Deep Hole holiday homes

We found 672 holiday rentals — enter your dates for availability

Discover a selection of 82 homes and other holiday rentals in Deep Hole that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Deep Hole

Showing deals for:18 Jul - 25 Jul

Image gallery for "A Gem By The Sea" for your family.

Plenty private parking** * PLEASE NO PARKING/DRIVING on this field area***
9.6 out of 10 rating
Exceptional
(68 reviews)

"A Gem By The Sea" for your family.

Chincoteague, VA

16% off
Price is NZ$2,364
NZ$338 per night
includes taxes & fees
"A Gem By The Sea" for your family.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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)
  • Assateague Point (3.5 mi / 5.6 km)
  • Chincoteague Channel (4 mi / 6.4 km)
  • Pocomoke River State Park (14.8 mi / 23.8 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 most popular type of holiday home accommodation in Deep Hole?
According to our data, houses are the most sought-after property type in Deep Hole. But that goes without saying, everyone’s idea of the perfect stay can differ. Bookabach has holiday homes of all sizes and shapes, so you’re bound to find your ideal fit.
How much does it cost to rent a holiday home in Deep Hole?
Season, length of stay and property type are some things that can influence the price of a holiday home. Simply add your dates of travel to find your perfect fit. From cosy chalets to plush villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Deep Hole?
The average price for a holiday home by the beach in Deep Hole depends on when you’re travelling and the type and size of property you want. You can find prices easily and quickly on Bookabach by entering your travel dates. Then use our handy filter tool to pick the number of bedrooms and amenities essential to you, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Deep Hole?
With 54 holiday homes that welcome four-legged guests, your furry little friend can join you on your Deep Hole holiday. Use our filter tool to search our pet-friendly holiday homes and find a stay that’ll set tails wagging on Bookabach.
Can I rent a house with a pool in Deep Hole?
Tick the “pool” box in our handy filter tool and take your pick of two houses with private pools in Deep Hole on Bookabach. Ball games, gentle soak or noodle joust? Downtime is up to you when your Bookabach holiday home has its own swimming pool.
What are popular home amenities in Deep Hole?
A nearby waterfront, a garden and a swimming pool rank as the most popular home amenities in Deep Hole. Whether you’re planning to travel solo, with your significant other or a group of friends, Bookabach will help you find a holiday home that matches your style with all the extras you’re looking for.
Are there large group holiday homes in Deep Hole?
Deep Hole has 10 holiday properties that can accommodate 10 or more people. These stays come with the privacy and space you need to share good times with family and friends.
Are there holiday homes in Deep Hole that welcome kids?
Gather your whole crew for a fun-packed adventure in Deep Hole at one of our 46 family-friendly properties. Many of these stays provide conveniences that are ideal for trips with the kids, such as dining rooms, living rooms and outdoor spaces. Just click on the “Properties good for families” filter and pick your favourite option.
What are the top attractions for families in Deep Hole?
Keeping the kids amused during your stay in Deep Hole is a cinch with these exciting family-friendly attractions:

  • Maui Jacks Waterpark
  • Robert N. Reed Downtown Waterfront Park
  • Oyster Bay

Can I find two-bedroom holiday homes in Deep Hole?
Gather your loved ones and relax in total privacy and comfort in one of the nine two-bedroom holiday properties Deep Hole has to offer.
Are there holiday homes with WiFi in Deep Hole?
Whether you’d like to keep up with world events, reply to emails or surf social media, there are six holiday homes with WiFi in Deep Hole. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Deep Hole?
Pick your dates and then use our filter tool to see holiday homes with ac in Deep Hole on Bookabach. With 37 air-conditioned properties available, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday home in Deep Hole?
We recommend checking with the Deep Hole holiday property you want on Bookabach as age restrictions vary. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Deep Hole for?
The amount of time you can rent a Deep Hole holiday home for varies depending on the property. Simply tap in your dates of travel to browse options offering extended stays. They have all you need to make your extended holiday more enjoyable and convenient, like air conditioning and kitchens. Some Bookabach holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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