Sleepy Hollow vacation rentals

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August 2025

September 2025

Discover a selection of 8 cabins and other vacation rentals in Sleepy Hollow that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, which might include WiFi and a fireplace. No matter what you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Sleepy Hollow

Showing deals for:Nov 14 - Nov 21

Exceptional

(14 reviews)

Stylish Retreat w Fireplace, Games & Pool Access

Hedgesville, WV

9% off

includes taxes & fees

Exceptional

(228 reviews)

Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities

Hedgesville, WV

10% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Sleepy Hollow

Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals - Sleepy Hollow

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Geocaching Getaway

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Enjoy full kitchens, laundry, pools, yards and more
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Find out more about Sleepy Hollow

Why visit Sleepy Hollow

Stunning natural scenery: Sleepy Hollow boasts breathtaking landscapes ideal for outdoor activities and relaxation.
Thrilling adventures: Engage in various outdoor pursuits, including skiing and hiking, catering to all adventure seekers.
Cultural experiences: Explore local galleries and historical sites, enriching your visit with cultural insights.
Family-friendly activities: Enjoy a range of attractions suitable for all ages, ensuring memorable family moments.
Charming accommodations: Choose from cozy cabins and charming cottages for a comfortable stay in this picturesque location.

Popular types of accommodation around Sleepy Hollow

Planning a getaway to Sleepy Hollow? You're in for a treat! Discover the charm of this picturesque location with a range of vacation rentals including houses, cozy cabins, and charming cottages. Whether you're seeking the best Sleepy Hollow cottage rentals or a welcoming holiday home, we provide transparent information to help you find the perfect spot for your stay. Enjoy savings and reassurance as you explore the beauty of Sleepy Hollow!

Houses: The top choice for visitors in Sleepy Hollow, offering spacious and comfortable stays for families and groups.
Cabins: A close second, these rustic retreats provide a cozy atmosphere surrounded by nature.
Cottages: Quaint and charming, cottages are perfect for a romantic getaway or a peaceful solo retreat.
Chalets: These alpine-inspired lodgings offer a unique, scenic escape for travellers seeking a mountain vibe.
Apartments: Ideal for those looking for convenient and modern living spaces in the heart of Sleepy Hollow.**

Top attractions around Sleepy Hollow

Sleepy Hollow in Hedgesville, West Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Visitors can explore national and urban parks and local galleries, catering to those seeking cultural experiences and family-friendly activities. A trip to Sleepy Hollow promises memorable moments and a chance to connect with nature while enjoying the charm of this unique destination.

Berkeley Springs State Park: This urban park, located 11.3km from Sleepy Hollow, is known for its relaxing atmosphere and family-friendly activities. Enjoy natural mineral springs, walking paths, and a charming town vibe.
Fort Frederick State Park: Situated 8.0km away, this historic fort offers a glimpse into the past with its preserved structures. It's a cultural hub showcasing the area's rich history.
Cacapon Resort State Park: Located 20.9km from Sleepy Hollow, this national park is perfect for adventure seekers. Explore stunning scenery, hiking trails, and outdoor activities amidst nature.

Things to do recommended for couples

For a romantic getaway in Sleepy Hollow, indulge in relaxation at Colonial Springs Spa or Atasia Spa, both offering serene treatments nearby. For a delightful evening, visit Knob Hall Winery, where you can enjoy wine tasting in a charming setting, perfect for couples seeking romance and entertainment.

Things to do recommended for families

Your family will have a fantastic time at the Morgan County Observatory, located 16.1km from Sleepy Hollow. Explore the stars together in a friendly atmosphere, making it a memorable experience for all ages.

Things to do recommended for groups

Explore the Berkeley Springs Antique Mall for unique finds, enjoy shopping and family entertainment at Martinsburg Mall, or immerse yourselves in culture and romance at the Apollo Civic Theatre—all within a short drive from Sleepy Hollow for a memorable group getaway.

What do I need to keep in mind when booking a vacation around Sleepy Hollow

When planning your trip, whether you're travelling with a group, family, pets, or seeking longer accommodations, it's important to filter your options based on your priorities. Here are some helpful Vrbo booking tips to assist you.

Traveling to Sleepy Hollow with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
Traveling to Sleepy Hollow with young kids: Traveling with young children can present some challenges. It’s important to prioritize their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Sleepy Hollow: For many families, a vacation feels incomplete without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels comfortable and at home.
Planning for a long term stay visiting Sleepy Hollow: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Sleepy Hollow

Sleepy Hollow, Hedgesville, offers a perfect getaway for outdoor enthusiasts and families alike. Explore the stunning natural scenery, engage in thrilling adventures, or enjoy romantic getaways by the waterfront. With nearby skiing options, you'll find plenty of activities to keep everyone entertained. The area's historical charm and friendly atmosphere make it an ideal destination for creating lasting memories. Discover the beauty and adventure that await you in and around this hidden gem.

