Crestwood Vacation Rentals & Ski-in/Ski-out Homes
New
House
- Chicago
- ·
- Palos Heights
- 0.60 mi to center
5 Bedrooms
4 Baths
10 Guests
Hot Tub
Fireplace/Heating
Pet Friendly
Air Conditioner
US $324/Night
7 Nights - US $2,268
Villa
- Chicago
- ·
- Hazel Crest
- 1.11 mi to center
10.0Exceptional
(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
- Chicago
- ·
- Oak Forest
- 2.08 mi to center
9.0Exceptional
(560 Reviews)
1 Bath
Pool
Breakfast- Parking
Internet
US $133/Night
7 Nights - US $934
Condo
- Chicago
- ·
- Orland Park
- 1.10 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Balcony/Terrace
Kitchen- Parking
US $80/Night
7 Nights - US $562
Apartment
- Chicago
- ·
- Calumet Park
- 0.48 mi to center
8.2Excellent
(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
- Chicago
- ·
- Palos Hills
- 1.37 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $133/Night
7 Nights - US $933
Apartment
- Chicago
- ·
- East Beverly
- 0.47 mi to center
9.6Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,265
Apartment
- Chicago
- ·
- Morgan Park
- 0.23 mi to center
9.2Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
US $161/Night
7 Nights - US $1,129
Apartment
- Chicago
- ·
- Morgan Park
- 0.18 mi to center
9.0Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,082
Luxury Places to Stay in Crestwood
Over 164+ Luxury Places to Stay in or Near Crestwood
Apartment
2 Bedrooms
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,467/Night
7 Nights - US $10,270
House
- Chicago
- ·
- Blue Island
- 1.06 mi to center
6 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $569/Night
7 Nights - US $3,984
House
- Chicago
- ·
- West Pullman
- 0.04 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $495/Night
7 Nights - US $3,466
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
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
14 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $384/Night
7 Nights - US $2,689
House
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $366/Night
7 Nights - US $2,561
House
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $363/Night
7 Nights - US $2,539
House
- Chicago
- ·
- Tinley Park
- 0.54 mi to center
3 Bedrooms
1 Bath
7 Guests
120 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $359/Night
7 Nights - US $2,513
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $347/Night
7 Nights - US $2,426
Top-Rated Vacation Rentals with a Pool in Crestwood
Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Crestwood
Hotel
8.4Excellent
(1347 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $178/Night
7 Nights - US $1,247
Hotel
8.4Excellent
(1070 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $143/Night
7 Nights - US $999
Hotel
8.1Excellent
(585 Reviews)
1 Bath
434.14 ft²
Private Pool- Fireplace/Heating
- Pool
- Breakfast
US $174/Night
7 Nights - US $1,217
Hotel
- Chicago
- ·
- Oak Forest
- 2.10 mi to center
8.1Excellent
(278 Reviews)
1 Bath
- Private Pool
- Pool
- Parking
- Air Conditioner
US $117/Night
7 Nights - US $817
Hotel
8.0Excellent
(240 Reviews)
1 Bath
376.74 ft²
- Private Pool
- Pool
- Parking
- Air Conditioner
US $167/Night
7 Nights - US $1,170
Hotel
- Chicago
- ·
- Oak Forest
- 2.07 mi to center
8.0Excellent
(75 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $107/Night
7 Nights - US $751
Hotel
7.2Very Good
(235 Reviews)
10 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $210/Night
7 Nights - US $1,468
Hotel
- Chicago
- ·
- Oak Forest
- 2.10 mi to center
5.4Average
(173 Reviews)
3 Baths
326.5 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $120/Night
7 Nights - US $840
House
- Chicago
- ·
- Palos Heights
- 0.69 mi to center
5.0Average
(1 Review)
4 Bedrooms
5 Baths
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,800/Night
7 Nights - US $12,600
Pet-Friendly Vacation Rentals in Crestwood
Over 50+ Pet-Friendly Vacation Rentals in or Near Crestwood
Apartment
- Chicago
- ·
- Blue Island
- 0.84 mi to center
8.0Excellent
(5 Reviews)
2 Bedrooms
1 Bath
31 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $335/Night
7 Nights - US $2,348
Apartment
3 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $275/Night
7 Nights - US $1,925
Hotel
6.2Good
(677 Reviews)
1 Bath
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $81/Night
7 Nights - US $569
House
- Chicago
