Best Vacation Homes in Crestwood
Condo
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $80/Night
7 Nights - US $562
Villa
10.0(5 Reviews)
4 Bedrooms
2 Baths
7 Guests
1097.92 ft²
Pet Friendly- Parking
Air Conditioner
Child Friendly
US $232/Night
7 Nights - US $1,624
Hotel
8.8(600 Reviews)
1 Bath
Pool
Breakfast- Parking
Internet
US $146/Night
7 Nights - US $1,024
Apartment
9.6(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $211/Night
7 Nights - US $1,478
Apartment
8.2(5 Reviews)
3 Bedrooms
1 Bath
7 Guests
947.22 ft²
Oceanfront
Spa- Fireplace/Heating
Ocean View
US $213/Night
7 Nights - US $1,493
Apartment
9.0(28 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $178/Night
7 Nights - US $1,249
Apartment
8.8(21 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
US $177/Night
7 Nights - US $1,240
Apartment
8.0(6 Reviews)
2 Bedrooms
1 Bath
31 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $341/Night
7 Nights - US $2,386
Crestwood Luxury Rentals
Apartment
2 Bedrooms
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,467/Night
7 Nights - US $10,270
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $684/Night
7 Nights - US $4,790
House
6 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $598/Night
7 Nights - US $4,186
New
House
4 Bedrooms
2 Baths
8 Guests
129.17 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $474/Night
7 Nights - US $3,320
House
9.6(62 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $401/Night
7 Nights - US $2,807
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
14 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $381/Night
7 Nights - US $2,666
House
9.2(19 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $374/Night
7 Nights - US $2,621
House
8.4(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $353/Night
7 Nights - US $2,471
Crestwood Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
6 Guests
- Pet Friendly
- Child Friendly
Designated Smoking Area
US $202/Night
7 Nights - US $1,412
New
Apartment
1 Bedroom
2 Baths
4 Guests
1097.92 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $216/Night
7 Nights - US $1,511
Hotel
6.2(689 Reviews)
1 Bath
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $81/Night
7 Nights - US $569
House
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Child Friendly
- Designated Smoking Area
US $152/Night
7 Nights - US $1,064
Apartment
3 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $275/Night
7 Nights - US $1,925
House
1 Bedroom
1 Bath
4 Guests
1550 ft²
Hot Tub- Spa
- Fireplace/Heating
- Balcony/Terrace
US $78/Night
7 Nights - US $548
Apartment
10.0(5 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $207/Night
7 Nights - US $1,449
House
9.8(12 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $272/Night
7 Nights - US $1,904
Crestwood Large Vacation Homes
Apartment
4 Bedrooms
3 Baths
10 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
US $330/Night
7 Nights - US $2,313
New
House
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $323/Night
7 Nights - US $2,263
House
10.0(1 Review)
4 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $506/Night
7 Nights - US $3,539
House
9.6(4 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $652/Night
7 Nights - US $4,565
Apartment
8.0(1 Review)
5 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Child Friendly
TV
US $280/Night
7 Nights - US $1,958
House
5.8(6 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $324/Night
7 Nights - US $2,265
House
3 Bedrooms
1 Bath
12 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $295/Night
7 Nights - US $2,064
House
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $301/Night
7 Nights - US $2,108
Why Choose Rent By Owner for your Crestwood 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 Crestwood
When should you plan your Vacation Rentals stay?
Discovering the ideal time to visit here ensures you make the most of your stay, whether you're seeking pleasant weather or off-peak rates in this charming destination.
Peak Season Highlights
Summer (June to August)
During the summer months, the area's warm weather makes it an ideal time for outdoor activities and exploring local attractions in this region.
Average Temperature Daytime: around 80°F - Nighttime: around 65°F
Fall (September to November)
Autumn offers a pleasant climate with vibrant foliage, making it a perfect season to enjoy the natural beauty and seasonal events here.
Average Temperature Daytime: around 70°F - Nighttime: around 50°F
Off-Season Highlights
Winter (December to February)
In winter, cooler temperatures and fewer visitors create a tranquil atmosphere, ideal for those seeking a more relaxed stay in the area.
Average Temperature Daytime: around 35°F - Nighttime: around 20°F
Spring (March to May)
Early spring brings mild weather and blossoming scenery, offering a quieter period before the busy summer season begins.
Average Temperature Daytime: around 55°F - Nighttime: around 40°F
Weekly Weather Forecast for Crestwood
How to Book Your Crestwood 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 Crestwood
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 access to a private outdoor patio or deck, perfect for relaxing or entertaining amidst the fresh air.
- Take advantage of a spacious yard or garden area suitable for outdoor activities or simply enjoying the sunshine.
- Make use of on-site parking facilities designed to accommodate your outdoor needs during your stay.
- Benefit from outdoor lighting that allows you to extend your evenings outside safely and comfortably.
- Relax in a designated seating area outdoors, ideal for reading, dining, or socializing with loved ones.
- Utilize a barbecue grill or outdoor cooking space to enjoy meals prepared in the fresh air during your visit.
- Explore nearby outdoor recreation options, such as parks or walking trails, available within easy reach here.
Top Attractions Around Crestwood
What attractions are nearby?
While staying here, you'll find plenty of opportunities to explore local parks, cultural attractions, and dining options that highlight the best of the area’s community spirit and natural beauty.
Family Activities
- Local Shopping Centers: Explore the area's shopping centers for family-friendly stores and entertainment options that cater to all ages.
