Vacation rentals in Westchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Westchester

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

0 of 0 items showing

1 of 3 pages

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

G$26,676 GYD 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

G$24,991 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 19 – 26

G$19,541 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

Welcome to your beautifully decorated 3 bed 2 bath home located in Westchester, IL. Features modern décor, and all the amenities you need for a relaxing stay. Enjoy our fully-equipped kitchen, large living room with comfortable seating, and spacious bedrooms with plush bedding. Huge backyard, Wi-Fi, and onsite laundry for your convenience. Our home is conveniently located near top-rated restaurants, shopping, and attractions. Stay with us for a memorable stay. Minutes from Downtown and Airports.

Jan 15 – 22

G$51,183 GYD per night

Guest favorite

Home in Westchester

4.97 out of 5 average rating, 31 reviews

Triple the Charm: 3 Bedroom Home

Escape to our charming 3-bedroom vacation rental home in Westchester, IL. Our comfortable and tastefully decorated house is the perfect place to call home during your next trip to the Windy City. With its prime location just minutes away from all the major attractions, including the Brookfield Zoo, Frank Lloyd Wright Home and Studio, and the Cubs and White Sox stadiums, less than 15 miles from each airport and dowtown chicago and several malls. Location + Decoration= Perfect Vacation. Book Now

Nov 8 – 15

G$48,283 GYD 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!

Oct 11 – 18

G$30,005 GYD 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*

Sep 13 – 20

G$18,567 GYD 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 20 – 27

G$29,309 GYD 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

G$23,145 GYD 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.

Mar 21 – 28

G$25,652 GYD 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.

Oct 14 – 21

G$23,409 GYD per night

Guest favorite

Guest suite in Wheaton

4.85 out of 5 average rating, 99 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

Feb 26 – Mar 5

G$23,387 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

Guesthouse in Villa Park

4.92 out of 5 average rating, 72 reviews

Eclectic Coach House Apartment

Sep 22 – 29

G$31,609 GYD per night

Superhost

Home in Maywood

4.83 out of 5 average rating, 60 reviews

Maywood Relaxation

Jan 30 – Feb 6

G$29,482 GYD 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 13 – 20

G$25,128 GYD 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 8 – 15

G$24,724 GYD per night

Guest favorite

Apartment in Forest Park

4.87 out of 5 average rating, 15 reviews

City-Accessible Basement Retreat

Dec 20 – 27

G$18,453 GYD per night

Guest favorite

Home in Westchester

4.98 out of 5 average rating, 54 reviews

Jacuzzi, King Beds, Easy Access to DT Chicago!

Jul 23 – 30

G$91,169 GYD per night

Guest favorite

Guest suite in Berwyn

4.93 out of 5 average rating, 44 reviews

Best Place to Rest, near Chicago

Jan 19 – 26

G$12,540 GYD per night

Guest favorite

Apartment in Lyons

5.0 out of 5 average rating, 17 reviews

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

Oct 9 – 16

G$23,481 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

Guesthouse in Villa Park

Home in Maywood

Guesthouse in Villa Park

Apartment in Forest Park

Apartment in Forest Park

Home in Westchester

Guest suite in Berwyn

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