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Vacation rentals in Darien

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Top-rated vacation rentals in Darien

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

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Guest suite in Wood Dale

4.9 out of 5 average rating, 459 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Home in Lockport

4.95 out of 5 average rating, 117 reviews

Historic Hideaway ~ Vintage 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! 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. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

Home in Lisle

4.93 out of 5 average rating, 110 reviews

Cozy House, Main Road Access, Close to Colleges

Our house is perfect for a small group of friends or family looking for a clean, accessible place. It contains 2 bedrooms (a queen & twin bunk beds) & 1 full bathroom, as well as a sleeper sofa with a pullout queen bed. Enjoy complimentary Hulu & Disney+ with our smart TVs, grill or warm up by the fire pit, & even get some work or studying done! Located just minutes from 2 major highways, 2 colleges, Four Lakes Ski Resort, & much much more, the journey is just getting started once you arrive!

Rental unit in Aurora

4.99 out of 5 average rating, 105 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 brand 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.

Home in Naperville

4.83 out of 5 average rating, 107 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!

Guest suite in Naperville

4.95 out of 5 average rating, 371 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Guesthouse in Villa Park

4.92 out of 5 average rating, 109 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!

Home in Bolingbrook

4.92 out of 5 average rating, 117 reviews

The Sunshine Spot

Relax with the whole family at this peaceful place to stay. Centrally located off I-355 and I-55 major highways . Within walking distance from Promenade Mall ( over 30 plus stores , bars , restaurants ) . Also only about 30 minutes from Chicago. This 3 bedroom ranch has a two car attached garage with private entry ( very safe ) and a huge backyard with Grill . Very spacious and clean ! Thanks and look forward to seeing you at the Sunshine Spot !

Home in Naperville

4.88 out of 5 average rating, 124 reviews

Home away from home

Perfect location, walk/bike to downtown area/ High Speed Wifi throughout the house / 2 King size beds one Queen bed /Newly remodeled / Huge back yard / Brand new appliances / Space for your car in a garage or plenty of parking on long driveway/ Outside porch with seating / Pet friendly - no deposit or any other charge. This is my first house ever listed I will add to the describtion more, after people will notice more things, too many to list.

Tiny home in Burr Ridge

4.92 out of 5 average rating, 339 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Rental unit in Naperville

4.88 out of 5 average rating, 161 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.

Rental unit in Palos Hills

4.94 out of 5 average rating, 164 reviews

Aunt Linda's Apartment with a View in Palos

Sunny, quiet, modest first floor 2 bedroom apartment in owner occupied 4-Flat apartment building. It is located in the Southwest corner of Chicago’s Cook County. It will easily accommodate 4 adults and 2 children [Note: long term stays are available.] The building's eastern view overlooks the southern suburbs of Chicago Ridge, Oak Lawn and Bridgeview.

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Popular amenities for Darien vacation rentals

Free parking on premises

Air conditioning

Stay near Darien's top sights

Waterfall Glen Forest Preserve11 locals recommend

The Promenade Bolingbrook11 locals recommend

Meijer10 locals recommend

Nashville Street Tacos6 locals recommend

Mago Grill & Cantina5 locals recommend

Hollywood Blvd Cinema5 locals recommend

Other great vacation rentals in Darien

Home in Clarendon Hills

4.89 out of 5 average rating, 28 reviews

3 Bedroom+Office*Huge Sofa*Chic Decor*Garden*5 TVs

Home in Romeoville

4.97 out of 5 average rating, 33 reviews

Beautiful Home

Dome in Naperville

4.9 out of 5 average rating, 71 reviews

Professionally Sanitized - Dome Away From Home

Rental unit in Summit

4.96 out of 5 average rating, 71 reviews

2BR Apartment Near Chicago

Home in Lisle

4.87 out of 5 average rating, 45 reviews

Captivating Home near Naperville

Home in Bolingbrook

4.79 out of 5 average rating, 39 reviews

Peaceful Bolingbrook Getaway

Home in Chicago Ridge

4.93 out of 5 average rating, 100 reviews

Quiet cul-de-sac with huge fenced in backyard

Rental unit in Lisle

5 out of 5 average rating, 7 reviews

Taste of Chicago | Cozy & Central Location!

Quick stats about vacation rentals in Darien

Total rentals
30 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
510 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Do house rentals in Darien have wifi?
Absolutely! We offer over 20 house rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Darien?
Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Darien?
Yes! Work meets play with ease at over 10 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Darien have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Darien have free parking?
Absolutely! We offer over 20 house rentals with free parking in Darien. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Darien?
Experience the best of Darien with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Darien?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Darien have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Darien. Enjoy a tailored experience with all the comforts you desire.

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