- Community Parks and Playgrounds: Spend a day at the nearby parks, enjoying playgrounds, open green spaces, and picnic areas perfect for a relaxing family outing.
- Recreational Sports Facilities: Engage in various sports activities at local recreational facilities designed to keep the whole family active and entertained.
- Family-Friendly Dining Options: Discover the region's eateries that offer menus tailored for children and families, making meals enjoyable for everyone.
Adult Activities
- Golfing at Hickory Hills Country Club: Enjoy a relaxing round of golf at this well-maintained course nestled near the region, perfect for outdoor enthusiasts seeking leisure activities.
- Exploring nearby parks and nature reserves: Take advantage of the area's scenic green spaces and walking trails that offer a peaceful retreat just minutes from your vacation rental.
- Cultural experiences at local community centers: Engage in enriching activities and events hosted within the region that showcase its vibrant local culture and art scene.
- Dining at regional restaurants: Savor the flavors of the area by visiting popular dining establishments known for their welcoming atmosphere and regional cuisine offerings.
Crestwood Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's diverse restaurants to enjoy authentic local cuisine during your stay.
- Plan Visits to Nearby Attractions: While here, include some flexible plans to explore regional points of interest that highlight this destination's unique charm.
- Check Access to Transportation: Ensure your accommodation is conveniently located near public transit or major roads for easy travel around the region.
- Utilize Seasonal Activities: Depending on the time of year, engage in seasonal outdoor activities available nearby to enrich your visit to this area.
Transportation Options
- Metra Commuter Rail: You can conveniently access Chicago and surrounding areas via the Metra commuter rail, making it an ideal option for exploring the broader region from your Crestwood stay.
- Chicago Midway International Airport: This major airport nearby provides easy domestic flights, ensuring smooth arrivals and departures during your visit to this part of Illinois.
- Local Bus Services: Public transportation within the area offers reliable connectivity to key locations, helping you navigate Crestwood and beyond with ease.
- Taxis and Ride-Sharing Services: On-demand options like taxis or ride-sharing apps offer flexible and direct transportation around here, perfect for quick trips or travel within the region.
Local Customs Options
- Local Cuisine Appreciation: You’ll find that savoring traditional dishes at neighborhood eateries is a cherished custom in this area, reflecting its diverse culinary heritage.
- Participating in local festivals offers an authentic glimpse into the region's vibrant culture and communal spirit during your stay.
- Respect for Historical Roots: Visitors are encouraged to honor the area's history by exploring local landmarks and understanding their significance to residents.
- Seasonal Celebrations: Engaging in seasonal events, like holiday parades and celebrations, helps you experience the region’s lively traditions firsthand.
Frequently Asked Questions About Crestwood?
1. What are the top vacation rentals in Crestwood?
There are a lot of options in Crestwood. If you plan on staying in the Crestwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Crestwood:
- Full Bed | Non Smoking
- King Bed | Non smoking
- Executive Family Home in quiet Culdesac
- Charming 3-bedroom apartment in superb Chicago with WiFi
- Thirty Day Minimum Condo in Chicago SW Suburbs of Orland Park Illinois
- The Country Life - house
- Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
- Days Inn by Wyndham Calumet Park
- Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
- *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
2. Which vacation homes in Crestwood are best for families?
If you are looking for a family-friendly vacation home in Crestwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Crestwood:
3. How many Rentbyowner vacation rentals are available in Crestwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 174 in the Crestwood 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 Crestwood.
4. What is the cancellation policy for a vacation rental I book in this area?
Cancellation policies vary by listing, so it’s important to review the specific terms on the property’s page before booking. For detailed information, contact the owner directly or consult the listing's cancellation section.
5. Are there any additional fees or charges I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or city taxes may apply depending on the property. Always check the listing details or contact the host to understand all potential costs involved.
6. How do I ensure my reservation is confirmed and secure in this region?
Your reservation becomes confirmed once you complete the booking process and receive a confirmation email. To ensure security, book through the official platform, and reach out to the host if you have any questions about your reservation.
7. Can I find vacation rentals with flexible check-in and check-out times in this destination?
Many hosts offer flexible check-in and check-out options. To find these amenities, filter your search accordingly or contact the host directly to confirm availability and arrangements.
8. What amenities are typically available in vacation rentals throughout the area?
Vacation rentals here often include essential amenities like Wi-Fi, parking, and kitchen facilities. Specific features vary per property, so review each listing carefully or ask the host about the available amenities before booking.
Crestwood Top Rated Vacation Rentals
US $178/Night
7 Nights - US $1,247
US $147/Night
7 Nights - US $1,031
Hotel
8.1(622 Reviews)
1 Bath
434.14 ft²
Private Pool- Fireplace/Heating
- Pool
- Breakfast
US $190/Night
7 Nights - US $1,330
Hotel
8.1(285 Reviews)
1 Bath
- Private Pool
- Pool
- Parking
- Air Conditioner
US $117/Night
7 Nights - US $817
US $128/Night
7 Nights - US $896
Hotel
7.9(235 Reviews)
1 Bath
376.74 ft²
- Private Pool
- Pool
- Parking
- Air Conditioner
US $167/Night
7 Nights - US $1,170
Hotel
5.4(173 Reviews)
3 Baths
326.5 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $131/Night
7 Nights - US $915
House
5.0(1 Review)
4 Bedrooms
5 Baths
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,800/Night
7 Nights - US $12,600
