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Vacation rentals in Plainfield

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Top-rated vacation rentals in Plainfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
The exterior of a two-story house is presented, featuring a light grey siding and blue shutters. A spacious driveway leads to a two-car garage. Lush greenery surrounds the entrance, with a large tree offering shade and a well-maintained lawn completing the inviting front yard.
Home in Plainfield
4.81 out of 5 average rating, 116 reviews

Tranquil 4BR in Naper/Plainfld

Discover our spacious four-bedroom retreat, featuring a master suite with a luxurious bathroom, two queen bedrooms upstairs, downstairs bedroom with two beds, workspace, and a large TV. The living room offers a smart TV and comfy couch, while the kitchen is fully renovated and equipped. Enjoy outdoor amenities like a fire pit, playground, patio set, and grill. Additionally, an easy access to Route 59, I-55, I-88, dining, shopping, and services. Experience comfort and convenience in this charming

Guest favorite
A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.
Home in Bolingbrook
4.92 out of 5 average rating, 155 reviews

Spacious Bolingbrook Retreat w/ Garage & Yard

Relax with the whole family at this peaceful and spacious 3-bedroom ranch home conveniently located near I-55 & I-355. Walking distance to Promenade Mall, restaurants, bars, shopping, Bass Pro Shop. Enjoy self check-in with smart lock, private attached 2-car garage, large backyard, patio, and grill. Perfect for families, work trips, or weekend getaways. Clean, safe, and only 30 minutes from downtown Chicago and major attractions. Self check-in Free parking Fast Wi-Fi Washer/dryer Backyard/patio

Guest favorite
A spacious bedroom features a king-size bed adorned with a colorful quilt and accent pillows. A wall mural of large ferns creates a vibrant backdrop. A full-size futon is positioned alongside, with a lamp and window allowing natural light to brighten the area.
Home in Joliet
4.92 out of 5 average rating, 239 reviews

The Garden House - Murals and more

Our garden-themed house🌿 located on busy Plainfield Road is minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Joliet Union Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball & St.Joe's Hospital. Minutes from: Chicagoland Speedway, Hollywood Casino, Lewis University & Silver Cross Hospital. 30 min. Southwest of Chicago. 🏡Entire house: 2 Bdr (2 Bd & 1 Futon), Bathroom (new shower), Living Room, Kitchen, Front Deck

Superhost
Apartment in Joliet
4.93 out of 5 average rating, 243 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Our remodeled spacious apartment is located on Plainfield Road, minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Train Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball and St. Joe's Hospital, New Lenox Sports Complex Minutes away from: Chicagoland Speedway, Hollywood Casino, Lewis University and Silver Cross Hospital. 30 minutes from Chicago 3 br (3 Queens beds 1 queen sleeper sofa, queen air mattress), 1 full bath

Guest favorite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.86 out of 5 average rating, 173 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Top guest favorite
A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg
4.94 out of 5 average rating, 871 reviews

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Guest favorite
A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.
Home in Montgomery
4.88 out of 5 average rating, 169 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Top guest favorite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 260 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Superhost
A light-filled living area is presented with a soft blue couch and a glass coffee table atop a textured rug. A comfortable armchair complements the seating arrangement. French doors lead to an outdoor deck, enhancing the connection with nature.
Townhouse in Yorkville
4.79 out of 5 average rating, 169 reviews

Riverfront Townhome in Downtown Yorkville

➢ Everything is sanitized/washed/cleaned after every guest ➢ Right on Fox river ➢ Raging Waves Waterpark - 4.1mi ➢ Yak Shack (Canoe & kayak rental) - 0.8mi ➢ Saw Wee Kee Park - 6mi ➢ Fast, Dedicated Wifi ➢ Free parking in attached garage for 2 compact-size cars + additional free parking onsite. ➢ 3 Smart TVs (Living Room, Bedrooms) ➢ Fully equipped + stocked kitchen / bathroom / laundry ➢ Located Downtown Yorkville ➢ Pack 'n Play ➢ High chair ➢ Kurig coffee maker ➢ King size beds

Top guest favorite
A spacious living area features comfortable seating options, including a recliner and an upholstered chair. Natural light filters through large windows, highlighting the wood cabinetry and kitchen area. A small dining table is positioned near the window, enhancing the inviting atmosphere.
Apartment in Naperville
4.99 out of 5 average rating, 100 reviews

Beautiful, quiet, private, spacious, guest suite.

