Chicago\92s Best Vacation Rentals - Vacation Rentals in Sleepy Hollow
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Luxury Places to Stay in Sleepy Hollow
- Air Conditioner
- Parking
- Pool
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- Security/Safety
Top-Rated Vacation Rentals with a Pool in Sleepy Hollow
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
Pet-Friendly Vacation Rentals in Sleepy Hollow
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Large Vacation Homes & Villas in Sleepy Hollow
- TV
- Balcony/Terrace
- Security/Safety
- TV
- Balcony/Terrace
- Security/Safety
- Parking
- Pool
- Designated Smoking Area
- TV
- Balcony/Terrace
- Security/Safety
- Parking
- TV
- Balcony/Terrace
- View
- Ocean View
- Balcony/Terrace
Wheelchair Accessible Vacation Homes in Sleepy Hollow
Sleepy Hollow Vacation Rentals and Airbnb Places to Stay Under $200
- Parking
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- TV
- Balcony/Terrace
- TV
- Balcony/Terrace
- Security/Safety
Instantly Bookable Vacation Homes in Sleepy Hollow
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- TV
- Security/Safety
- Parking
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Designated Smoking Area
About Sleepy Hollow Vacation Rentals
With more than 137 Sleepy Hollow vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals 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 Sleepy Hollow.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals 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 636.02 ft² on average, with prices averaging US $468 a night.
Chicagosbestvacationrentals 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 |
|---|---|
| Vacation Homes | 87 |
| Holiday Apartments | 31 |
| Cottages | 9 |
| Hotels | 6 |
| Villas | 2 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Sleepy Hollow
★ Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals 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.
Sleepy Hollow Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Sleepy Hollow?
There are a lot of options in Sleepy Hollow. If you plan on staying in the Sleepy Hollow area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sleepy Hollow:
- Relax in Fairfax quiet cottage in the redwoods.
- Amazing views, multi-level decks, full kitchen and pool.
- Mountain View Retreat
- Luxury Napa Retreat – Mid-Century Style, Quiet & Prime Location
- Amazing270°Views! 7BR+Loft, Sleeps 19! 15m to SF, GGB or Napa. Central location!
- Luxury Suite w/Views – Spacious, Quiet, Prime Location
- 20 Mins to SF or 20 mins to 1st wine tasting. ALL 23 RATINGS ARE 5 STARS
- Light filled, tree house, surrounded by nature. 7 minute walk from downtown.
- Modern Oasis in San Anselmo - Stunning Views & Ultimate Privacy
- Downtown on Dominga! STEPS to anywhere in Fairfax
How many vacation rentals have private pools in Sleepy Hollow?
There are 5 vacation rentals with private pools near Sleepy Hollow. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Sleepy Hollow are best for families?
If you are looking for a family-friendly vacation home in Sleepy Hollow, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sleepy Hollow:
How many vacation rentals are available in Sleepy Hollow?
Currently, the total number of properties listed in 2026 is over 137 in the Sleepy Hollow area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sleepy Hollow.
