Holiday rentals in Naperville

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Top-rated holiday rentals in Naperville

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Top guest favourite
A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.
Home in Glen Ellyn
4.92 out of 5 average rating, 190 reviews

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Top guest favourite
A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield
4.92 out of 5 average rating, 147 reviews

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Top guest favourite
A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.
Guest suite in Saint Charles
5 out of 5 average rating, 305 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Guest favourite
A modern kitchen features dark cabinetry complemented by granite countertops. Stainless steel appliances, including a refrigerator and stove, are present. Two bar stools with circular bases are positioned near the countertop. Pendant lights hang above the island, adding functional illumination to the space.
Flat in Aurora
4.83 out of 5 average rating, 107 reviews

AT YOUR SERVICE! Downtown Aurora River Facing Gem

Welcome to your cozy retreat in the heart of Downtown Aurora! This charming 1-bedroom apartment is perfect for up to 2 guests and offers a peaceful river view. The unit is complete with a full kitchen & is pet-friendly. Located steps from Hollywood Casino, Paramount Theatre, RiverEdge Park, and the scenic Riverwalk, you'll have easy access to local attractions. Stroll to restaurants, shops, and entertainment, making this the perfect base for exploring all that Downtown Aurora has to offer.

Top guest favourite
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
4.87 out of 5 average rating, 155 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 favourite
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
4.87 out of 5 average rating, 158 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 favourite
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.
Flat in Aurora
4.99 out of 5 average rating, 212 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
The living area features a large sectional sofa with decorative pillows, positioned opposite a television mounted on a dark wood unit. Artwork depicting colorful pixel characters adorns the wall. An archway leads to a game room with a pool table and ambient lighting.
Home in Downers Grove
4.9 out of 5 average rating, 124 reviews

Games, Grounds, Goodness in DG

Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Guest favourite
Home in Aurora
4.85 out of 5 average rating, 115 reviews

Naperville/Aurora | Fenced Yard!

Our 3bd, 1.5ba house is perfect for a group of friends or family looking for a clean place in a safe neighborhood on the Naperville/Aurora border. There is plenty of space for 9 people to sleep comfortably (5 beds & a couple comfy couches), as well as 3 smart TVs, a gas grill & large, private, fully-fenced yard (including outdoor games), a desk space, & much more. Enjoy close access to main roads & many restaurants, stores, parks, & other places of need!

Top guest favourite
The exterior of the Coach House features white siding and a covered entry, framed by greenery. Two doors are visible, leading into the house, while a decorative wall piece is positioned above the entrance. A pathway lined with plants guides the way to the front steps.
Guest house in Batavia
4.92 out of 5 average rating, 311 reviews

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Top guest favourite
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, 487 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.

Guest favourite
A cozy living area is presented, featuring a comfortable sofa with decorative cushions and a matching ottoman. Two lamps provide soft lighting, and a large mirror reflects the space. A textured area rug defines the seating arrangement, with stair access visible in the background.
Flat in Downtown Naperville
4.88 out of 5 average rating, 185 reviews

Comforts of home in downtown Naperville

Cozy 1 bedroom garden level apartment located in downtown Naperville. Short walking distance to great shopping and many fine restaurants. Also short walking distance to train which goes directly to Chicago. Parking is available for 1 car in driveway. Professionally cleaned after every guest visit, as well as free cleaning offered for stays of two weeks or longer.

Popular amenities for Naperville holiday rentals

When is the best time to visit Naperville?

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Avg. price$188 SGD$182 SGD$215 SGD$219 SGD$225 SGD$230 SGD$236 SGD$230 SGD$211 SGD$223 SGD$207 SGD$227 SGD
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Frequently Asked Questions

  • What are the best places to stay in Naperville?

    Downtown Naperville is frequently suggested for easy access to dining, shopping, and the Riverwalk. Residential areas near parks and schools are also popular for a quieter, family-friendly atmosphere.

