Unplugged Weekend - Vacation Rentals in Sleepy Hollow

In the Heart of Little Mexico! Shared Stylish Apartment in Chicago From US $33
         

Luxury Places to Stay in Sleepy Hollow

Over 125+ Luxury Places to Stay in or Near Sleepy Hollow
Hampton Inn Chicago-Midway Airport From US $1,105
         

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7.9 (359 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 3-bedroom apartment with WiFi, AC in safe area in Cicero IL. From US $559
         

Berwyn FHS Rental From US $395
         

New
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  • Pet Friendly
Extended Stay Berwyn FHS Rental From US $385
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Chicago FHS Rental - Narragansett From US $286
         

New
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Chicago FHS Rental - Narragansett From US $282
         

New
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Near Midway Newly remodeled From US $258
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Sleepy Hollow

Over 14+ Top-Rated Vacation Rentals with a Pool in or Near Sleepy Hollow
DoubleTree by Hilton Chicago Midway Airport From US $163
         

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9.2 (1000 Reviews)
Hotel
  • Air Conditioner
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  • Pool
Hyatt Place Chicago Midway Airport From US $159
         

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9.0 (1216 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn Marriott Chicago Midway From US $169
         

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8.8 (595 Reviews)
Hotel
  • Air Conditioner
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  • Pool
Residence Inn Chicago Midway Airport From US $212
         

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8.8 (88 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
DoubleTree by Hilton Chicago Midway Airport, IL From US $198
         

Hyatt Place Chicago Midway Airport From US $181
         

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8.6 (769 Reviews)
Hotel
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  • Pet Friendly
Hilton Garden Inn Chicago/Midway Airport From US $134
         

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8.4 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Chicago Marriott Midway From US $159
         

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8.4 (919 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Sleepy Hollow

Over 47+ Pet-Friendly Vacation Rentals in or Near Sleepy Hollow
3BR Monthly Rental Near Midway Airport/Downtown From US $236
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Chicago Marriott Midway From US $173
         

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8.2 (166 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 From US $218
         

8.6 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Vintage Arcade Apt with Parking From US $171
         

6.0 (6 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Stylish & Comfy Stay: Close to Downtown From US $99
         

4.0 (1 Review)
House
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  • Pet Friendly
Steps from Midway Airport, 2BR Rental From US $241
         

New
Apartment
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  • Pet Friendly
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Charming 1-bedroom apartment in brilliant Berwyn with AC, WiFi From US $164
         

Large Vacation Homes & Villas in Sleepy Hollow

Over 13+ Large Vacation Homes & Villas in or Near Sleepy Hollow
Chicago FHS Rental - Berwyn Ave From US $233
         

2.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
La Villita - Gateway to Chicago From US $140
         

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8.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Extended Stay- Chicago FHS Rental - W 64th St From US $254
         

Chicago FHS Rental - W 64th St From US $249
         

New
House
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  • Pet Friendly
Berwyn Rental From US $294
         

5.0 (1 Review)
House
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  • Pet Friendly
  • TV
Berwyn Rental From US $347
         

New
House
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Sleepy Hollow

Over 10+ Wheelchair Accessible Vacation Homes in or Near Sleepy Hollow
Holiday Inn Express & Suites Chicago-Midway Airport by IHG From US $177
         

8.3 (299 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Hampton Inn by Hilton Chicago-Midway Airport From US $129
         

8.4 (1260 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Fairfield Inn & Suites Chicago Midway Airport From US $149
         

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8.0 (270 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Fairfield Inn and Suites by Marriott Chicago Midway Airport From US $119
         

Hilton Garden Inn Chicago/Midway Airport From US $172
         

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7.9 (247 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sleep Inn Midway Airport Bedford Park From US $99
         

8.0 (1748 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Sleep Inn Midway Airport From US $116
         

7.7 (661 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard Chicago Midway Airport From US $158
         

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7.7 (212 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly

Sleepy Hollow Varoom and Airbnb Places to Stay Under $200

Over 52+ Sleepy Hollow Varoom and Airbnb Places to Stay Under $200
Condo Apartment Near Midway Airport From US $129
         

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8.9 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Chicago Buddha's Abode From US $156
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy Urban Retreat Near Midway – Perfect for Travelers! From US $162
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP From US $162
         

9.8 (29 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy 2- bedroom w/patio mins from Midway Airport From US $178
         

9.8 (12 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Rustic APT/Near Hosp/25mins to ORD/MDW/DT/Free Parking & WIFI From US $163
         

Instantly Bookable Vacation Homes in Sleepy Hollow

Over 39+ Instantly Bookable Vacation Homes in or Near Sleepy Hollow
Berwyn Beauty From US $221
         

10.0 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Stylish comfortable 3BR with tons of natural light From US $239
         

Ridgeland Retreat/Street level Apt easy access From US $210
         

9.4 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxurious 3Br with parking on premises 🌔 From US $225
         

9.2 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy, Sunny, and Clean Apt 3 bd Free Parking From US $233
         

9.2 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Chic Chicago Retreat (2-Bedroom Home) by RedAwning From US $208
         

8.6 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Sleepy Hollow Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Unpluggedweekend Sleepy Hollow, 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 Sleepy Hollow. Places to stay near Sleepy Hollow are 2100 ft² on average, with prices averaging $33 a night.

Unpluggedweekend makes it easy and safe to find and compare vacation rentals in Sleepy Hollow 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 Sleepy Hollow

Type Count
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Sleepy Hollow

Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend 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 Sleepy Hollow.

Weather in Sleepy Hollow

View the weather forecast for Sleepy Hollow before booking your Sleepy Hollow 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