Westchester holiday rentals

We found 765 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Westchester that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include Wi-Fi and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Westchester

Showing deals for:20 Nov - 27 Nov

Room
Dining
Outdoor dining
Private kitchen
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,412
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Living area
Interior
Room
Exterior
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

8% off
AU$9,294
for 7 nights, 1 home
AU$1,328 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Room
Interior
Private kitchen
Living area
Very good
(11 reviews)

Charming Home in Portage Park

Chicago

14% off
AU$1,947
for 7 nights, 1 home
AU$278 per night
includes taxes & fees
Charming Home in Portage Park
Exterior
Dining
Interior
Private kitchen
Exceptional
(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

8% off
AU$5,859
for 7 nights, 1 home
AU$837 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining
Interior
Private kitchen
Living area
Exceptional
(39 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,619
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Front Yard View
Living Room
Bedroom 1 (King Size) + 55Inch TV
Patio Deck 2
Exceptional
(22 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$9,788
for 7 nights, 1 home
AU$1,398 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Private kitchen
Interior
Interior
Room
Exceptional
(15 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,697
for 7 nights, 1 apartment
AU$385 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Living area
Interior
Room
Exceptional
(19 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$2,365
for 7 nights, 1 apartment
AU$338 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Room
Interior
Dining
Living area
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,338
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Interior detail
Living area
Dining
Private kitchen
Exceptional
(11 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$3,972
for 7 nights, 1 apartment
AU$567 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Room
Dining
Living area
Private kitchen
Wonderful
(18 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$2,444
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Enjoy a meal in the dining room
Patio
Relax in the living room
Queen Bedroom
Exceptional
(9 reviews)

Modern 2BR with Free Parking in Avondale

Chicago

7% off
AU$2,418
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
Modern 2BR with Free Parking in Avondale
Living area
Interior
Room
Private kitchen
Wonderful
(86 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,892
for 7 nights, 1 apartment
AU$270 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Room
Living area
Dining
Interior
Very good
(5 reviews)

Chicago style apt/Near Hosp/ORD/MDW/DT

Berwyn

8% off
AU$2,461
for 7 nights, 1 apartment
AU$352 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Bathroom
Room
Private kitchen
Dining
Exceptional
(13 reviews)

Chic & Cozy near ORD>MDW>DT>HOSP

Berwyn

8% off
AU$3,048
for 7 nights, 1 apartment
AU$435 per night
includes taxes & fees
Chic & Cozy near ORD>MDW>DT>HOSP
Interior
Breakfast bar seating also available
Fully fenced yard - perfect for fur babies
Master bedroom w/king size memory foam bed
Exceptional
(23 reviews)

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

13% off
AU$4,808
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Room
Dining
Living area
Dining
Exceptional
(31 reviews)

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,212
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Living area
Living area
Interior
Dining
Exceptional
(9 reviews)

Large Renovated Delightful 2nd Floor Suite in Forest Park

Forest Park

9% off
AU$1,661
for 7 nights, 1 apartment
AU$237 per night
includes taxes & fees
Large Renovated Delightful 2nd Floor Suite in Forest Park

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the charming city of Westchester

Learn about the unique charm of Westchester with a stay in a holiday home rental. Travellers especially like the basketball games, shopping and restaurants in this romantic and welcoming city. Wrigley Field and McCormick Place are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Westchester

Do you want to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Westchester has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Galloping Ghost (2.6 mi / 4.2 km)
  • The Dome at the Parkway Bank Sports Complex (9.1 mi / 14.6 km)
  • Rainbow Falls Waterpark (12.4 mi / 20 km)
  • Pirates Cove Childrens Theme Park (12.5 mi / 20.2 km)
  • Cog Hill Golf & Country Club (12.8 mi / 20.6 km)
  • Lincoln Park Zoo (13.6 mi / 21.9 km)

Exploring the natural features in Westchester

Whether you're an outdoor enthusiast or just want to take in the scenery, Westchester is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (13.5 mi / 21.7 km)
  • Grant Park (13.5 mi / 21.7 km)
  • Triton College Botanical Garden (5 mi / 8.1 km)
  • Garfield Park (8.7 mi / 14 km)
  • Garfield Park Conservatory (8.8 mi / 14.1 km)
  • Morton Arboretum (9 mi / 14.5 km)

Travelling to and around Westchester

The nearest airport is in Chicago Midway Airport (MDW), located 8.4 mi (13.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago O'Hare International Airport (ORD), which is 8.9 mi (14.3 km) away.