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

    Families often enjoy the DuPage Children's Museum, splashing at Centennial Beach in warmer months, and exploring local playgrounds or nature centers. Seasonal events and interactive exhibits make downtown especially engaging for children.

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

    Explore the Riverwalk’s scenic paths, visit Naper Settlement for local history, and enjoy shopping or dining in the downtown area. Many visitors also relax at parks or catch performances at local theaters.

  • How is the weather in Naperville?

    Naperville experiences cold, snowy winters around 19–37°F (-7 to 3°C) and warm summers near 65–85°F (18 to 29°C), with moderate rainfall throughout the year. Spring and fall have milder temperatures and changing foliage.

  • When is the best time to visit Naperville?

    Late spring and early fall are often recommended for mild temperatures, blooming gardens, and outdoor events. Summer brings warm days suited for patio dining and riverfront strolls.

  • What are the best places to visit in Naperville?

    Explore the Riverwalk, visit Naper Settlement for historic exhibits, and enjoy interactive experiences at the DuPage Children's Museum. Centennial Beach is a favorite seasonal spot for relaxing beside the water.

  • What are some hiking trails in Naperville?

    Naperville has paved paths along the Riverwalk and nature trails in Springbrook Prairie and other local forest preserves. These spots are often recommended for scenic walks, birdwatching, or gentle hikes.

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

    Families often visit the DuPage Children's Museum, swim at Centennial Beach, and enjoy picnics or wildlife spotting in local parks. Seasonal festivals and weekend events add to the city’s welcoming atmosphere.

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

    Consider exploring nearby forest preserves, touring museums in surrounding communities, or visiting botanical gardens around the region. Urban adventures and nature escapes are popular choices close to Naperville.

  • Are there any pet friendly accommodations available in Naperville?

    Many Naperville vacation rentals welcome pets, especially in residential neighborhoods with nearby parks. Listings may include yards or easy access to walking trails for traveling with your dog or cat.

  • What are some local tips for visiting Naperville?

    Stroll the Riverwalk early for quieter views, check community calendars for outdoor concerts or markets, and try locally owned eateries along downtown streets. Bringing comfortable shoes makes exploring easy.

  • What is Naperville known for?

    Naperville is known for its scenic Riverwalk, vibrant downtown, and commitment to historic preservation at sites like Naper Settlement. The city has a reputation for family-friendly activities and thriving community events.

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

    Many enjoy quiet corners of Knoch Knolls Nature Center, art-filled garden paths around downtown, and small neighborhood bakeries. Local parks and tucked-away coffee shops add character to everyday strolls.

  • What are the best foods to try in Naperville?

    Many visitors enjoy locally made pizza, craft burgers, and seasonal Midwest comfort foods. Downtown restaurants frequently feature international options such as Thai, Indian, and Mediterranean cuisine.

  • What should I bring for a trip to Naperville?

    Pack layers for changing Midwest temperatures, comfortable shoes for walking, and a reusable water bottle for outdoor activities. In summer, sunscreen and lightweight clothing are helpful.

  • What is the nightlife in Naperville like?

    Downtown Naperville has lively bars, restaurants, and music venues, creating a welcoming scene for gathering with friends. Some spots regularly feature live entertainment and casual late-night dining options.

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

    Naperville has events like the Last Fling, which is often anchored around Labor Day weekend. Art fairs, music performances, and seasonal community celebrations are frequently suggested throughout the year.

  • Are there family friendly vacation rentals in Naperville?

    Naperville has a variety of family-friendly stays, including homes and apartments in residential neighborhoods near parks, downtown attractions, and schools. Features like full kitchens, extra bedrooms, and outdoor spaces are frequently available.

Quick stats about holiday rentals in Naperville

  • Total holiday rentals

    Explore 200 holiday rentals in Naperville

  • Nightly prices starting at

    Naperville holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    190 of Naperville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Self check-in and Gym across Naperville rentals

  • 4.7 Average rating

    Naperville stays receive an average rating of 4.7 out of 5 from guests

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