Owner Direct Vacation Rentals in Crestwood

The Best Owner Direct Vacation Rentals in Crestwood. Explore thousands of vacation home rentals, large cabins, and villas near Crestwood

Comfortable & Relaxing Charming 3BR unit From US $213
         

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8.2 (5 Reviews)
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  • Pet Friendly
Holiday Inn Express & Suites Chicago - Oak Forest by IHG From US $115
         

Oak Lawn Apartment about 2 Mi to Ford City Mall! From US $145
         

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Luxury Retreat Near Local Gems From US $225
         

New
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Days Inn by Wyndham Calumet Park From US $89
         

10.0 (1 Review)
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  • Wheelchair Accessible

Luxury Places to Stay in Crestwood

Over 152+ Luxury Places to Stay in or Near Crestwood
Suburban Feel with a City Vibe From US $652
         

9.6 (4 Reviews)
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Delightful 4-bedroom house with AC in Tinley Park From US $489
         

9.4 (3 Reviews)
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Crestwood FHS Rental - #1 From US $464
         

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Extended Stay - Crestwood FHS Rental From US $397
         

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Large Space With Garage From US $393
         

10.0 (1 Review)
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The Country Life - house From US $358
         

10.0 (3 Reviews)
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*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi From US $338
         

9.6 (55 Reviews)
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Crestwood

Over 10+ Top-Rated Vacation Rentals with a Pool in or Near Crestwood
Hilton Chicago/Oak Lawn From US $131
         

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8.4 (1178 Reviews)
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DoubleTree by Hilton Chicago - Alsip From US $110
         

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8.4 (1011 Reviews)
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Holiday Inn Express & Suites Chicago - Oak Forest by IHG From US $117
         

8.3 (218 Reviews)
Hotel
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  • Pool
  • Private Pool
Hilton Chicago/Oak Lawn From US $174
         

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8.1 (569 Reviews)
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DoubleTree by Hilton Chicago/Alsip From US $201
         

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7.9 (264 Reviews)
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Holiday Inn Express Crestwood by IHG From US $97
         

7.8 (1005 Reviews)
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Spark by Hilton Oak Forest From US $100
         

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7.8 (55 Reviews)
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Holiday Inn Express Crestwood by IHG From US $126
         

7.5 (181 Reviews)
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  • Pool

Pet-Friendly Vacation Rentals in Crestwood

Over 50+ Pet-Friendly Vacation Rentals in or Near Crestwood
Quality Inn & Suites Orland Park - Chicago From US $107
         

7.1 (384 Reviews)
Hotel
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  • Pet Friendly
Red Roof Inn Chicago - Alsip From US $72
         

6.0 (628 Reviews)
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Motel 6-Alsip, IL From US $94
         

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6.8 (328 Reviews)
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  • Pet Friendly
  • Wheelchair Accessible
Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community From US $137
         

Motel 6-Bridgeview, IL From US $87
         

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6.3 (835 Reviews)
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Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community From US $137
         

9.0 (28 Reviews)
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Red Roof Inn Chicago-Alsip From US $84
         

4.7 (117 Reviews)
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Large Vacation Homes & Villas in Crestwood

Over 16+ Large Vacation Homes & Villas in or Near Crestwood
Executive Family Home in quiet Culdesac From US $232
         

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10.0 (5 Reviews)
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Charming 2-bedroom apartment in marvelous Blue Island with WiFi From US $200
         

7.6 (4 Reviews)
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Relaxing hot and beautiful 4 bed, 2 baths in peaceful area From US $324
         

5.8 (6 Reviews)
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  • Pet Friendly
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Relaxing, peaceful and quiet. 4 bedroomnn From US $295
         

Markham Retreat Near Parks ~ 24 Mi to Chicago! From US $286
         

9.8 (17 Reviews)
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Luxury Home Fenced in Yard Palos From US $340
         

8.0 (3 Reviews)
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  • Pet Friendly
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Wheelchair Accessible Vacation Homes in Crestwood

Over 11+ Wheelchair Accessible Vacation Homes in or Near Crestwood
Baymont by Wyndham Chicago/Alsip From US $110
         

7.8 (484 Reviews)
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Baymont by Wyndham Chicago/Alsip From US $109
         

8.2 (1005 Reviews)
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Gateway Inn Oaklawn-Chicago Midway airport From US $102
         

7.8 (262 Reviews)
Hotel
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  • View
Quality Inn & Suites Orland Park - Chicago From US $94
         

7.4 (1000 Reviews)
Hotel
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The Best Inn & Suites From US $80
         

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6.2 (266 Reviews)
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Motel 6 Bridgeview, IL From US $48
         

7.2 (1355 Reviews)
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Bridgeview Inn Chicago Area From US $106
         

5.7 (154 Reviews)
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The Best Inn & Suites From US $90
         

6.2 (165 Reviews)
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Crestwood Varoom and Airbnb Places to Stay Under $200

Over 66+ Crestwood Varoom and Airbnb Places to Stay Under $200
Blue Star Motel From US $65
         

8.0 (42 Reviews)
Hotel
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“The cottage” 2 bedrooms cozy and private home From US $178
         

9.0 (9 Reviews)
Cottage
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GATEWAY INN From US $106
         

8.4 (151 Reviews)
Hotel
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Hotel O Miami Inn & Suites Chicago Midway Airport From US $59
         

6.1 (392 Reviews)
Hotel
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In Chicago, Near Beverly & Evergreen Park Home From US $185
         

9.0 (2 Reviews)
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Midway Inn & Suites From US $66
         

5.8 (236 Reviews)
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Comfy 2 bedroom condo with 75” smart TV From US $190
         

5.6 (5 Reviews)
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Luxe Motel From US $75
         

5.2 (4 Reviews)
Hotel
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Instantly Bookable Vacation Homes in Crestwood

Over 44+ Instantly Bookable Vacation Homes in or Near Crestwood
~Home Comforts, Roku SmartTV, Fast WiFi~ From US $148
         

Suns & Roses Duplex From US $117
         

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Relax & Unwind in This Comfortable 3BR Unitn From US $147
         

10.0 (5 Reviews)
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Charming 3-bedroom apartment in superb Chicago with WiFi From US $194
         

10.0 (3 Reviews)
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Private Home Awaits From US $271
         

9.2 (10 Reviews)
House
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  • Pet Friendly

About Crestwood Vacation Rentals

With more than 161 Crestwood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Crestwood.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Crestwood, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Crestwood. Places to stay near Crestwood are 329.98 ft² on average, with prices averaging $205 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Crestwood with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Crestwood

Type Count
Vacation Homes 75
Hotels with Suites 43
Holiday Apartments 32
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Crestwood

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Crestwood.

Weather in Crestwood

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

Complexes around Crestwood, IL