Best Vacation Homes in Westchester
House
10.0(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
Hot Tub
Parking
Internet
Child Friendly
AU $375/Night
7 Nights - AU $2,622
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
1840.63 ft²
Fireplace/Heating
View
Pet Friendly- Parking
AU $501/Night
7 Nights - AU $3,507
Hotel
9.0(1005 Reviews)
1 Bath
Spa
Balcony/Terrace
Breakfast
Kitchen
AU $328/Night
7 Nights - AU $2,299
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
Air Conditioner- Internet
AU $596/Night
7 Nights - AU $4,170
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2002.09 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
AU $342/Night
7 Nights - AU $2,392
Condo
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $288/Night
7 Nights - AU $2,014
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
Ocean View- View
- Kitchen
AU $425/Night
7 Nights - AU $2,972
Condo
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $286/Night
7 Nights - AU $2,003
Westchester Luxury Rentals
House
4 Bedrooms
2 Baths
10 Guests
2250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $1,089/Night
7 Nights - AU $7,626
House
10.0(10 Reviews)
4 Bedrooms
3 Baths
12 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
AU $1,060/Night
7 Nights - AU $7,420
House
8.8(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $833/Night
7 Nights - AU $5,834
House
10.0(5 Reviews)
5 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $825/Night
7 Nights - AU $5,777
House
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
AU $775/Night
7 Nights - AU $5,422
New
Apartment
1 Bedroom
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $697/Night
7 Nights - AU $4,882
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
AU $693/Night
7 Nights - AU $4,854
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $690/Night
7 Nights - AU $4,831
Westchester Pet Friendly Vacation Rentals
Apartment
8.0(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $190/Night
7 Nights - AU $1,329
Apartment
9.3(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
AU $238/Night
7 Nights - AU $1,668
Apartment
8.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $643/Night
7 Nights - AU $4,502
House
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
AU $622/Night
7 Nights - AU $4,354
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $564/Night
7 Nights - AU $3,946
Condo
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $296/Night
7 Nights - AU $2,075
House
10.0(16 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $456/Night
7 Nights - AU $3,191
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $421/Night
7 Nights - AU $2,946
Westchester Large Vacation Homes
House
9.8(20 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
AU $571/Night
7 Nights - AU $3,998
House
4 Bedrooms
2 Baths
10 Guests
2249.66 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
AU $659/Night
7 Nights - AU $4,615
House
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $767/Night
7 Nights - AU $5,372
House
8.0(6 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $640/Night
7 Nights - AU $4,480
House
1 Bedroom
3 Baths
10 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
AU $311/Night
7 Nights - AU $2,177
House
9.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $529/Night
7 Nights - AU $3,706
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $1,122/Night
7 Nights - AU $7,853
House
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $521/Night
7 Nights - AU $3,648
Why Choose Rent By Owner for your Westchester Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Westchester
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience and help you make the most of your stay in this charming region; consider the seasonal weather patterns and local events to find the ideal period for your getaway.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warmer weather and longer daylight hours, making this the ideal time for outdoor activities in the region.
Average Temperature Daytime: around 80°F to 85°F - Nighttime: around 65°F to 70°F
Fall (September to November)
Early fall offers mild weather and vibrant foliage, providing a picturesque setting for your stay during this popular season.
Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F
Off-Season Highlights
Winter (December to February)
This quieter period is perfect if you prefer fewer crowds and lower prices while enjoying the cozy atmosphere of the region.
Average Temperature Daytime: around 35°F to 45°F - Nighttime: around 20°F to 30°F
Spring (March to May)
Late winter and early spring bring moderate temperatures and blooming landscapes, offering a peaceful retreat before the summer rush begins.
Average Temperature Daytime: around 50°F to 60°F - Nighttime: around 35°F to 45°F
Weekly Weather Forecast for Westchester
How to Book Your Westchester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Westchester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for meals al fresco amid the region’s charming surroundings.
- Relish the presence of well-maintained gardens or landscaped yards that add to the outdoor appeal.
- Take advantage of private patios or decks, ideal for relaxing or entertaining outdoors.
- Make the most of outdoor seating arrangements designed for socializing or unwinding while soaking up the local atmosphere.
- Look for properties with access to nearby parks or green spaces for outdoor recreation and leisure activities.
- Some rentals feature outdoor fireplaces or fire pits, great for cozy evenings in this area’s comfortable climate.
- Many vacation rentals offer spacious lawns or play areas suitable for family-friendly outdoor fun in this destination.
Top Attractions Around Westchester
What attractions are nearby?
Within this vibrant region, you can explore a variety of outdoor recreational activities and cultural experiences that make your stay here truly enjoyable.
Family Activities
- Westchester Community Center: Engage in family-friendly activities and programs designed to entertain visitors of all ages within this welcoming community hub.
- Brookfield Zoo: Discover a world of wildlife and conservation efforts at this nearby zoo, perfect for an educational and fun day out with your loved ones.
- Salt Creek Trail: Enjoy scenic walks or bike rides along this popular trail that showcases the natural beauty and outdoor recreation opportunities here.
- Park District Recreation Areas: Spend quality time exploring local parks with playgrounds, sports fields, and picnic spots ideal for family outings in the area.
