Holiday houses in Naperville

River Views 2BR Haven | Pool, Gym, Pickleball

A premium, resort-like experience in a professionally managed 2-bedroom / 2-bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids' play room, courtyard with firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum, and downtown Chicago, a short drive or train ride away!

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!

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!

True: *NEW* Spacious 5BR-2BT! Fully Fenced Yard!

Welcome to your home away from home! This beautiful 5BR/2BT home offers plenty of room for families or groups to relax and unwind. Enjoy the open layout, comfortable furnishings, and a fully equipped kitchen perfect for home-cooked meals. Step outside to a beautifully landscaped backyard featuring a playset and plenty of space to enjoy the outdoors. Nestled in a peaceful Naperville neighborhood, you’ll be just a short drive from downtown shopping, dining, and family-friendly attractions.

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.

Captivating Home near Naperville

A captivating, newly renovated 3 bedroom / 2 bathroom with fully furnished basement. Clean finishes and modern amenities create the perfect, relaxed space for you and your group. Minutes from downtown Naperville! Walk to downtown Lisle for restaurants, shopping, outdoor events, walk to Lisle train station, Lisle Community Park with walking paths, outdoor summer concerts, playing fields, walk to Prairie Walk Pond with weekly French Market May thru Oct, walk to Sea Lion Aquatic Park.

“The Warrenville Grove”

This bright 2-bedroom home is designed for comfort, with a modern living space, fully equipped kitchen, washer & dryer and a cozy yard to unwind in. Perfect for small groups or families, you’ll be close to local dining, parks, and just a short drive from Naperville and downtown Chicago. We are less than a mile away from the expressway I-88. Whether you’re here for work or leisure, this spot makes it easy to relax, recharge, and explore.

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

The Tailor's Loft, 1 bdrm apt. in Downtown Geneva

The Tailor's Loft is located right the the heart of historic downtown Geneva and is walkable to dozens of unique restaurants and shops. This apartment has been completely renovated in a fresh modern style. It is a great space for a couples getaway, girls weekend or extended stays. High ceilings and open floorpan with separate king-size bedroom. In unit washer/ dryer. Easy walk to the Geneva train station (0.5 miles).

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.

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.

Elegant 4BR Tudor Retreat — Spacious, Peaceful!

Just Renovated! Welcome to your home away from home in beautiful South Naperville. This elegant 4-bedroom, 3-bath English Tudor sits on a peaceful half-acre wooded lot, blending classic charm with modern comfort. Enjoy spacious living areas, a fully equipped kitchen, and cozy corners perfect for relaxation — all just minutes from Downtown Naperville’s shops, restaurants, and scenic Riverwalk.