Holiday houses in Naperville

Guest suite in Saint Charles

4.85 out of 5 average rating, 136 reviews

Cozy, Comfy, Close to Downtown

AlexisRating, 5 stars1 month ago

Absolutely loved staying here! I had to be nearby to help my best friend prepare for her wedding. Brooke was a great host and was very responsive. The space is so nice and I would absolutely stay here again. Thank you for the accommodations Brooke!

4.91 out of 5 average rating, 180 reviews

Home in Wrigleyville

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

PegahRating, 5 stars2 weeks ago

Stayed here for a bachelorette and was greeted with a lovely customized message for our bride, music, and a lovely home! Clean, spacious, accommodating for a whole gaggle of gals - and that’s tough to do! We especially appreciated how close the house is to Wrigleyville’s food and bars and some great coffee shops, all while still being far enough away to be quiet at night so we could sleep. Very kind host who let us check out late and made sure we were doing ok the entire time. Overall, so so wonderful! Thank you :)

4.9 out of 5 average rating, 105 reviews

Guesthouse in Oswego

The Loft-Rustic Retreat and Sauna

TaraRating, 5 stars1 month ago

Sara’s place was exactly as described! It was clean and comfortable- very private. The sauna was such a nice luxury! We appreciated all of the little niceties - like coffee , candles, and beach towels for the sauna. It was near everything, but still on a quiet street. Sara was very responsive and friendly. She had great suggestions for breakfast and really made us feel at home. We’d definitely go back!

4.91 out of 5 average rating, 123 reviews

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

YoshiRating, 5 stars1 month ago

This small quaint home packs a HUGE punch when it comes to amenities and that home away from home feel. We couldn't have asked for more in an airbnb during our stay in the Chicago area. From the kuerig, to the decor, to the hot tub to the amazing bathroom and shower, this Airbnb had everything we needed and everything we didn't even know we wanted. I would HIGHLY recommend this airbnb along with the amazing and attentive hosts to anyone traveling through the area.

5 out of 5 average rating, 10 reviews

Home in Avondale

Alluring Avondale Abode

SuhailaRating, 5 stars3 months ago

Beth’s house was one of the best airbnbs I’ve ever stayed in. It was absolutely perfect for a family reunion and there was more than enough space for the 6 of us. The kitchen is a chef’s dream, we loved the board games and outside fire pit, and Beth was an extremely generous host and wonderful communicator. We hope to be back soon!

4.84 out of 5 average rating, 248 reviews

Home in Cedar Lake

Vacation home on south end of Cedar Lake

KatherineRating, 5 stars1 week ago

For our trip this home was perfect. It was near the friends we were visiting, short drive to Lake Michigan, great restaurants in the area, and we loved having a kitchen so we could grab some groceries and save some money on meals. The home is older but so is ours so we felt right at home. Everything was clean as well. We hope to stay here again.

4.95 out of 5 average rating, 104 reviews

Guesthouse in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars3 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

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Popular amenities for Naperville holiday rentals

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Stay near Naperville's top sights

DuPage Children's Museum28 locals recommend

Topgolf17 locals recommend

Studio Movie Grill15 locals recommend

Mesón Sabika15 locals recommend

TGI Fridays15 locals recommend

Fox Valley Mall station13 locals recommend

Other great holiday rentals in Naperville

4.92 out of 5 average rating, 38 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 month ago

Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

5 out of 5 average rating, 50 reviews

Home in Schaumburg

Great location-King beds-Kids playroom

AdamRating, 5 stars1 week ago

Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.

Guest suite in Lincoln Park

4.75 out of 5 average rating, 8 reviews

The Hidden Beach House

GaryRating, 5 stars1 month ago

I enjoyed my stay here. The accommodations were basic, but the place was very clean and quiet, I found the bed very comfortable, and the location was ideal for 1 to 2 people to base out of while enjoying Old Town. The Brown Line train is just a couple of blocks from the house, which made getting to the Loop very convenient. Caid was very easy to reach with any questions. I would stay here again. One recommendation: if you drive here and need a parking pass, make those arrangements well in advance of your arrival, because they can’t be provided at a moment’s notice. I waited until the day before to ask for one and could not get it, so I had to pay $90 to park in a garage.

Guest suite in Plainfield

4.86 out of 5 average rating, 77 reviews

Relaxing Suite with Independent Entrance

ErikRating, 5 stars2 weeks ago

Very nice and clean place to stay at, it was definitely worth the money, I would definitely recommend to anyone👍🏽

4.86 out of 5 average rating, 42 reviews

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars2 weeks ago

Peaceful, felt like home, very spacious and comfortable

5 out of 5 average rating, 22 reviews

Home in Elgin

Little Blue House

BriannaRating, 5 stars3 months ago

Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.