Adult Activities
- Golfing at Edgewood Golf Course: Enjoy a round of golf at this scenic course, perfect for relaxing and unwinding amidst the area's lush landscapes.
- Visit the Westchester Public Library: Explore a variety of engaging programs and resources that make for an enriching visit in this community-focused region.
- Shopping and dining along Westchester Boulevard: Discover local boutiques and eateries that offer a taste of the area's vibrant neighborhood vibe.
- Recreational activities at Twin Lakes Park: Participate in outdoor pursuits such as walking, picnicking, or simply enjoying the natural surroundings here in the region.
Other Places to Stay in Westchester, IL
Fresh Meadow Golf Club
Westchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Discover the area's renowned eateries and make dining reservations ahead to enjoy authentic Westchester flavors during your stay.
- Plan Your Transportation: Take advantage of nearby public transit or rental services to easily access top attractions and navigate this destination without hassle.
- Engage with Community Events: Check local event calendars to experience authentic regional culture, which can enrich your visit here in the region.
- Book in Advance: Secure your preferred vacation rentals early to ensure a comfortable and convenient stay in this area’s sought-after accommodations.
Transportation Options
- Metra Rail Service: You can access commuter trains that connect to downtown Chicago and other neighboring areas, making it easy to explore the city from your vacation rental in this region.
- Bus Transit Options: Public buses provide convenient transportation within the area and to surrounding suburbs, ensuring flexibility for your travel needs during your stay.
- Taxi and Rideshare Services: Reliable taxi services and rideshare options like Uber and Lyft are readily available here, offering quick and convenient transportation at your fingertips.
- Personal Vehicle Rental: Renting a car provides you with the freedom to explore this destination and its surroundings at your own pace, especially for visits outside the immediate area.
Local Customs Options
- Local Dining Etiquette: In this area, sharing meals and engaging in friendly conversation are valued customs that help you connect with the community during your stay.
- Community Celebrations: Participating in neighborhood festivals and parades offers a genuine way to experience the region's welcoming spirit and local traditions.
- Respect for Residential Privacy: Maintaining quiet hours and respecting private properties are important customs that contribute to the area's peaceful atmosphere.
- Environmental Awareness: Recycling and conservation efforts are embraced here, encouraging visitors to be mindful of their environmental impact during their visit.
Frequently Asked Questions About Westchester?
1. What are the top vacation rentals in Westchester?
There are a lot of options in Westchester. If you plan on staying in the Westchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Westchester:
- Modern 2Bdrm Westchester Home with brand-new out door HOT TUB
- Enamored in Elmhurst
- Your Chicago Hub~ 4 minute Walk to Train~ Pets OK~ Game Room
- Zen in La Grange Park
- Bliss in Brookfield - 5BR, 3BR
- Modern Airport Oasis -Minutes from O'Hare Airport and Downtown Chicago
- Sleeps 10 + Coffee bar + Game Room + Train to CHGO
- Luxury Duplex Living in Westchester
- 13 Mi to Dtwn Chicago Maywood Home with Fireplace
- Elmhurst Gem – Ideal Mid-Term Rental, Top Location
2. How many vacation rentals have private pools in Westchester?
There are 2 vacation rentals with private pools near Westchester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Westchester are best for families?
If you are looking for a family-friendly vacation home in Westchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Westchester:
4. How many Rentbyowner vacation rentals are available in Westchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 112 in the Westchester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Westchester.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual property listing. You should review the specific terms and conditions outlined on each listing or contact the property owner directly to understand their cancellation and refund procedures.
6. How do I ensure the vacation rental I book is suitable for my needs?
To confirm that your chosen property meets your requirements, carefully read the property description, amenities, and reviews. If you have any questions, reaching out to the host will help clarify details before confirming your reservation.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning charges, service fees, or security deposits are often listed in the property details. Always review the total price breakdown before completing your booking and contact the host if you need clarification.
8. Is it possible to extend my stay at a vacation rental in the region?
Extensions depend on the availability of the property at the time of your stay. You should contact the host directly through the booking platform to inquire about extending your reservation and to discuss any potential adjustments or additional costs.
9. What amenities are typically included in vacation rentals in this destination?
Most properties feature essential amenities such as Wi-Fi, parking, and kitchen facilities. Specific features can vary, so it's best to review each listing carefully and communicate with the owner if you require particular amenities during your stay.
Westchester Top Rated Vacation Rentals
AU $246/Night
7 Nights - AU $1,720
Hotel
9.0(1002 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
- Breakfast
AU $266/Night
7 Nights - AU $1,859
Hotel
8.8(383 Reviews)
11 Baths
400.22 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $230/Night
7 Nights - AU $1,611
Hotel
8.4(498 Reviews)
9 Baths
418.6 ft²
- Private Pool
Oceanfront- Hot Tub
- Spa
AU $324/Night
7 Nights - AU $2,268
Hotel
8.2(1004 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
AU $181/Night
7 Nights - AU $1,269
Hotel
7.8(1011 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
AU $166/Night
7 Nights - AU $1,161
Hotel
7.5(424 Reviews)
11 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
AU $183/Night
7 Nights - AU $1,277
Hotel
7.5(98 Reviews)
1 Bath
290.63 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $157/Night
7 Nights - AU $1,098
