Vacation rentals in Naperville

Apartment in Lincoln Park

A large dining table made of wood is surrounded by minimalist lighting fixtures. Natural light enters through multiple windows, highlighting the room's mix of exposed brick and modern furnishings. A cozy seating area is visible, featuring a sectional sofa and a television mounted on the wall.

5 out of 5 average rating, 254 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

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, 137 reviews

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, friendly ducks, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🦆🪻🏡

4.96 out of 5 average rating, 338 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

4.92 out of 5 average rating, 252 reviews

Three kayaks, in shades of blue and green, rest on a grassy area near the Fox River. The gentle water flow can be seen in the background, with trees lining the riverbank, reflecting a peaceful outdoor setting.

Home in South Elgin

Riverfront rental with fun activity

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

4.8 out of 5 average rating, 160 reviews

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Lincoln Park

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Apartment in West Lake View

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 177 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

4.88 out of 5 average rating, 169 reviews

A modern living area features a spacious blue couch and two black reclining chairs facing a wall-mounted television. A light-colored coffee table sits in front, with a decorative plant in one corner. Natural light fills the space, highlighted by hardwood flooring.

Home in Lake View

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

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

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

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

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

4.94 out of 5 average rating, 115 reviews

The entrance is characterized by elegant stone steps leading to two ornate wooden doors. Flanking the entry, flower boxes add a touch of color. The structure features large windows, allowing natural light to brighten the facade, and is complemented by a decorative wrought-iron fence.

Apartment in Lake View

The Wrigley Flats | Chicago Vacation Rental

The Wrigley Flats is a unique Chicago vacation rental located 4 blocks south of Wrigley Field in city’s most sought after north side neighborhood---Wrigleyville! Our 3 bedroom | 1 bathroom flat can be rented for a weekend getaway, a week long vacation or an extended stay. Close proximity to Chicago’s lakefront, vibrant nightlife, the eclectic dining scene & of course Wrigley Field; it’s no wonder visitors flock here to get a taste of something amazing!

Guest suite in Naperville

A scenic view of a tranquil lake is framed by vibrant yellow pansies in planters. Lush green grass extends to a black fence bordering the water, while trees and distant greenery create a peaceful backdrop under a blue sky.

4.95 out of 5 average rating, 414 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.

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!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Naperville vacation rentals

Self check-in

Monthly stays

Pet friendly

Laptop-friendly workspace

Gym

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

House rentals in Naperville

4.94 out of 5 average rating, 125 reviews

Home in Lincoln Park

Spacious Full Home Near the Heart of Wrigleyville

4.92 out of 5 average rating, 39 reviews

A well-lit bedroom features a spacious bed adorned with light gray bedding. A large mirror and a television are positioned against the wall, complemented by a lamp providing additional light. Soft curtains frame a window overlooking the outdoor area.

Home in Aurora

Spacious family friendly home away from home

5 out of 5 average rating, 11 reviews

A bright dining area features a large wooden table surrounded by black chairs. Natural light filters through sheer curtains, enhancing the space. A rectangular mirror hangs on the wall alongside a console table adorned with decorative vases, adding a touch of elegance.

Home in Des Plaines

Des Plaines Home

4.93 out of 5 average rating, 153 reviews

The exterior of the duplex showcases a charming facade with large windows and a distinctive oval entrance. A well-maintained garden, framed by a black iron fence, adds a touch of greenery to the welcoming entrance. Stairs lead up to the front door, enhancing accessibility.

Home in Lake View

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

4.86 out of 5 average rating, 124 reviews

A spacious living area features a dark sectional sofa adorned with yellow accent pillows, complemented by a cozy throw blanket. A circular mirror hangs above a standing lamp, while decorative wall art adds visual interest. A dining table with chairs is situated in the background.

Home in Austin

Urban Chic 3beds w/2bath + free parking & W/D

4.8 out of 5 average rating, 44 reviews

The living room features a neutral color palette with comfortable seating, including a dark couch and armchair. A coffee table sits centrally on a patterned area rug, while large windows allow natural light to fill the space, creating a welcoming atmosphere.

Home in Glendale Heights

Spacious 4 Bed Room suburban home

4.81 out of 5 average rating, 194 reviews

The image presents a two-story home with framed cedar bevel siding. A welcoming front porch features wooden railings and steps leading to the entrance. Surrounding greenery adds a natural touch, while the well-maintained pathway and lawn contribute to the property’s inviting exterior.

