Holiday houses in Glendale Heights

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Top-rated holiday rentals in Glendale Heights

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

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Top Guest favourite
Home in Carol Stream
4.92 out of 5 average rating, 128 reviews

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

Top Guest favourite
A cozy living room is furnished with multiple seating options, including wicker chairs and a plush couch decorated with assorted cushions. A round coffee table sits at the center, accompanied by a basket and a small side table. A softly glowing lamp provides warm light, and an electric fireplace is positioned against the wall.
Guest suite in Wheaton
5.0 out of 5 average rating, 65 reviews

The Garden Flat

Discover comfort and charm in this fully renovated LL garden flat, 2 blocks from Wheaton College. Walk to downtown Wheaton and the train. This delightful bungalow, tucked away in a peaceful neighborhood, offers private driveway parking and a lovely fenced backyard with patio. Adorable back porch is perfect for morning coffee or evening wine. Everything you need is waiting at The Garden Flat in Wheaton. A thoughtfully maintained residential home, it’s personally managed to ensure a peaceful stay.

Guest favourite
Campervan/RV in Lombard
5.0 out of 5 average rating, 13 reviews

Couples camper on a quaint horse ranch

Escape to this cozy modern camper located near a small horse barn. Reconnect with nature at this unforgettable escape. Along with the barn animals (horses, goats, and chickens) there is an abundance of wildlife that visits the ranch. Located next to a river and woods with walking trails where you can see deer, coyote, raccoon, possum, chipmunks, rabbits, eagles, owls, hawks, heron, ducks & more. A perfect blend of nature and modern conveniences and easy to get to location in the Chicago burbs.

Top Guest favourite
A charming house with a unique octagonal turret is surrounded by lush greenery and flowering plants. A white picket fence delineates the front yard, providing a cozy and inviting exterior. The home’s shingled roof and multiple windows enhance its architectural character.
Home in Glen Ellyn
4.96 out of 5 average rating, 26 reviews

The Davis House,

The house is located in Historic Glen Ellyn, just a few blocks away from the quaint downtown with shops and restaurants. Also the train which takes you to Chicago is there also. Our location is so secluded. We are on a cul-de-sac and the house has a large, private front yard, surrounded by a tall hedge. For families with younger children we have Babcock Grove Park which is less than a block away. Lake Ellyn Park is only a 10 minute walk . There is a childrens area and foot path around the lake.

Top Guest favourite
A spacious ranch house is depicted, surrounded by matured trees and a well-maintained lawn. The facade features a combination of brick and siding, with a large garage and a welcoming front porch. Sunlight filters through the leaves, creating a serene atmosphere.
Home in Itasca
4.99 out of 5 average rating, 89 reviews

RANCH, House-tel: updated full kitchen, comfy beds

Ranch House with 3 bedrooms, 3 queen beds and 2 full bathrooms, spacious living room, 2 car garage and a long driveway. Lovely, quiet and safe neighborhood with matured trees making your stay a relaxing one while viewing the backyard. About 20 minutes to O’hare airport, just over 10 minutes to the Woodfield Mall/Schaumburg business district, approximately 30-45 minutes to downtown Chicago-largest Starbucks in the world, Skydeck and The Bean. Few minutes drive to restaurants and groceries.

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
4.85 out of 5 average rating, 184 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 spacious screened-in porch features comfortable seating arrangements, including a sectional sofa and a dining table. A hammock is hung in the corner, providing a relaxed space. Natural light floods in, highlighting views of the surrounding trees and yard, creating a refreshing retreat.
Home in Addison
4.99 out of 5 average rating, 92 reviews

Private & quiet🌲 O'Hare 8mi✈️ D/T Chicago 22mi 🏙

Must agree to all house rules prior to booking (see below under "Other details") Get your zen at this one-of-a-kind private home. Situated on a serene lot adjacent to the forest preserve; steps to the splendid walking path/fishing pond. Feels like a hidden gem in the woods, yet with the convenience of easy access to Rt. 83, Irving Park, I-290, O'Hare (minus the overhead noise), golf, shopping, restaurants, and Metra. Enjoy this peaceful oasis- truly a home away from home!

Guest favourite
The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.
Guesthouse in Villa Park
4.93 out of 5 average rating, 164 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

Guest favourite
Home in Warrenville
4.96 out of 5 average rating, 25 reviews

“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.

Top Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.94 out of 5 average rating, 136 reviews

“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!

Top Guest favourite
A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.
Home in Lombard
4.99 out of 5 average rating, 155 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Superhost
A modern living area is displayed, featuring a blue sectional sofa facing a media console with a television displaying the Netflix logo. Natural light enters through multiple windows, and a small decorative plant is placed on a round coffee table.
Townhouse in Lisle
4.81 out of 5 average rating, 36 reviews

Luxury New Build 3BR Townhome

Experience modern luxury in this brand-new 3-bed, 2.5-bath townhome in Lisle, IL. Enjoy the convenience of an in-unit washer/dryer, spacious 2-car garage. Just minutes from downtown Naperville and the Morton Arboretum, this space offers easy access to shopping, dining & entertainment while also offering stunning landscapes and outdoor activities for nature lovers. Perfect for families or business travelers.

Popular amenities for Glendale Heights holiday rentals