- ·
- Morgan Park
- 0.82 mi to center
2 Bedrooms
1 Bath
6 Guests
- Pet Friendly
- Child Friendly
Designated Smoking Area
US $202/Night
7 Nights - US $1,412
House
- Chicago
- ·
- Hazel Crest
- 1.11 mi to center
4 Bedrooms
1 Bath
7 Guests
1097.92 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $200/Night
7 Nights - US $1,400
House
- Chicago
- ·
- Morgan Park
- 0.68 mi to center
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Child Friendly
- Designated Smoking Area
US $152/Night
7 Nights - US $1,064
House
- Chicago
- ·
- Oak Forest
- 1.23 mi to center
1 Bedroom
1 Bath
4 Guests
1550 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $78/Night
7 Nights - US $548
Apartment
- Chicago
- ·
- East Beverly
- 0.52 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $215/Night
7 Nights - US $1,503
House
9.8Exceptional
(12 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $272/Night
7 Nights - US $1,904
Large Vacation Homes & Villas in Crestwood
Over 16+ Large Vacation Homes & Villas in or Near Crestwood
House
9.6Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $333/Night
7 Nights - US $2,333
House
- Chicago
- ·
- Country Club Hills
- 0.94 mi to center
8.4Excellent
(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $291/Night
7 Nights - US $2,040
Apartment
- Chicago
- ·
- West Pullman
- 0.47 mi to center
4 Bedrooms
3 Baths
10 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
US $330/Night
7 Nights - US $2,313
House
- Chicago
- ·
- Morgan Park
- 0.66 mi to center
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $301/Night
7 Nights - US $2,108
House
- Chicago
- ·
- East Beverly
- 0.18 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $652/Night
7 Nights - US $4,565
Apartment
- Chicago
- ·
- Blue Island
- 0.72 mi to center
8.0Excellent
(1 Review)
5 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Child Friendly
TV
US $280/Night
7 Nights - US $1,958
House
- Chicago
- ·
- Morgan Park
- 0.37 mi to center
5.8Average
(6 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $324/Night
7 Nights - US $2,265
House
- Chicago
- ·
- Morgan Park
- 0.39 mi to center
3 Bedrooms
1 Bath
12 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $295/Night
7 Nights - US $2,064
Apartment
- Chicago
- ·
- Blue Island
- 0.51 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $219/Night
7 Nights - US $1,533
Wheelchair Accessible Vacation Homes in Crestwood
Over 14+ Wheelchair Accessible Vacation Homes in or Near Crestwood
Hotel
- Chicago
- ·
- Calumet Park
- 1.02 mi to center
10.0Exceptional
(1 Review)
8 Baths
259.68 ft²
- Fireplace/Heating
- Breakfast
- Parking
- Air Conditioner
US $89/Night
7 Nights - US $623
Hotel
8.2Excellent
(1160 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
US $124/Night
7 Nights - US $867
Hotel
7.8Very Good
(484 Reviews)
8 Baths
247.57 ft²
- Fireplace/Heating
- Breakfast
- Parking
- Air Conditioner
US $110/Night
7 Nights - US $770
Hotel
- Chicago
- ·
- Orland Hills
- 0.91 mi to center
7.4Very Good
(1001 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $105/Night
7 Nights - US $733
Hotel
- Chicago
- ·
- Orland Hills
- 0.91 mi to center
7.8Very Good
(362 Reviews)
6 Baths
159.66 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $145/Night
7 Nights - US $1,014
Hotel
6.2Good
(178 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
US $96/Night
7 Nights - US $672
Hotel
7.5Very Good
(245 Reviews)
2 Baths
226.04 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $102/Night
7 Nights - US $714
Hotel
6.7Good
(319 Reviews)
7 Baths
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $95/Night
7 Nights - US $667
Hotel
- Chicago
- ·
- Bridgeview
- 1.19 mi to center
6.4Good
(864 Reviews)
8 Baths
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $87/Night
7 Nights - US $607
Crestwood Resorts and Airbnb Homes Under $200
Over 75+ Crestwood Resorts and Airbnb Homes Under $200
Condo
- Chicago
- ·
- Palos Hills
- 1.06 mi to center
5.0Average
(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $104/Night
7 Nights - US $728
Apartment
3 Bedrooms
1 Bath
6 Guests
2195.84 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $145/Night
7 Nights - US $1,015
Hotel
- Chicago
- ·
- Chicago Ridge
- 0.97 mi to center
8.6Fabulous
(100 Reviews)
1 Bath
- Kitchen
- Parking
- Air Conditioner
- Internet
US $97/Night
7 Nights - US $678