Home in Blue Island

Warm and comfortable inviting Suburban home !

4.73 out of 5 average rating, 124 reviews

A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.

Home in Markham

The Country Life! Entire House.

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Private vacation rentals in Naperville

4.95 out of 5 average rating, 161 reviews

A bright living area features a light-colored sectional sofa, a coffee table, and a television stand. Natural light enters through three large windows adorned with wooden blinds. A floor lamp provides soft illumination, complemented by a rug with intricate patterns on the hardwood floor.

Condo in Logan Square

Logan Square living at its best w/ bright 2 bdrm

4.92 out of 5 average rating, 60 reviews

An updated kitchen area features a gas stove and a sleek stainless steel refrigerator. A round dining table is positioned near a large window, surrounded by four chairs. Natural light streams in, enhancing the open layout with modern finishes and a neutral color palette.

Bungalow in Streamwood

Tranquil tiny cottage by golf club-senior friendly

4.9 out of 5 average rating, 200 reviews

A brightly colored bedroom showcases a spacious bed adorned with a vibrant duvet. Natural light filters through large windows, illuminating the minimalist decor featuring a ceiling fan and playful wall art.

Home in Wicker Park

Tropical Penthouse in Wicker Park w/Backyard Patio

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.

4.78 out of 5 average rating, 9 reviews

The Hidden Beach House

4.86 out of 5 average rating, 125 reviews

The open dining area features a wooden table set with a decorative centerpiece. A modern kitchen is visible in the background, showcasing stainless steel appliances and a sleek design. A staircase leads to the second level, and large windows allow natural light to fill the space.

Bungalow in Morgan Park

Relax.Relate.Release in our Bungalow

4.89 out of 5 average rating, 125 reviews

A modern two-story house features a light, neutral exterior with decorative shutters. The inviting front yard is well-maintained, including colorful shrubs and a manicured lawn. A garage door is visible on the right side, and tall trees frame the property against a clear blue sky.

Home in Naperville

California King Bed | Fast Wi-Fi | 75" Smart TV

5 out of 5 average rating, 4 reviews

The exterior of the home is showcased, featuring a wooden facade, a prominent balcony above large windows, and a spacious driveway. Soft landscaping surrounds seating arrangements near the entrance. A garage structure is visible to the right, with trees and open space in the background.

Home in Wood Dale

Home in the Woods!

4.93 out of 5 average rating, 224 reviews

Home in Justice

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

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Pet-friendly vacation rentals in Naperville

4.95 out of 5 average rating, 203 reviews

A modern kitchen features sleek gray cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. Natural light enters through a window above the sink, where a small flower arrangement is placed. The wood-inspired flooring complements the contemporary design.

Apartment in Joliet

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

4.83 out of 5 average rating, 178 reviews

A living room is presented with a large blue sectional sofa and a light-colored throw draped across it. A small transparent coffee table sits in front of a seated dog, adding a cozy touch to the space. Natural light filters through large windows, enhancing the inviting atmosphere.

Apartment in Evanston

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

4.91 out of 5 average rating, 340 reviews

A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.

Condo in Logan Square

Susie's Space. 2BR easy parking & pet friendly

4.84 out of 5 average rating, 134 reviews

A shared yard features a lush green lawn surrounded by trees and a fence. A small patio area includes a table and chairs, with an umbrella providing shade. A barbecue grill is positioned next to the side of the unit, and a garden area is visible in the background.

Apartment in Wilmette

Downtown Wilmette Micro Studio

4.85 out of 5 average rating, 120 reviews

A spacious backyard is surrounded by a wooden fence, featuring a well-maintained lawn. A large tree offers shade, while a set of red outdoor chairs is positioned around a small firepit. A children's playset is visible in a corner, enhancing the family-friendly atmosphere.

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

4.82 out of 5 average rating, 179 reviews

A cozy living area features a comfortable sofa against a sloped wall, complemented by two dark blue armchairs. Skylights above provide ample natural light, illuminating a patterned area rug beneath a wooden coffee table. Framed artwork hangs on the adjacent wall.

Apartment in Austin

Reno btrm; Big family escape, W/parking, love pets

4.84 out of 5 average rating, 114 reviews

A charming residential street is lined with historic brick buildings, showcasing architectural details such as rounded bay windows and decorative cornices. Lush trees provide shade along the sidewalk, with parked cars and softly glowing street lamps contributing to a serene atmosphere in the early evening light.

Townhouse in Lake View

Wrigleyville townhome two blocks from ballpark