Vacation rentals in Plainfield

Guest suite in Saint Charles

A serene riverside scene is captured, featuring calm waters that reflect the colors of a sunset. Lush greenery frames the image, with a large tree on the right and a grassy area leading to the riverbank. Clouds scatter softly across the sky.

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!

4.9 out of 5 average rating, 105 reviews

A relaxing outdoor space is depicted at night, featuring a small artisan tiny house and a fire pit surrounded by several chairs. Warm light glows from within the tiny house, and smoke gently rises into the night sky, set against a backdrop of trees.

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

A welcoming living space is bathed in natural light, featuring large windows adorned with elegant curtains. A plush, tufted sofa with decorative pillows invites relaxation. Neutral walls complement the modern décor, which includes a sleek table and artwork, creating a harmonious atmosphere.

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, 11 reviews

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

Alluring Avondale Abode

MichaelRating, 5 stars1 week ago

Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

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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What guests are saying

A Comfortable Stay While You are Away in Oak Park

4.85 out of 5 average rating, 68 reviews1 week ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Home in Austin

What guests are saying

Harbor Inn - Skippin` Stones'

5 out of 5 average rating, 11 reviews7 months ago

We come from Chicago a couple times a year to hike at Starved Rock, Matthiesen, etc, so we thought we would try staying for a full weekend. This place was the perfect fit. It was pet friendly, so our dog could come along, and it had great amenities at the resort. The staff was very responsive and easy to communicate with.

Home in Ottawa

What guests are saying

Spacious 2 Bed Apartment, Perfect Location

4.89 out of 5 average rating, 73 reviews3 weeks ago

This is a quirky, comfortable place. It’s full of great books, interesting decor and Chicago charm. The apartment is quite large, it’s on the ground floor and there is back door access to the alley from the kitchen. The kitchen was full of cookware and there was a gas stove. I appreciated the coffee pot and large tin of Costco coffee. There was also a great selection of teas as well as many interesting mugs to choose from.

Apartment in Lake View

What guests are saying

Blue Door Cottage, Hot Tub & updated 3 BDR ranch

4.97 out of 5 average rating, 32 reviews4 weeks ago

Yes, the place was a bit on the pricier end but I was booking last minute, as I needed to find a place that would house myself, my siblings and their families as we dealt with the death of our Father and getting things together for it. Eric's house was very peaceful and he was an absolute treasure. He was quick to reply whether cell or on the app. He gave me some recommendations on places to take the kids as well. The kitchen had plenty of silverware, dishes and cooking items. There was even tea, coffee and a large assortment of seasonings - I've never seen more than salt and pepper at an airbnb. lol We were all travelling from out of state so the arrival times differed a bit and he was flexible and allowed us to check-in earlier than listed; which was amazing. I personally enjoyed the hot tub, even with the cool weather. It was one of the main things that helped me decide to book this house vs another; as I have low back issues. I would definitely stay there again if able.

Home in Elgin

What guests are saying

Loyola & Lake -3br/2bth close to the Lake & Loyola

4.95 out of 5 average rating, 80 reviews3 months ago

My friends and I stayed for my birthday weekend and were super happy with everything, the fireplace is especially nice for cold chicago winters! We only had trouble finding street parking Saturday night when we got back from our concert at 3am but that was expected. This will be my go-to place for groups from now on!

Apartment in East Rogers Park

What guests are saying

Crestwood Gem

4.85 out of 5 average rating, 13 reviews1 month ago

Great space! We had family coming in from 3 different states and the house was able to accommodate all of us. The kitchen provided all the cookware we needed and was large enough for us to cook as a family. I will say the only real complaint we had was the smell that happened anytime we ran the water. Betty was very responsive and extremely accommodating. We would stay here again! Thank you Betty for sharing your home

Home in Crestwood

What guests are saying

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT!

4.96 out of 5 average rating, 50 reviews2 weeks ago

Beautiful home. We lived the sound system in the living room and the games (pool table, pinball, and arcade machine) in the basement. Property was conveniently connected to a beautiful walking path which also linked up with an awesome park. Last but not least, Ramon was readily available at a moment’s notice. He was a great host.

Home in Plainfield

What guests are saying

Tiny house in West Village Arts District

4.85 out of 5 average rating, 34 reviews3 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

Guesthouse in Evanston

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Popular amenities for Plainfield vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Plainfield's top sights

Jewel-Osco6 locals recommend

Moe Joe's6 locals recommend

Walgreens6 locals recommend

Sovereign6 locals recommend

Louis Joliet Mall5 locals recommend

Target3 locals recommend

Other great vacation rentals in Plainfield

5 out of 5 average rating, 50 reviews

A spacious living area features comfortable seating arranged around a central coffee table. A wall-mounted TV is visible above a white fireplace. Soft lighting is provided by a contemporary chandelier, and large windows are dressed with light curtains, enhancing the room's bright ambiance.

Home in Schaumburg

Great location-King beds-Kids playroom

AdamRating, 5 stars2 weeks 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

An exterior view of a charming blue building with a staircase leading to the entrance. A spacious outdoor area features a large table surrounded by several chairs, complemented by surrounding greenery and decorative plants. Trash bins are located to one side.

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

A concrete pathway leads to a grassy area, bordered by a white fence, with several planters on both sides. The planters include a tall, woven design and a smaller, elegant style, featuring greenery that adds a touch of nature to the outdoor space.

4.86 out of 5 average rating, 77 reviews

Relaxing Suite with Independent Entrance

ErikRating, 5 stars3 weeks ago

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

5 out of 5 average rating, 5 reviews

A modern living space is presented with a white sofa and two accent chairs, arranged around a minimalist coffee table. A dining area is visible in the background, featuring a gold and glass table set with decorative items. Natural light filters in through large windows.

Home in Chicago

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago

Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

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

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago

Peaceful, felt like home, very spacious and comfortable

5 out of 5 average rating, 22 reviews

A modern kitchen features sleek gray cabinetry and a white countertop. Stainless steel appliances are prominent along the back wall, and a window provides natural light over a farmhouse sink. Decorative tile backsplash adds texture, complemented by ample space for meal preparation.

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.