Vacation rentals in Westchester

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Top-rated vacation rentals in Westchester

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Guest favorite

Loft in Forest Park

4.96 out of 5 average rating, 463 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

Dec 9 – 16

R2,445 ZAR per night

Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 427 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 15 – 22

R2,291 ZAR 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

R1,794 ZAR 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

Oct 1 – 8

R2,141 ZAR per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 103 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 26 – Oct 3

R2,733 ZAR per night

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Oct 29 – Nov 5

R1,702 ZAR per night

Guest favorite

Home in Forest Park

4.91 out of 5 average rating, 222 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 24 – Jul 1

R2,995 ZAR per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 238 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

R2,523 ZAR per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 292 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Apr 22 – 29

R1,857 ZAR per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 239 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

Sep 29 – Oct 6

R2,121 ZAR per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 201 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.

Nov 17 – 24

R2,351 ZAR per night

Guest favorite

Apartment in Forest Park

5.0 out of 5 average rating, 217 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.

Sep 6 – 13

R2,278 ZAR 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 Berwyn

4.99 out of 5 average rating, 252 reviews

Berwyn Betty Apartment

Mar 3 – 10

R3,015 ZAR per night

Guest favorite

Home in Westchester

4.97 out of 5 average rating, 31 reviews

Triple the Charm: 3 Bedroom Home

Feb 26 – Mar 5

R3,929 ZAR per night

Guest favorite

Guesthouse in Villa Park

4.92 out of 5 average rating, 72 reviews

Eclectic Coach House Apartment

Oct 16 – 23

R2,900 ZAR per night

Superhost

Home in Westchester

4.9 out of 5 average rating, 10 reviews

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

Oct 19 – 26

R6,051 ZAR per night

Guest favorite

Guesthouse in Villa Park

4.83 out of 5 average rating, 40 reviews

Tranquil Pondview + New Kitchen + King Bed + WFH

Aug 15 – 22

R2,290 ZAR per night

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 88 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Feb 23 – Mar 2

R2,266 ZAR per night

Guest favorite

Apartment in Forest Park

4.87 out of 5 average rating, 15 reviews

City-Accessible Basement Retreat

Jan 1 – 8

R1,691 ZAR per night

Guest favorite

Apartment in Lyons

5.0 out of 5 average rating, 17 reviews

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

Dec 11 – 18

R2,039 ZAR 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 Berwyn

Home in Westchester

Guesthouse in Villa Park

Home in Westchester

Guesthouse in Villa Park

Apartment in Forest Park

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?

Destinations to explore