We offer a private entrance with ramp, private deck, shared screened-in porch, gas fireplace, cable with two T.V.’s, kitchenette, washer/dryer, and beautiful views. Our suite is also a wonderful work from home location. We offer fast reliable WiFi, with office supply and copy centers within five minutes of our suite. The suite is on a single level, with all doors being 36 inches wide for accessibility.

Top guest favorite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 537 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Top guest favorite
A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.
Home in Lockport
4.96 out of 5 average rating, 178 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Popular amenities for Plainfield places to stay

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Plainfield

Top guest favorite
Home in Bolingbrook
5 out of 5 average rating, 15 reviews

A Spacious, Well Stocked, Family-Friendly Retreat

Guest favorite
A spacious bedroom features a large bed dressed in a floral-patterned coverlet. Light beige walls complement the soft carpet. Wooden doors lead to the room's entrance and closet, providing a warm, inviting space.
Private room in Oswego
4.93 out of 5 average rating, 187 reviews

King size bed, Large Room, Quiet, Clean

Top guest favorite
A spacious living area features hardwood floors and high ceilings, providing a welcoming ambiance. Modern furniture includes a light-colored sofa and a round coffee table. An entertainment system is positioned near a large window, while a dining table is visible in the adjacent space.
Home in Aurora
5 out of 5 average rating, 44 reviews

Spacious 4 Beds w/ Yard – Near Naperville, Chicago

Home in Naperville
5 out of 5 average rating, 5 reviews

Naperville Escape, King Bed, Parking, Crib, Patio

The kitchen area is visible, featuring sleek stainless steel appliances and a coffee bar stocked with a variety of Keurig pods. Two bar stools sit at the counter, enhancing the open layout that connects the kitchen to the living area.
Home in Joliet
4.67 out of 5 average rating, 30 reviews

Joliet Retreat: Walk-in Shower + Self Check-in

The family room features a large Sony 85-inch TV mounted on the wall, with comfortable leather seating arranged for optimal viewing. A light wooden floor is complemented by an area rug adorned with subtle patterns. Natural light enters through the window with blinds.
Home in Plainfield
5 out of 5 average rating, 9 reviews

Beautiful home in quiet area with plenty of space

The living room features two dark leather sofas positioned around a circular wooden coffee table. A wall-mounted television displays a streaming service logo, while natural light filters through sheer curtains. A cozy ambiance is created by decorative plants and a soft area rug on the hardwood floor.
Home in Joliet
4.77 out of 5 average rating, 26 reviews

Basement Lounge & Games | LCP Collection

Guest favorite
The exterior of the single-story home is shown, featuring white siding and a welcoming porch with a circular window. A manicured lawn surrounds the house, with a paved walkway leading to the entrance. The property is enclosed by a wooden fence, enhancing privacy.
Home in Plainfield
4.89 out of 5 average rating, 9 reviews

Private Plainfield Retreat w/ Gas Grill + Patio

When is the best time to visit Plainfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,759 GYDG$27,386 GYDG$27,386 GYDG$31,358 GYDG$28,849 GYDG$28,640 GYDG$26,549 GYDG$29,058 GYDG$27,804 GYDG$26,549 GYDG$26,759 GYDG$27,386 GYD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Plainfield?

    Stays near downtown Plainfield allow guests to explore shops, restaurants, and local events on foot. The area around Settlers’ Park is also frequently suggested for easy access to outdoor activities and community spaces.

  • What are the best things to do in Plainfield with kids?

    Families frequently enjoy playgrounds and open spaces at parks like Settlers’ Park, and many visit community splash pads or nature trails in warm weather. Libraries and local museums occasionally feature interactive programs for children.

  • What are some of the best things to do in Plainfield?