Frequently asked questions

What is the best area to stay in Westchester when booking a holiday rental?
When considering a holiday rental in Westchester, Illinois, one of the most appealing areas to stay is near the quaint downtown district. This area offers a charming atmosphere with a variety of local shops, cafes, and restaurants that showcase the community's character. It's an excellent spot for those who enjoy a vibrant, walkable environment.Another fantastic option is the neighbourhood close to the Proksa Park. This lovely green space is superb for families and outdoor enthusiasts, featuring walking trails, picnic areas, and playgrounds. The park provides a serene escape while remaining conveniently situated near the heart of Westchester.In terms of properties, Westchester offers a range of options for holiday rentals, from cosy family homes to comfortable apartments, suiting various needs and preferences.
What is the most popular type of holiday rental accomodation in Westchester?
In Westchester, holiday houses are the most popular type of holiday rental, with about 18 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many of these properties also offer outdoor spaces such as gardens or patios, great for relaxing after exploring the local amenities.
Are there pet-friendly house rentals in Westchester?
In Westchester, there are several pet-friendly house rentals available for those looking to enjoy a comfortable stay with their furry companions. Many of these properties come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can roam freely.The neighbourhood itself offers a suburban charm, with nearby parks that are ideal for walks and playtime with pets. Local parks often feature walking trails and open spaces, providing ample opportunities for outdoor activities. Additionally, the area is conveniently located near shops and restaurants that may welcome pets, ideal for those travelling with their animals.
Are there any remote work holiday rentals in Westchester?
In Westchester, Illinois, there are numerous remote work-friendly holiday rentals available, with around 20 properties to choose from. These accommodations cater specifically to those needing to balance work and leisure, offering amenities such as reliable Wi-Fi, dedicated workspaces, and access to third-party internet services. Many properties feature comfortable desks and office areas, allowing for a productive work environment.The area is conveniently located near various parks and recreational facilities, providing opportunities for outdoor breaks and relaxation after a day of work. Local dining options and shops are also within easy reach, adding to the convenience of your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Westchester?
In Westchester, popular rental amenities include provisions for pets, making it a great choice for travellers who wish to bring their furry companions along. Additionally, many holiday rentals feature kitchens that allow guests to prepare their own meals, along with coffee and tea makers for that morning brew. Onsite parking is also a common convenience, ensuring ease of access for those with vehicles.
When is the best time to visit Westchester for a holiday rental?
The peak season for holiday rentals in Westchester falls between May and July, making this the most vibrant time to visit. During these months, the area buzzes with activity as families and tourists flock to enjoy the pleasant weather and local attractions. July, in particular, stands out as the most popular month, where you can take advantage of warm temperatures, typically ranging from 20 to 30 degrees Celsius, superb for outdoor exploration.As you stroll through the charming parks or visit nearby attractions, you'll find that summer in Westchester is ideal for a range of outdoor activities. From leisurely walks to exciting local festivals, there's something for everyone. This period is especially appealing for those seeking a lively option filled with community events.For those looking to save a bit while still enjoying a lovely getaway, consider planning your trip in February. While it's a quieter time, it offers a unique perspective of Westchester, with a chance to enjoy the local community in a more relaxed setting. You might find some delightful deals on holiday rentals, allowing you to explore the area at your own pace, whether it's visiting local museums or enjoying the tranquillity of the parks.Ultimately, the best time to visit Westchester depends on your preference for lively summer experiences or a more serene winter retreat.
What are the top attractions in Westchester?
In Westchester, Illinois, visitors can explore several attractions that highlight the area's charm and activities. The Brookfield Zoo, located just a short drive away, is a fantastic destination for families, featuring diverse animal exhibits and engaging educational programs. The nearby Salt Creek Trail provides beautiful walking and biking paths, great for outdoor enthusiasts looking to enjoy nature.For those interested in history, the Westchester Historical Society offers insights into the local heritage, while the local parks, such as the Westchester Commons Park, provide recreational facilities and picnic areas for relaxation. Additionally, the area has a variety of dining options, from casual eateries to more upscale restaurants, allowing visitors to experience local flavours.
Are all fees included in the Westchester holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Westchester holiday homes with parking?
Stayz offers a wide selection of holiday homes in Westchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Westchester holiday homes?
You can find great discounts on holiday homes in Westchester on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Westchester holiday home booking on Stayz?
To find Westchester holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Westchester?
A long-stay holiday home in Westchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Westchester holiday home?
Book your Westchester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Westchester?
Prices for holiday homes in Westchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Westchester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.