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

Dianne

NT$4,357 total

includes taxes & fees

Oct 29 - Oct 30

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

Diego

NT$3,812 total

includes taxes & fees

Nov 24 - Nov 25

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

Jessica

NT$3,723 total

includes taxes & fees

Nov 10 - Nov 11

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

Joset

NT$3,422 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with lounge chairs and a beach ball.

5. Refuge Inn

Piney Island, 1.5 km from Deep Hole

Karen

NT$4,968 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.

6. Spark by Hilton Chincoteague Island

Piney Island, 1.6 km from Deep Hole

Mary

NT$3,081 total

includes taxes & fees

Nov 5 - Nov 6

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

7. Key West Cottages

Downtown Chincoteague, 1.9 km from Deep Hole

Melissa

NT$7,384 total

includes taxes & fees

Oct 26 - Oct 27

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

Reina

NT$2,241 total

includes taxes & fees

Oct 29 - Oct 30

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

NT$2,892 total

includes taxes & fees

Oct 26 - Oct 27

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

Brenda

NT$4,759 total

includes taxes & fees

Oct 26 - Oct 27

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

11. Atlantic Shores Inn and Suites

Downtown Chincoteague, 1.3 km from Deep Hole

Dave

NT$2,932 total

includes taxes & fees

Oct 26 - Oct 27

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

12. Days Inn by Wyndham Chincoteague Island

Piney Island, 1.4 km from Deep Hole

Laura

NT$2,614 total

includes taxes & fees

Oct 30 - Oct 31

13. Maddox Inn

Downtown Chincoteague, 1.6 km from Deep Hole

Jeffrey

NT$2,834 total

includes taxes & fees

Nov 1 - Nov 2

A motel sign with the name 'Sea Shell Motel' and a seashell graphic.

14. sea shell motel

2.2 km from Deep Hole

NT$1,977 total

includes taxes & fees

Oct 26 - Oct 27

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

15. Best Western Plus Pocomoke City

23.6 km from Deep Hole

Rachel

NT$3,823 total

includes taxes & fees

Nov 22 - Nov 23

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

16. Studio 6 Suites Pocomoke City, MD

21 km from Deep Hole

Brandon

NT$2,738 total

includes taxes & fees

Nov 1 - Nov 2

A large, two-story house with a porch and a garden with purple flowers.

17. Garden and Sea Inn

16.4 km from Deep Hole

Douglas

NT$7,156 total

includes taxes & fees

Oct 26 - Oct 27

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

18. Motel 6 Pocomoke City, MD

21 km from Deep Hole

Debra

NT$2,556 total

includes taxes & fees

Oct 29 - Oct 30

A spacious lobby with a curved reception desk, a seating area with a sofa, and a patterned carpet.

19. Econo Lodge Pocomoke City Hwy 13

19.5 km from Deep Hole

Rong

NT$2,136 total

includes taxes & fees

Nov 15 - Nov 16

A brick pathway leading to a pool area with a fence and potted plants.

20. Cypress River Inn & Spa

26.9 km from Deep Hole

Hans

NT$7,847 total

includes taxes & fees

Oct 26 - Oct 27

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Compare popular hotels in Deep Hole

Property	Property class	Guest rating
Comfort Suites Chincoteague Island Bayfront Resort	2.5 star property	9.6 Exceptional 1,004 reviews	View
Hampton Inn & Suites Chincoteague Waterfront	2.5 star property	9.8 Exceptional 829 reviews	View
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront	3.0 star property	9.2 Wonderful 652 reviews	View
Key West Cottages	3.0 star property	9.8 Exceptional 665 reviews	View
Refuge Inn	3.0 star property	9.8 Exceptional 1,001 reviews	View

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

Key West Cottages

10/10 Excellent

"Property was in pristine condition when we arrived. Cottage was easily accessible from the parking lot and the luggage wagons are a life saver ! Would definitely recommend this place. Staff is so helpful and super kind. We will definitely be back."

Anchor Inn

10/10 Excellent

"I had a wonderful stay at the Anchor Inn in mid-October. I happily used the microwave and mini fridge. My room was the furthest one up closest the docks and water and it was lovely to have my private patio to relax even when the weather wasn't cooperating. The bed was comfy. The room was clean. And even with the winds howling and it being chilly outside, my room felt secure and comfortable. The hotel is very close to the downtown area. You can walk or rent a bike. It is also very close to Assateague Island National Seashore. I went there twice during my stay and had some excellent hikes and saw amazing wildlife. So remember to bring your National Park pass if you have one! The staff at the front desk were very helpful with any questions I had. I had one small issue upon arrival and that was there were some ants crawling around on bathroom sink. That didn't freak me out because the season has been winding down and I'm sure that happens. The staff responded quickly and took care of the issue. One other thing and maybe it was just me, is I wanted to just cast to the TV to watch some stuff I normally watch and I couldn't see a way to do it. I didn't ask. But it was fine. I didn't really have a need to watch much anyway. I highly recommend booking here. It was a delightful stay."

Find hotels in Deep Hole, Chincoteague

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Be picky

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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. Refuge Inn

6. Spark by Hilton Chincoteague Island

7. Key West Cottages

8. Waterside Inn

9. Chincoteague Inn

10. Island Resort

11. Atlantic Shores Inn and Suites

12. Days Inn by Wyndham Chincoteague Island

13. Maddox Inn

14. sea shell motel

15. Best Western Plus Pocomoke City

16. Studio 6 Suites Pocomoke City, MD

17. Garden and Sea Inn

18. Motel 6 Pocomoke City, MD

19. Econo Lodge Pocomoke City Hwy 13

20. Cypress River Inn & Spa

Compare popular hotels in Deep Hole

Where to stay in Deep Hole

Downtown Chincoteague

Piney Island

Snotty Ridge

Down the Marsh

Birch Town

Top Deep Hole Hotel Reviews

Key West Cottages

Frequently asked questions

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