Deep Hole holiday lettings

We found 301 holiday rentals — enter your dates for availability

Discover a selection of 79 homes and other holiday rentals in Deep Hole that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a hot tub. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Choose a holiday rental for your Deep Hole getaway

Learn about the unique charm of Deep Hole with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Deep Hole

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that Deep Hole has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Maui Jack's Waterpark (0.8 mi / 1.3 km)
  • Captain's Cove Golf and Yacht Club (5.5 mi / 8.8 km)
  • Nassawango Golf Course (15.6 mi / 25.1 km)

Exploring the natural features in Deep Hole

Whether you're an active traveller or just want to take in the scenery, Deep Hole is a great place to get outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Oyster Bay (1.1 mi / 1.8 km)
  • Robert N. Reed Downtown Waterfront Park (1.4 mi / 2.2 km)
  • Chincoteague National Wildlife Refuge (1.6 mi / 2.6 km)
  • Thurf Marsh Islands (2.6 mi / 4.2 km)
  • Assateague Point (3.5 mi / 5.6 km)
  • Chincoteague Channel (4 mi / 6.4 km)

Transport options to and around Deep Hole

The nearest airport is in Ocean City, MD (OCE-Ocean City Municipal), located 28.7 mi (46.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 29.4 mi (47.3 km) away.

Frequently asked questions

What is the best area to stay in Deep Hole when booking a holiday rental?
When considering a holiday rental in Deep Hole, Virginia, the best area to stay in would be near the scenic surroundings of the Appalachian Mountains. This region offers a charming blend of natural beauty and outdoor activities, making it an ideal choice for nature enthusiasts and those seeking a peaceful retreat.

One popular neighbourhood to consider is around the banks of the nearby rivers and streams, which provide opportunities for fishing, kayaking, and hiking. Staying in this area allows you easy access to the stunning landscapes, with trails that lead to breathtaking vistas and serene picnic spots. One of the top attractions nearby is the Natural Bridge State Park, known for its impressive natural rock formation and beautiful hiking trails. The park is a wonderful place for both leisurely walks and more challenging hikes, suiting all levels of outdoor adventurers.

Another appealing aspect of this area is the proximity to local cultural sites, such as historic landmarks and small museums that celebrate the rich history of Virginia. Visitors can engage in the region's heritage while enjoying the warm hospitality of the local community.
How much does it cost to rent a holiday home in Deep Hole?
Prices for holiday rentals in Deep Hole 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Deep Hole to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Deep Hole holiday house rentals?
You can find great discounts on house rentals in Deep Hole 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.
Can I find long-stay holiday rentals in Deep Hole?
A long-stay holiday rental in Deep Hole 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.
Are there any Deep Hole holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Deep Hole 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.
How early should I book a Deep Hole holiday rental?
Book your Deep Hole holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Deep Hole home rental booking on Vrbo?
To find Deep Hole holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Deep Hole holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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