorite vacation homes. I travel a LOT. This beauty was emaculate. Owners amazing! Excellent communication. Check-in, check out THE best. Run don't walk to book this fabulous renter!"
Spanish style home with in-ground pool

Cozy 5-bedroom with lake views and spacious deck

10.0 out of 10, Exceptional, (8)
"This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area."
Cozy 5-bedroom with lake views and spacious deck

Luxury Suite in Glen Ellyn, IL USA

10.0 out of 10, Exceptional, (5)
"The host was very communicative from the beginning. Had a bit of a booking hiccup via another site. Reached out to the host and she responded and rectified the situation right away. The unit is a split level, accessible only through the garage. We received the code to enter the door to the unit, well in advance. However, we did not receive the code to enter the garage until arrival (and after having to reach out to the host). Once again, the host was very quick to respond. The home is in a quiet...
Luxury Suite in Glen Ellyn, IL USA

Geneva Island Park Retreat

10.0 out of 10, Exceptional, (23)
"Perfect home to accommodate our family. It’s a well appointed home, in a splendid location to walk to town. "
Geneva Island Park Retreat

Charming King Bed, Wi-Fi St. Charles

10.0 out of 10, Exceptional, (2)
"While the yard lacked care & maintenance the inside was super clean & provided many upscale features. Soft linens on firm beds, kitchen amenities with brand name, not generic, products. VRBO photos match - it is as shown."
The price is AU$890
includes taxes & fees
10 Dec - 11 Dec
Charming King Bed, Wi-Fi St. Charles

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

10.0 out of 10, Exceptional, (16)
"Exactly what we expected. Excellent place to stay"
Home w/ Office + Yard: 25 Mi to Downtown Chicago!

Cozy 4-bedroom house , 3-full baths in marvelous West Chicago with WiFi, AC,

2.0 star property
Cozy 4-bedroom house , 3-full baths in marvelous West Chicago with WiFi, AC,

Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

2.0 star property
10.0 out of 10, Exceptional, (4)
"This updated home is immaculate and had all the items necessary to move in and enjoy a family vacation for 3 days. The kitchen is well appointed with a gas range and all cookware that is needed. The bathrooms are well stocked with towels. Check in and checkout was easy. We appreciated finding this place to stay close to family who live in the area."
Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville

2.0 star property
10.0 out of 10, Exceptional, (2)
"Wow! I cant stress enough how amazing this place is. Tucked away on a cul de sac street and very quiet. The nice quaint aesthetic is so charming. Once stepping inside my family and I were blown away by how clean, spacious and well decorated it was. It was so cozy and comfortable. The kitchen offered everything you may need. We were able to enjoy the spacious backyard and enclosed patio space. The overall location was great since i have family in plainfield and joliet. We absolutely enjoyed our...
Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville
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 Plainfield

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 10

10.0 out of 10, Exceptional, (24)
"Very clean, activities for all ages"
WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 10

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (71)
"Plenty of space. Great location. We enjoyed our stay very much. My only suggestion would be go in the day before guest check in and make sure everything smells and looks clean. "
Furnished Private home in Aurora sleeps 9 guests

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (15)
"Older property which matched description well. Comfortably fit 5 adults and teens for 4 night stay. Quiet neighborhood even though it is right next to highway. Grocery store within a few mins. We traveled several times to downtown Chicago and Rosemont without issues (other than normal chicago traffic). There are stairs from any entrance, so just be prepared if you have a heavy cooler like we did. :) Could have been a bit cleaner, but that would not stop me from staying again. The host...
The price is AU$709
includes taxes & fees
2 Dec - 3 Dec
LUXE 3 BR, 2 BA + Hot Tub
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.