New
Apartment
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $178/Night
7 Nights - US $1,243
House
1 Bedroom
1 Bath
3 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $132/Night
7 Nights - US $924
New
Apartment
1 Bedroom
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $166/Night
7 Nights - US $1,161
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $134/Night
7 Nights - US $939
Apartment
- Chicago
- ·
- East Beverly
- 0.33 mi to center
2 Bedrooms
1 Bath
1 Guest
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $127/Night
7 Nights - US $891
Apartment
- Chicago
- ·
- West Pullman
- 0.03 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $111/Night
7 Nights - US $774
Instantly Bookable Vacation Homes in Crestwood
Over 49+ Instantly Bookable Vacation Homes in or Near Crestwood
Apartment
- Chicago
- ·
- Chicago Ridge
- 0.29 mi to center
5.6Average
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $212/Night
7 Nights - US $1,481
House
- Chicago
- ·
- Oak Forest
- 2.04 mi to center
9.2Exceptional
(19 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $316/Night
7 Nights - US $2,209
House
- Chicago
- ·
- Morgan Park
- 0.62 mi to center
4 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $321/Night
7 Nights - US $2,245
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $236/Night
7 Nights - US $1,650
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
US $184/Night
7 Nights - US $1,286
Apartment
3 Bedrooms
1 Bath
6 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $140/Night
7 Nights - US $982
Apartment
3 Bedrooms
2 Baths
6 Guests
1836 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $98/Night
7 Nights - US $686
Cottage
9.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
US $178/Night
7 Nights - US $1,244
House
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $140/Night
7 Nights - US $979
Book a Last Minute Place to Stay in Crestwood
About Crestwood Vacation Rentals
Explore over 173 vacation rentals in Crestwood with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Crestwood for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Crestwood. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Crestwood tailored to your preferences. On average, these rentals offer 316.44 ft² of space, and are priced at an average of US $223 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Crestwood at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Crestwood
| Type | Count |
|---|---|
| Vacation Homes | 82 |
| Holiday Apartments | 35 |
| Cottages | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Crestwood
★ Pro Tip: Discover Your Ideal Vacation Rental in Crestwood with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Crestwood, IL
View the weather forecast for Crestwood before booking your Crestwood Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Crestwood, IL
Sunski offers a large selection of top attractions around Crestwood . Research things to do on your vacation before you visit Crestwood.
Frequently Asked Questions About Crestwood?
What are the top vacation rentals in Crestwood?
When organizing your trip to Crestwood, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Crestwood. Peruse our collection of highly-rated properties and secure your reservation today.
- Executive Family Home in quiet Culdesac
- Charming 3-bedroom apartment in superb Chicago with WiFi
- The Country Life - house
- Thirty Day Minimum Condo in Chicago SW Suburbs of Orland Park Illinois
- Large Space With Garage
- Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
- Charming 2-Bedroom Apt. King Bed, Desk, Fast WiFi, A/C, Near Hospitals
- 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
Which vacation homes or resorts in Crestwood are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Crestwood. Enjoy great views, locations and save money with SunSki Resorts.™
- Clean,Cozy,Convenient -1-bedroom Condo-Malls, Museums, Nature, Chicago, and More
- Country Club Hills Home: Walk to Rec Center!
- GATEWAY INN
How many SunSkiResorts vacation rentals or resorts are available in Crestwood?
Discover the ideal vacation rental in Crestwood with SunSki Resorts™. We provide an extensive selection of over 173 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Crestwood.
People Also Ask
Finding the best prices in Crestwood
Map