Berkeley Springs: Berkeley Springs is a charming city located 11.3km from Sleepy Hollow, renowned for its natural mineral springs and holistic wellness offerings. Visitors flock here for outdoor adventures and the beautiful scenery that surrounds them. Popular activities in the area include hiking in the nearby national state park and enjoying the recreational areas. Golf enthusiasts will appreciate the local golf course, while winter sports lovers can hit the slopes at local ski venues. The picturesque lake serves as a perfect backdrop for relaxation and recreation.
The Woods: Just 3.2km from Sleepy Hollow, The Woods is a scenic neighbourhood that embodies the spirit of outdoor adventure. This area is perfect for those looking to immerse themselves in nature, with a variety of recreational areas and ski resorts to explore. Visitors can enjoy activities such as skiing and snowboarding during the winter months, while the beautiful lake and national state park offer ample opportunities for hiking and picnicking in warmer weather. The Woods provides a serene escape with its lush landscapes and recreational possibilities.
Cherry Run: Located 6.4km from Sleepy Hollow, Cherry Run is a quaint village that attracts adventurers seeking outdoor thrills and winter sports. Known for its proximity to excellent ski resorts, Cherry Run also features a golf course and scenic trails. The village is surrounded by natural beauty, including a charming canal and the flowing river, which provide a stunning setting for outdoor activities. With its welcoming atmosphere, Cherry Run is ideal for those looking to experience both adventure and relaxation in a picturesque environment.

Best time to go to Sleepy Hollow

If you're planning a trip to Sleepy Hollow, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July to August and October, while off-peak times, like January to March tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.5°F (-0.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
February	34.5°F (1.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	42.4°F (5.8°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
April	53.1°F (11.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
May	62.8°F (17.1°C)	Light Rain	Mostly Sunny	Average	Average
June	71.2°F (21.8°C)	Light Rain	Mostly Sunny	Average	Average
July	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	74.3°F (23.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Average
October	56.1°F (13.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
November	43.9°F (6.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
December	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? One effective strategy is to be flexible with your travel dates, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides an excellent platform for you to plan new adventures, refine your existing itineraries, or manage your reservations with ease. Your saved and booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for your convenience. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Sleepy Hollow?

In Sleepy Hollow, cabins are a popular choice among vacation rentals, with several available throughout the area. These charming properties provide a rustic atmosphere, often featuring wooden interiors, outdoor fire pits, and scenic views of the surrounding nature. Many cabins come equipped with essential amenities like fully stocked kitchens, comfortable living spaces, and sometimes even hot tubs for relaxation after a day of exploring.

How much does it cost to rent a vacation home in Sleepy Hollow?

Prices for vacation rentals in Sleepy Hollow vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sleepy Hollow to more spacious homes.

Are there any discounts for Sleepy Hollow vacation house rentals?

You can find great discounts on house rentals in Sleepy Hollow on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Are there any Sleepy Hollow vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Sleepy Hollow with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

Can I find long-stay vacation rentals in Sleepy Hollow?

A long-stay vacation rental in Sleepy Hollow is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

When is the best time to visit Sleepy Hollow for a vacation rental?

The best time to visit Sleepy Hollow for a vacation rental is during the peak season from March to May. This vibrant period attracts travellers keen to immerse themselves in the natural beauty and charm of West Virginia as spring unfolds. With temperatures typically ranging from 10 to 20 degrees Celsius, the milder weather creates ideal conditions for outdoor activities such as hiking, exploring the lush landscapes, and enjoying the scenic views.

March, in particular, is a popular month to visit Sleepy Hollow, as it marks the beginning of the blossoming season. Visitors can revel in the sight of wildflowers blooming and the awakening of local wildlife, making it a great time for photography and leisurely strolls. The area also hosts various community events that celebrate the arrival of spring, adding to the lively atmosphere.

For those who prefer a more budget-conscious option, consider visiting in December. While this is a quieter time with fewer tourists, it offers a great experience of the picturesque winter landscape, great for cosy retreats and peaceful getaways.

Are there any remote work vacation rentals in Sleepy Hollow?

In Sleepy Hollow, West Virginia, there are several remote work vacation rentals available, with about 11 options for travellers seeking a productive getaway. The area provides a serene environment, superb for focusing on work while enjoying the natural beauty of the surrounding mountains and forests. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs, ensuring that remote workers have everything they need for a successful stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

How early should I book a Sleepy Hollow vacation rental?

Book your Sleepy Hollow vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Sleepy Hollow home rental booking on Vrbo?

To find Sleepy Hollow vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Sleepy Hollow vacation rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.