    Explore Main Street’s shops and cafés, unwind by the water at Settlers’ Park, and attend seasonal farmers markets or outdoor concerts. Art galleries and public trails provide space to connect with local culture and nature.

  • How is the weather in Plainfield?

    Plainfield has cold, snowy winters with temperatures often between 19–38°F (-7–3°C), and warm summers reaching 68–85°F (20–29°C). Spring and autumn bring mild weather and moderate rainfall, making outdoor activities comfortable for most visitors.

  • When is the best time to visit Plainfield?

    Late spring and early autumn are often recommended in Plainfield for comfortable temperatures and a mix of outdoor festivals. Summer draws visitors with family-friendly events and the longest stretches of warm, sunny days.

  • What are the best places to visit in Plainfield?

    Settlers’ Park is frequently suggested for its scenic views, walking paths, and amphitheater events. Historic downtown Plainfield draws visitors to unique shops, eateries, and community art installations.

  • What are some hiking trails in Plainfield?

    Plainfield has paved and natural trails at parks such as Settlers’ Park, providing gentle routes suitable for families and those seeking a scenic stroll. Nature preserves around town also feature walking paths through prairie and woodland landscapes.

  • What are some family activities we can do in Plainfield?

    Families enjoy playgrounds and picnic areas at local parks, seasonal splash pads, and community programs at the public library. Outdoor movie nights and cultural events invite all ages to participate throughout the year.

  • What are some of the best day trip ideas from Plainfield?

    Explore historic downtown Naperville, stroll through botanical gardens in the region, or experience museums in nearby cities. Nature preserves and public parks around Plainfield are frequently suggested for those interested in hiking or picnics.

  • Are there any pet friendly accommodations available in Plainfield?

    Many accommodations in Plainfield welcome pets, especially private vacation rentals and some locally managed stays. Look for listings with outdoor space or near parks to make travel comfortable for both guests and pets.

  • What are some local tips for visiting Plainfield?

    Locals suggest trying weekend farmers markets for fresh produce and baked goods, and timing visits to downtown during community events for a lively atmosphere. Early mornings are quieter for exploring parks and coffee shops.

  • What is Plainfield known for?

    Plainfield is known for its charming historic downtown, community-focused events, and abundant public parks. The area has roots in early Illinois settlement and continues to grow with independent businesses and family attractions.

  • What are the best hidden gems to explore in Plainfield?

    Plainfield has locally owned shops and cafes tucked along Main Street, plus small art studios and independent boutiques that showcase regional talent. Some visitors enjoy tranquil paths at lesser-known nature preserves around town.

  • What are the best foods to try in Plainfield?

    Plainfield has diverse dining, with pizzerias, barbecue, and American comfort food frequently suggested by locals. International options, including Mexican and Asian cuisines, can be found at locally managed spots around downtown.

  • What should I bring for a trip to Plainfield?

    Pack comfortable walking shoes for exploring downtown and parks, plus layers to adjust to weather that can change with the season. Rain jackets are useful during spring and fall, while sunscreen and hats help during warmer months.

  • What is the nightlife in Plainfield like?

    Plainfield has a relaxed nightlife scene, focusing on casual bars, local pubs, and laid-back restaurants with occasional live music. Many venues feature outdoor patios during warmer months, creating a social atmosphere that invites conversation and community.

  • What are the most popular events or festivals in Plainfield?

    Plainfield hosts a summer festival with live music and food vendors, while holiday parades and seasonal farmers markets are community highlights. Outdoor movie nights and cultural celebrations often take place in local parks during warmer months.

  • Are there family friendly vacation rentals in Plainfield?

    Family-friendly vacation rentals are available throughout Plainfield, including homes near parks and quiet residential streets. Many stays include amenities like extra bedrooms, full kitchens, and outdoor spaces for children to play.

Quick stats about vacation rentals in Plainfield

  • Total vacation rentals

    Explore 30 vacation rentals in Plainfield

  • Nightly prices starting at

    Plainfield vacation rentals start at G$8,362 GYD per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Plainfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Plainfield rentals

  • 4.9 Average rating

    Plainfield stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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