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This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

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Our top choices for Deep Hole hotels

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

1. Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
Downtown Chincoteague, 1.9 km from Deep Hole
9.6 out of 10, Exceptional, (1,001 reviews)
"Awesome place in good location. Would definitely recommend!"
United States
Yvette L.
The price is NT$4,159
NT$4,704 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Suites Chincoteague Island Bayfront Resort
A waterfront hotel with multiple balconies, a dock, and a calm water body.

2. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
3.0 star property
Downtown Chincoteague, 2.5 km from Deep Hole
9.2 out of 10, Wonderful, (635 reviews)
"Great location with wonderful breakfast."
United States
Stephanie Lynn
The price is NT$4,544
NT$5,103 total
includes taxes & fees
Sep 27 - Sep 28
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
A swimming pool with lounge chairs and a beach ball.

3. Refuge Inn

Refuge Inn
3.0 star property
Piney Island, 1.5 km from Deep Hole
9.8 out of 10, Exceptional, (1,003 reviews)
"Everything about our stay was excellent will definitely go back"
United States
Joe
The price is NT$5,811
NT$6,526 total
includes taxes & fees
Sep 27 - Sep 28
Refuge Inn
A spacious indoor area with a white sofa set, round tables, and large windows offering views of the outdoors.

4. Spark by Hilton Chincoteague Island

Spark by Hilton Chincoteague Island
2.5 star property
Piney Island, 1.6 km from Deep Hole
9.6 out of 10, Exceptional, (801 reviews)
"Great people very friendly, we’ve always loved staying here."
United States
Cynthia
The price is NT$3,622
NT$4,067 total
includes taxes & fees
Sep 30 - Oct 1
Spark by Hilton Chincoteague Island
A multi-story hotel with a blue roof, located near a marina with boats docked.

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

Marina Bay Hotel & Suites, an Ascend Collection Hotel
2.5 star property
Downtown Chincoteague, 2.8 km from Deep Hole
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean room, very helpful staff."
United States
James
The price is NT$2,944
NT$3,783 total
includes taxes & fees
Oct 4 - Oct 5
Marina Bay Hotel & Suites, an Ascend Collection Hotel
A hotel room with a bed, a sofa, a desk, and a radiator.

6. Chincoteague Inn

Chincoteague Inn
2.0 star property
Downtown Chincoteague, 1.2 km from Deep Hole
8.6 out of 10, Excellent, (1,002 reviews)
"Great location and value."
United States
Michelle
The price is NT$2,828
NT$3,176 total
includes taxes & fees
Sep 27 - Sep 28
Chincoteague Inn
A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.

7. Hampton Inn & Suites Chincoteague Waterfront

Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
Downtown Chincoteague, 2 km from Deep Hole
9.8 out of 10, Exceptional, (817 reviews)
"Great rooms, pleasant staff and great breakfast buffet"
United States
Karen
The price is NT$4,248
NT$4,770 total
includes taxes & fees
Oct 5 - Oct 6
Hampton Inn & Suites Chincoteague Waterfront
A pool area with a building that has a covered patio and a gazebo.

8. Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites
2.0 star property
Downtown Chincoteague, 1.3 km from Deep Hole
7.6 out of 10, Good, (1,000 reviews)
"Clean beds convenient location nice atmosphere"
United States
Tiara
The price is NT$2,543
NT$2,855 total
includes taxes & fees
Sep 9 - Sep 10
Atlantic Shores Inn and Suites
A waterfront house with a balcony, dock, and a view of the water.

9. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague, 1.9 km from Deep Hole
9.8 out of 10, Exceptional, (624 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is NT$6,916
NT$7,767 total
includes taxes & fees
Sep 7 - Sep 8
Key West Cottages
A spacious dining area with multiple tables and chairs, a television mounted on an orange wall, and a statue in the center.

10. Days Inn by Wyndham Chincoteague Island

Days Inn by Wyndham Chincoteague Island
2.0 star property
Piney Island, 1.4 km from Deep Hole
6.8 out of 10, (1,000 reviews)
"The place was clean, reasonably priced, and the owner was very helpful. The beds were very comfortable and breakfast was great. Would definitely stay again."
United States
Laura
The price is NT$2,674
NT$3,003 total
includes taxes & fees
Sep 20 - Sep 21
Days Inn by Wyndham Chincoteague Island
A large two-story house with a balcony, a covered patio, and a view of the water.

