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.

How many hotels are there in the Deep Hole area?

Expedia has 92 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.

Where can I learn more about changing or cancelling my trip to Deep Hole?

For additional details about changing or cancelling your trip to Deep Hole, click here .

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.

Top Deep Hole Hotels

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Our top choices for Deep Hole hotels

A waterfront hotel with multiple balconies, a dock, and a calm water body.

1. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Downtown Chincoteague, 2.5 km from Deep Hole

Stephanie Lynn

₩179,118 total

includes taxes & fees

Oct 25 - Oct 26

A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.

2. Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague, 1.9 km from Deep Hole

Marc

₩180,661 total

includes taxes & fees

Oct 25 - Oct 26

A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.

3. Hampton Inn & Suites Chincoteague Waterfront

Downtown Chincoteague, 2 km from Deep Hole

Karen

₩153,051 total

includes taxes & fees

Nov 2 - Nov 3

A multi-story hotel with a blue roof, located near a marina with boats docked.

4. Marina Bay Hotel & Suites, an Ascend Collection Hotel

Downtown Chincoteague, 2.8 km from Deep Hole

James

₩146,769 total

includes taxes & fees

Oct 25 - Oct 26

A waterfront house with a balcony, dock, and a view of the water.

5. Key West Cottages

Downtown Chincoteague, 1.9 km from Deep Hole

Debra

₩291,391 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with lounge chairs and a beach ball.

6. Refuge Inn

Piney Island, 1.5 km from Deep Hole

Joe

₩204,255 total

includes taxes & fees

Nov 1 - Nov 2

A spacious indoor area with a white sofa set, round tables, and large windows offering views of the outdoors.

7. Spark by Hilton Chincoteague Island

Piney Island, 1.6 km from Deep Hole

Ursula

₩138,238 total

includes taxes & fees

Nov 1 - Nov 2

A hot tub in a room with large windows overlooking a water body and grassy area.

8. Waterside Inn

Downtown Chincoteague, 2.9 km from Deep Hole

Genna

₩92,118 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with a bed, a sofa, a desk, and a radiator.

9. Chincoteague Inn

Downtown Chincoteague, 1.2 km from Deep Hole

Amy

₩118,915 total

includes taxes & fees

Oct 11 - Oct 12

A large two-story house with a balcony, a covered patio, and a view of the water.

10. Island Resort

Downtown Chincoteague, 1.7 km from Deep Hole

Robert

₩195,676 total

includes taxes & fees

Oct 17 - Oct 18

A swimming pool with lounge chairs and a view of a sunset over water.

11. Anchor Inn

Downtown Chincoteague, 2.8 km from Deep Hole

rich

₩139,449 total

includes taxes & fees

Nov 1 - Nov 2

A pool area with a building that has a covered patio and a gazebo.

12. Atlantic Shores Inn and Suites

Downtown Chincoteague, 1.3 km from Deep Hole

Dave

₩120,563 total

includes taxes & fees

Oct 17 - Oct 18

A spacious dining area with multiple tables and chairs, a television mounted on an orange wall, and a statue in the center.

13. Days Inn by Wyndham Chincoteague Island

Piney Island, 1.4 km from Deep Hole

Laura

₩111,310 total

includes taxes & fees

Oct 20 - Oct 21

14. Maddox Inn

Downtown Chincoteague, 1.6 km from Deep Hole

Susan

₩116,502 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with lounge chairs and a gazebo.

15. Birchwood Inn

Downtown Chincoteague, 3.2 km from Deep Hole

Aspen

₩142,844 total

includes taxes & fees

Oct 5 - Oct 6

16. Blufin Bungalows & Marina

Down the Marsh, 5.4 km from Deep Hole

Angela

₩308,660 total

includes taxes & fees

Oct 13 - Oct 14

A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

17. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

Up the Neck, 1.5 km from Deep Hole

₩497,537 total

includes taxes & fees

Oct 8 - Oct 9

A modern lobby with a reception desk, seating area, and artwork on the walls.

18. Best Western Plus Pocomoke City

23.6 km from Deep Hole

alexis

₩170,410 total

includes taxes & fees

Nov 1 - Nov 2

A reception area with a wooden cabinet, a green sofa, and a black reception desk.

19. Studio 6 Suites Pocomoke City, MD

21 km from Deep Hole

Brandon

₩112,575 total

includes taxes & fees

Oct 11 - Oct 12

A lobby with a tiled floor, a vending machine, a refrigerator, and a lamp.

20. Motel 6 Pocomoke City, MD

21 km from Deep Hole

Debra

₩105,069 total

includes taxes & fees

Oct 5 - Oct 6

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Where to stay in Deep Hole

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

A group of horses grazing in a lush green field with a river in the foreground.

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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A coastal landscape with a clear blue sky, a calm sea, and a marshy area with water reflecting the sky.

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 Assateague Point.

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Birch Town

While Birch Town isn't home to many top sights, Maui Jack's Waterpark and Museum of Chincoteague are some notable places to visit nearby.

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Top Deep Hole Hotel Reviews

Waterside Inn

10/10 Excellent

"The room and balcony were great, breakfast delicious, and the staff friendly."

Spark by Hilton Chincoteague Island

10/10 Excellent

"This hotel has been thoughtfully updated, and our room was comfortably planned and furnished. The simple breakfast was surprisingly varied, considering the size of the hotel, and the staff were friendly and very supportive. The hotel is close to the entrance to the National Wildlife Refuge, and has the Museum of Chincoteague Island on one side, and the Blackfin restaurant on the other. I’m almost cringing at the thought of others being there when we want to go …. but they deserve all the credit I have given them."

Maddox Inn

8/10 Good

"This is a good located motel. Very nice and genuinely friendly stuff! The rooms are quite outdated, and you can smell it. We stayed there for one night as part of our road trip with our dog, so it served the purpose, but the smell of very old house really bothered me the whole night. As of my knowledge, they are planning some renovation, so it could be gone after that. Otherwise, we liked the area very much!"

Birchwood Inn

8/10 Good

"Stayed here for 4 nights, Checking in through a phone call and Housekeeping checking on us 1 time was the extent of staff interaction. We got a room with a kitchenette and honestly it was very helpful. Small and definitely used but not dirty. There were a few flies but it’s Chincoteague so it’s not surprising. The weather was pretty nasty and the hotels driveway was completely flooded but we had a safe and dry place to stay. The beds were perfect, I love a firm bed. Really the only complaint is I wish they provided kitchen utensils, so I didn’t have to bring them. Looks like they are going to be doing some upgrades or refurbishing the rooms. Definitely gonna come back next year."

Find hotels in Deep Hole, Chincoteague

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Our top choices for Deep Hole hotels

1. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

2. Comfort Suites Chincoteague Island Bayfront Resort

3. Hampton Inn & Suites Chincoteague Waterfront

4. Marina Bay Hotel & Suites, an Ascend Collection Hotel

5. Key West Cottages

6. Refuge Inn

7. Spark by Hilton Chincoteague Island

8. Waterside Inn

9. Chincoteague Inn

10. Island Resort

11. Anchor Inn

12. Atlantic Shores Inn and Suites

13. Days Inn by Wyndham Chincoteague Island

14. Maddox Inn

15. Birchwood Inn

16. Blufin Bungalows & Marina

17. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

18. Best Western Plus Pocomoke City

19. Studio 6 Suites Pocomoke City, MD

20. Motel 6 Pocomoke City, MD

Where to stay in Deep Hole

Downtown Chincoteague

Piney Island

Snotty Ridge

Down the Marsh

Birch Town

Top Deep Hole Hotel Reviews

Waterside Inn

Frequently asked questions