Vacation rentals in Westchester

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Top-rated vacation rentals in Westchester

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Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 425 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 .

Oct 19 – 26

G$25,039 GYD per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 5 – 12

G$18,874 GYD per night

Guest favorite

Apartment in Oak Park

4.85 out of 5 average rating, 527 reviews

Long stays welcome@warm&cute vintage 2BR

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Sep 27 – Oct 4

G$21,883 GYD per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 102 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Sep 11 – 18

G$30,776 GYD per night

Guest favorite

Apartment in Hillside

4.84 out of 5 average rating, 146 reviews

Easy, Cool, safe place to stay.

17 mins Ohare airport 25 mins to downtown Chicago Being closer isn't always better I want you to enjoy your stay, and I don't have rules other than basic ones like noise and guest limit. Have Fun Very safe and quiet 420 might be ok, please message me* 3 Queen-size beds. One is self-iflating inside the middle closet. Well stocked kitchen 2 Private parking lot spaces. Kreuger coffee Smart TV Netflix There is no smoking in the unit or inside building* Coin laundry is available

May 1 – 8

G$24,095 GYD per night

Guest favorite

Home in Forest Park

4.9 out of 5 average rating, 221 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Jun 25 – Jul 2

G$32,273 GYD per night

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 185 reviews

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

Oct 27 – Nov 3

G$25,961 GYD per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 234 reviews

Mid-Century Charm. Near Chicago. Low Cleaning Fee!

Step back in time a bit with our charming 2nd floor walk-up in a quiet, safe suburb. Newly remodeled but with a vintage, welcoming vibe. We're a 20-minute drive to downtown Chicago (depending on traffic). Our home is a 2-unit building. We live in the downstairs unit but the upstairs is all yours and entirely separate. 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

Oct 5 – 12

G$27,670 GYD per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 238 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

Nov 2 – 9

G$23,417 GYD per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 200 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Jan 19 – 26

G$25,586 GYD per night

Guest favorite

Apartment in Forest Park

5.0 out of 5 average rating, 216 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

Aug 7 – 14

G$25,481 GYD per night

Guest favorite

Apartment in Forest Park

4.84 out of 5 average rating, 109 reviews

Home away from home downstairs

Enjoy a stylish experience at this centrally-located, easy access , ground floor apartment. You will have a fully equipped kitchen, laundry facility outside your back door and super fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation.

Nov 7 – 14

G$25,071 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Westchester

Guest favorite

Apartment in Westchester

5.0 out of 5 average rating, 14 reviews

Short Drive to Hospitals/Airports/Downtown Chicago

Jun 6 – 13

G$35,434 GYD per night

Guest favorite

Home in Westchester

4.97 out of 5 average rating, 30 reviews

Triple the Charm: 3 Bedroom Home

Dec 1 – 8

G$48,377 GYD per night

Superhost

Home in Westchester

4.9 out of 5 average rating, 10 reviews

Luxurious Retreat King bed, WI-FI 3bed 2 bath

Dec 10 – 17

G$60,754 GYD per night

Guest favorite

Guesthouse in Villa Park

4.93 out of 5 average rating, 71 reviews

Eclectic Coach House Apartment

Feb 10 – 17

G$30,342 GYD per night

Guest favorite

Guesthouse in Villa Park

4.84 out of 5 average rating, 37 reviews

Tranquil Pondview + New Kitchen + King Bed + WFH

Aug 31 – Sep 7

G$22,790 GYD per night

Guest favorite

Home in Westchester

4.98 out of 5 average rating, 53 reviews

Jacuzzi, King Beds, Easy Access to DT Chicago!

Jul 23 – 30

G$91,960 GYD per night

Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 78 reviews

1 bedroom garden apartment in Forest Park

Mar 10 – 17

G$22,899 GYD per night

Guest favorite

Apartment in Lyons

5.0 out of 5 average rating, 16 reviews

Beautiful & Private, 1bdrm, 1bath w/washer & dryer

Jul 13 – 20

G$22,454 GYD per night

Show all

Quick stats about vacation rentals in Westchester

Total rentals
10 properties
Local attractions
Mariano's, Le Petite Cafe, and Target
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
160 reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Westchester?
Westchester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Westchester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Westchester have wifi?
Absolutely! We offer over 10 house rentals with wifi in Westchester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westchester have free parking?
Absolutely! We offer over 10 house rentals with free parking in Westchester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westchester have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Westchester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westchester have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Westchester. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Westchester

Top-rated vacation rentals in Westchester

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Westchester vacation rentals

Other great vacation rentals in Westchester

Apartment in Westchester

Home in Westchester

Home in Westchester

Guesthouse in Villa Park

Guesthouse in Villa Park

Home in Westchester

Apartment in Forest Park

Apartment in Lyons

Quick stats about vacation rentals in Westchester

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Westchester?

What are the most popular amenities for House Rentals in Westchester?

Do house rentals in Westchester have wifi?

Do house rentals in Westchester have free parking?

Do house rentals in Westchester have air conditioning?

Do house rentals in Westchester have a kitchen?

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