11. Island Resort

Island Resort
2.0 star property
Downtown Chincoteague, 1.7 km from Deep Hole
9.4 out of 10, Exceptional, (473 reviews)
"Clean, great breakfast, locals own the business and know the area."
United States
Robert
The price is NT$4,761
NT$5,347 total
includes taxes & fees
Sep 14 - Sep 15
Island Resort
A hot tub in a room with large windows overlooking a water body and grassy area.

12. Waterside Inn

Waterside Inn
2.0 star property
Downtown Chincoteague, 2.9 km from Deep Hole
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean and quiet, nice breakfast and pool by the bay."
United States
Kurt
The price is NT$2,795
NT$3,139 total
includes taxes & fees
Sep 27 - Sep 28
Waterside Inn
A swimming pool with lounge chairs and a view of a sunset over water.

13. Anchor Inn

Anchor Inn
2.0 star property
Downtown Chincoteague, 2.8 km from Deep Hole
8.8 out of 10, Excellent, (631 reviews)
"Beautiful room and a fun stay!"
United States
rich
The price is NT$3,214
NT$3,609 total
includes taxes & fees
Oct 4 - Oct 5
Anchor Inn

14. Maddox Inn

Maddox Inn
2.0 star property
Downtown Chincoteague, 1.6 km from Deep Hole
7.2 out of 10, Good, (822 reviews)
"This property is centrally located along Maddox Blvd in beautiful Chincoteague. Easily in walking distance are shops and a tremendous ice cream and coffee shop, Mister Whippy. The rooms are clean, just a little outdated, but the staff informed us a refresh is coming. Definitely a nice place to stay for the weekend."
United States
George
The price is NT$3,142
NT$3,529 total
includes taxes & fees
Sep 13 - Sep 14
Maddox Inn
A swimming pool with lounge chairs and a gazebo.

15. Birchwood Inn

Birchwood Inn
2.5 star property
Downtown Chincoteague, 3.2 km from Deep Hole
7.0 out of 10, Good, (447 reviews)
"Very clean Well lit parking Bed comfortable"
United States
Maryann
The price is NT$2,828
NT$3,335 total
includes taxes & fees
Sep 13 - Sep 14
Birchwood Inn
A modern lobby with a reception desk, seating area, and artwork on the walls.

16. Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
2.5 star property
23.6 km from Deep Hole
8.6 out of 10, Excellent, (989 reviews)
"Beautiful clean hotel great breakfast and breakfast staff great staff all together!"
United States
alexis
The price is NT$3,750
NT$4,200 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus Pocomoke City

17. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh, 5.4 km from Deep Hole
9.6 out of 10, Exceptional, (316 reviews)
"Loved sitting on the porch and just seeing water, water everywhere!!"
United States
David
The price is NT$4,560
NT$6,903 total
includes taxes & fees
Sep 7 - Sep 8
Blufin Bungalows & Marina
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.

18. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck, 1.5 km from Deep Hole
The price is NT$3,686
NT$11,342 total
includes taxes & fees
Sep 16 - Sep 17
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A reception area with a wooden cabinet, a green sofa, and a black reception desk.

19. Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD
2.0 star property
21 km from Deep Hole
7.4 out of 10, Good, (82 reviews)
"They were under construction.. room was old.. ceiling falling. But new floors. It was clean enough... but not a nice place. I stayed 1 night but found a different place to stay my 2nd night."
United States
Jeffrey
The price is NT$2,380
NT$2,666 total
includes taxes & fees
Sep 14 - Sep 15
Studio 6 Suites Pocomoke City, MD
A large, two-story house with a porch and a garden with purple flowers.

20. Garden and Sea Inn

Garden and Sea Inn
3.5 star property
16.4 km from Deep Hole
9.4 out of 10, Exceptional, (30 reviews)
"It was very quiet and comfortable! The Innkeeper accommodated personal needs in her preparation and serving of her great breakfasts. Everything was clean and well kept. She gave helpful suggestions for activities and places to eat. Very nice place!"
United States
Florence
The price is NT$6,959
NT$7,675 total
includes taxes & fees
Oct 5 - Oct 6
Garden and Sea Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Where to stay in Deep Hole

Find the best Deep Hole areas and neighborhoods for the activities you enjoy most.
A horse grazing in a lush green field with a small stream.
Photo by Michael Gibson
Open Photo by Michael Gibson

Downtown Chincoteague

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

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.

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.

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.

Birch Town

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

Top Deep Hole Hotel Reviews

Waterside Inn

Waterside Inn

10/10 Excellent
"Convenient location, clean, loved fishing and crabbing right off their pier. Bonus was watching the perfect sunset right off our balcony."
Maria 2-night trip
Posted 21 hours ago
Waterside Inn

Frequently asked questions

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 91 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.

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