What is Deep Hole like?

Travelers to the Deep Hole neighborhood in Chincoteague will be sure to enjoy their stay. Consider a visit to Oyster Bay as part of your Deep Hole travel plans.

What's a favorite hotel to stay in Deep Hole?

For your stay in Deep Hole, Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury is one of the top choices based on our traveler data. Other good options for your stay in the area include Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets and The Blue Crab - Your Dream Vacation awaits you! .

How many hotels are there in the Deep Hole area?

Expedia has 80 hotels and other accommodations in Deep Hole to choose from, making this an ideal home base for exploring the greater Chincoteague area.

If I need to cancel my hotel reservation in Deep Hole, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of booking. Enter your dates, click on "Search", then filter by "fully refundable" to review the best deals available in Deep Hole.

What are the top things to see and do in Deep Hole?

Oyster Bay is an attraction you might want to check out while you're in Deep Hole. Captain Timothy Hill House and Maui Jack's Waterpark are also worth a visit when you're out sightseeing in Chincoteague.

Hotels in Deep Hole, Chincoteague

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Dates

March 2026

3

April 2026

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Our top choices for Deep Hole hotels

Key West Cottages

Downtown Chincoteague, 1.9 km from Deep Hole

CHRISTIE

Spark by Hilton Chincoteague Island

Piney Island, 1.6 km from Deep Hole

Mary

CA $125 total

includes taxes & fees

Mar 13 - Mar 14

Waterside Inn

Downtown Chincoteague, 2.9 km from Deep Hole

Michael

Refuge Inn

Piney Island, 1.5 km from Deep Hole

Paul

CA $140 total

includes taxes & fees

Mar 15 - Mar 16

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Downtown Chincoteague, 2.5 km from Deep Hole

Edward

CA $178 total

includes taxes & fees

Mar 19 - Mar 20

Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague, 1.9 km from Deep Hole

Tim

CA $156 total

includes taxes & fees

Mar 22 - Mar 23

Island Resort

Downtown Chincoteague, 1.7 km from Deep Hole

Anna

CA $214 total

includes taxes & fees

Mar 18 - Mar 19

Best Western Plus Pocomoke City

23.6 km from Deep Hole

Brittany

CA $148 total

includes taxes & fees

Mar 18 - Mar 19

Hampton Inn & Suites Chincoteague Waterfront

Downtown Chincoteague, 2 km from Deep Hole

William

CA $173 total

includes taxes & fees

Mar 25 - Mar 26

Days Inn by Wyndham Chincoteague Island

Piney Island, 1.4 km from Deep Hole

Elizabeth

CA $89 total

includes taxes & fees

Mar 13 - Mar 14

Studio 6 Suites Pocomoke City, MD

21 km from Deep Hole

Jennifer

CA $115 total

includes taxes & fees

Mar 5 - Mar 6

Garden and Sea Inn

16.4 km from Deep Hole

Angela

CA $270 total

includes taxes & fees

Mar 4 - Mar 5

Birchwood Inn

Downtown Chincoteague, 3.2 km from Deep Hole

Zariyah

CA $96 total

includes taxes & fees

Mar 19 - Mar 20

Anchor Inn

Downtown Chincoteague, 2.8 km from Deep Hole

Anonymous traveller

CA $109 total

includes taxes & fees

Mar 19 - Mar 20

Atlantic Shores Inn and Suites

Downtown Chincoteague, 1.3 km from Deep Hole

Barbara

CA $123 total

includes taxes & fees

Mar 18 - Mar 19

Marina Bay Hotel & Suites, an Ascend Collection Hotel

Downtown Chincoteague, 2.8 km from Deep Hole

Katherine

CA $136 total

includes taxes & fees

Mar 23 - Mar 24

Chincoteague Inn

Downtown Chincoteague, 1.2 km from Deep Hole

Korey E

CA $129 total

includes taxes & fees

Apr 2 - Apr 3

Econo Lodge Pocomoke City Hwy 13

19.5 km from Deep Hole

Luisa

CA $116 total

includes taxes & fees

Mar 19 - Mar 20

Motel 6 Pocomoke City, MD

21 km from Deep Hole

Zarah

CA $107 total

includes taxes & fees

Mar 19 - Mar 20

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Where to stay in Deep Hole

Find the best Deep Hole areas and neighborhoods for the activities you enjoy most.

Downtown Chincoteague

While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.

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Piney Island

While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.

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Snotty Ridge

While there might not be top attractions in Snotty Ridge, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.

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Down the Marsh

If you're looking for some top things to see and do in Down the Marsh and surrounding area, you can visit Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.

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Up the Neck

If you're looking for some top things to see and do in Up the Neck and surrounding area, you can visit Oyster Bay and Captain Timothy Hill House.

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Top Deep Hole Hotel Reviews

Best Western Plus Pocomoke City

8/10 Good

"Everything was great, except for the lighting in the room. The lamps on the bedside are very low lit, and the shade around them cast a yellow light. The other lights are very bright and harsh. Thanks."