Discover Your Perfect Sleepy Hollow Vacation Homes

Best Vacation Homes in Sleepy Hollow

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Sleepy Hollow Luxury Rentals

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Sleepy Hollow Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Sleepy Hollow Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Sleepy Hollow Vacation Rentals

Where are the best neighborhoods to stay in Sleepy Hollow?

When exploring Sleepy Hollow in San Anselmo, California, you’ll find that the neighborhood offers a charming and peaceful setting perfect for a relaxing getaway. Its scenic surroundings and welcoming atmosphere make it an ideal choice for those seeking a serene retreat within close proximity to local amenities. Staying in this area gives you easy access to the natural beauty and community charm that define San Anselmo, ensuring a comfortable and memorable stay. Whether you prefer cozy homes or stylish accommodations, Sleepy Hollow provides a variety of options to suit your needs, making it a top choice for your next visit to the region.

Oak Manor

Located within a peaceful enclave, Oak Manor offers a serene escape where you can enjoy the tranquil surroundings of this region. It’s an ideal choice for those seeking comfort and convenience while exploring the charming area nearby.

View 95+ Rentals in Oak Manor

Best Times to Visit Sleepy Hollow

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here can enhance your experience, as the best seasons for visiting Sleepy Hollow in San Anselmo often depend on your preferences for weather and local events throughout the year.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area blossoms with mild temperatures and vibrant scenery, making it an ideal time for exploring- a perfect season to enjoy the local charm.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 50°F to 55°F
autumn
Fall (September to November)

Autumn brings cooler weather and colorful foliage, offering a cozy atmosphere that enhances your stay in this scenic destination.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

Winter months feature cooler temperatures and less tourist activity, providing a peaceful retreat for those seeking tranquility in the region.

Average Temperature Daytime: 55°F to 60°F - Nighttime: 40°F to 45°F
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Summer (June to August)

While summer offers warm days, it is also the least crowded time, allowing you to enjoy the serene environment at a relaxed pace.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 60°F

Weekly Weather Forecast for Sleepy Hollow

How to Book Your Sleepy Hollow 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 Sleepy Hollow

More Top-Rated Vacation Rentals in Sleepy Hollow Area

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 a private outdoor patio or deck, perfect for relaxing and taking in the scenic surroundings.
  • Take advantage of a well-maintained garden area to explore local flora or unwind amidst nature.
  • Make use of outdoor seating areas for dining al fresco with views of the region's beautiful landscape.
  • Access a spacious backyard ideal for outdoor activities or family gatherings during your stay.
  • Benefit from a fire pit or outdoor fireplace to enjoy cozy evenings under the stars.
  • Utilize available outdoor grilling facilities to prepare meals while soaking in the peaceful atmosphere.
  • Discover nearby walking trails or hiking paths that allow you to explore the natural beauty of this destination.

Top Attractions Around Sleepy Hollow

What attractions are nearby?

In this charming area, you can enjoy strolling through scenic parks, exploring local hiking trails, and discovering peaceful spots perfect for relaxation and outdoor activities.

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Family Activities

  • Sleepy Hollow Trail Walks: Embark on scenic walking trails that offer families a chance to enjoy the natural beauty and tranquility of the region.
  • Local History Tours: Discover the rich history of the area through guided tours that highlight its unique cultural heritage and folklore.
  • Family-Friendly Parks: Spend quality time at nearby parks that feature playgrounds, picnicking areas, and open spaces perfect for outdoor activities.
  • Community Events and Festivals: Participate in seasonal events hosted here, providing entertainment and engaging experiences for visitors of all ages.
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Adult Activities

  • Hiking and Nature Walks: Explore scenic trails in nearby parks that offer serene outdoor experiences amidst the region's lush landscapes.
  • Visit Local Wineries: Indulge in wine tasting tours at the area's renowned wineries, perfect for relaxing and enjoying the region’s viticulture.
  • Historic Downtown Tours: Discover charming boutiques, cafes, and cultural landmarks by strolling through the historic downtown area.
  • Art Galleries and Cultural Events: Immerse yourself in the local arts scene with visits to galleries and participation in seasonal cultural festivals held locally.

Sleepy Hollow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Natural Beauty: Take advantage of the nearby parks and scenic trails to immerse yourself in the region's stunning landscapes and enjoy outdoor activities that showcase the area's natural charm.
  • Visit Charming Community Events: Check out local markets, festivals, or seasonal gatherings to experience the authentic culture and friendly atmosphere of this destination.
  • Discover Unique Dining Options: Sample farm-to-table cuisine and cozy cafes that highlight the region’s fresh ingredients and inviting hospitality, adding a special touch to your stay.
  • Plan Thoughtful Excursions: Use your vacation rentals as a comfortable base while exploring nearby attractions, historical sites, or hidden gems that make your visit memorable.

Transportation Options

  • Car Rentals: Renting a car provides the flexibility to explore the scenic surroundings of this charming area at your own pace, with numerous rental agencies available nearby.
  • Public Transit: The regional transit system offers convenient bus services that connect you to San Francisco and other key locations in the region, making it easy to navigate without a private vehicle.
  • Taxi and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft operate here, offering quick and reliable transportation for local travel or trips farther afield.
  • Bicycle Rentals: For those seeking an eco-friendly and active way to discover the area’s natural beauty, bicycle rentals are readily accessible, allowing you to enjoy outdoor adventures on your schedule.

Local Customs Options

  • Traditional Fall Celebrations: Participating in seasonal festivities here offers a glimpse into the local community's cherished customs during autumn.
  • Historic Halloween Events: Engaging in themed activities around October allows visitors to experience this area's unique approach to festive traditions.
  • Community Art Celebrations: Local art displays and craft fairs reflect the region's appreciation for creativity and cultural expression.
  • Dining Etiquette and Local Cuisine: Savoring regional flavors at nearby eateries provides insight into the culinary traditions valued by residents.

Sleepy Hollow Vacation Rental Frequently Asked Questions

1. 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:

2. How many vacation rentals have private pools in Sleepy Hollow?

There are 6 vacation rentals with private pools near Sleepy Hollow. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

4. How many Rentbyowner vacation rentals are available in Sleepy Hollow?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 120 in the Sleepy Hollow 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 Sleepy Hollow. 

5. What is the cancellation policy for vacation rentals in Sleepy Hollow, San Anselmo?

Cancellation policies vary depending on the individual property listing. To ensure you understand the specific terms, please review the cancellation details provided in the listing before booking or contact the property owner directly.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing. It's recommended to read the full details or communicate with the host to clarify all costs involved.

7. How do I verify the safety and reliability of vacation rentals in this area?

All listings undergo verification processes, but you can also read reviews from previous guests and reach out directly to hosts to ask questions about safety measures and property conditions to ensure a trustworthy stay.

8. What amenities are generally included in vacation rentals in this region?

Amenities vary by property, but common features include Wi-Fi, fully equipped kitchens, parking, and outdoor spaces. Specific amenities are detailed on each listing; reviewing these will help you find a property that meets your needs.

9. How do I ensure my booking is secure when reserving a vacation rental here?

Secure booking is facilitated through trusted platforms that provide secure payment options. For added peace of mind, verify the host’s profile, read reviews, and follow the platform’s guidelines for safe transactions.