Vacation rentals in Westchester

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Top-rated vacation rentals in Westchester

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

Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 421 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 .

Jul 15 – 22

$113 per night
Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 232 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.

Aug 27 – Sep 3

$98 per night
Guest favorite

Apartment in Hillside

4.83 out of 5 average rating, 143 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

Apr 1 – 8

$86 per night

Popular amenities for Westchester vacation rentals

Other great vacation rentals in Westchester

Superhost

Apartment in Berwyn

4.87 out of 5 average rating, 111 reviews

2 bd/1 bth Berwyn Apt 20 mins frm Chgo

Apr 13 – 20

$108 per night
Superhost

Apartment in Oak Park

4.84 out of 5 average rating, 481 reviews

Sunny Jumbo Studio NO cleaning fee!

Dec 31 – Jan 7

$110 per night
Guest favorite

Home in Westchester

4.98 out of 5 average rating, 47 reviews

Jacuzzi, King Beds, Easy Access to DT Chicago!

May 17 – 24

$312 per night
Guest favorite

Apartment in Westchester

5.0 out of 5 average rating, 14 reviews

Short Drive to Hospitals/Airports/Downtown Chicago

Apr 20 – 27

$134 per night
Guest favorite

Guesthouse in Villa Park

4.94 out of 5 average rating, 65 reviews

Eclectic Coach House Apartment

Feb 19 – 26

$129 per night
Superhost

Home in Maywood

4.86 out of 5 average rating, 56 reviews

Maywood Relaxation

Feb 14 – 21

$123 per night
Guest favorite

Guesthouse in Villa Park

4.81 out of 5 average rating, 27 reviews

Tranquil Pondview +New Kitchen

Aug 25 – Sep 1

$101 per night
Guest favorite

Home in Westchester

4.96 out of 5 average rating, 28 reviews

Triple the Charm: 3 Bedroom Home

Nov 24 – Dec 1

$262 per night
Superhost

Home in Westchester

4.9 out of 5 average rating, 10 reviews

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

Aug 5 – 12

$434 per night
Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 85 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Jun 30 – Jul 7

$103 per night
Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 76 reviews

1 bedroom garden apartment in Forest Park

Feb 6 – 13

$95 per night
Guest favorite

Apartment in Forest Park

4.93 out of 5 average rating, 42 reviews

Enjoy the Chicago | Modern 2 Bedroom Apartment

Apr 17 – 24

$100 per night

Quick stats about vacation rentals in Westchester

Total rentals

20 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

150 reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Westchester?

    Yes! Work meets play with ease at over 10 vacation rentals in Westchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 a kitchen, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, 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.

Destinations to explore

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  2. United States
  3. Illinois
  4. Cook County
  5. Westchester