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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

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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

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, (650 reviews)
"Great staff, beautiful view of the bay & a nice hot breakfast buffet"
United States
Dianne
The price is ₩158,776
₩178,305 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.

2. 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, (1,003 reviews)
"Best room on the island"
United States
Jeffrey
The price is ₩143,939
₩163,044 total
includes taxes & fees
Nov 11 - Nov 12
Comfort Suites Chincoteague Island Bayfront Resort
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

Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
Downtown Chincoteague, 2 km from Deep Hole
9.8 out of 10, Exceptional, (828 reviews)
"The hotel was extremely clean and rooms were very comfortable."
United States
David
The price is ₩135,667
₩152,352 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Chincoteague Waterfront
A multi-story hotel with a blue roof, located near a marina with boats docked.

4. 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, (1,003 reviews)
"The front desk staff was efficient, kind and understanding. I had a positive experience with Madison at the front desk. The facility is well maintained and clean."
United States
Michelle
The price is ₩100,936
₩133,367 total
includes taxes & fees
Nov 8 - Nov 9
Marina Bay Hotel & Suites, an Ascend Collection Hotel
A swimming pool with lounge chairs and a beach ball.

5. Refuge Inn

Refuge Inn
3.0 star property
Piney Island, 1.5 km from Deep Hole
9.8 out of 10, Exceptional, (1,001 reviews)
"There are so many things we loved about this place, location, breakfast amenities, the rooms were clean and of course the ponies on the property. We would definitely stay here again."
United States
Karen
The price is ₩181,058
₩203,328 total
includes taxes & fees
Nov 1 - Nov 2
Refuge Inn
A waterfront house with a balcony, dock, and a view of the water.

6. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague, 1.9 km from Deep Hole
9.8 out of 10, Exceptional, (661 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is ₩269,104
₩302,204 total
includes taxes & fees
Oct 19 - Oct 20
Key West Cottages
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

Spark by Hilton Chincoteague Island
2.5 star property
Piney Island, 1.6 km from Deep Hole
9.6 out of 10, Exceptional, (823 reviews)
"Lovely, welcoming hotel."
Canada
Mary
The price is ₩112,277
₩126,087 total
includes taxes & fees
Nov 5 - Nov 6
Spark by Hilton Chincoteague Island
A hot tub in a room with large windows overlooking a water body and grassy area.

8. Waterside Inn

Waterside Inn
2.0 star property
Downtown Chincoteague, 2.9 km from Deep Hole
9.0 out of 10, Wonderful, (1,005 reviews)
"The staff was great and helpful."
United States
Willard
The price is ₩81,656
₩91,700 total
includes taxes & fees
Oct 22 - Oct 23
Waterside Inn
A large two-story house with a balcony, a covered patio, and a view of the water.

9. Island Resort

Island Resort
2.0 star property
Downtown Chincoteague, 1.7 km from Deep Hole
9.2 out of 10, Wonderful, (486 reviews)
"Clean and comfortable rooms, beautiful views. Friendly staff"
United States
Brenda
The price is ₩173,453
₩194,788 total
includes taxes & fees
Oct 19 - Oct 20
Island Resort
A hotel room with a bed, a sofa, a desk, and a radiator.

10. Chincoteague Inn

Chincoteague Inn
2.0 star property
Downtown Chincoteague, 1.2 km from Deep Hole
8.6 out of 10, Excellent, (1,001 reviews)
"Large clean room, easy check in and out, great location and value for money"
United States
Amy
The price is ₩105,406
₩118,375 total
includes taxes & fees
Oct 20 - Oct 21
Chincoteague Inn
A pool area with a building that has a covered patio and a gazebo.

11. 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, (1,003 reviews)
"Everything was great for an overnight stay, a bit off Rte 13, since we were just traveling through, but great staff and fine rustic room"
United States
Dave
The price is ₩106,873
₩120,015 total
includes taxes & fees
Oct 19 - Oct 20
Atlantic Shores Inn and Suites
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

Days Inn by Wyndham Chincoteague Island
2.0 star property
Piney Island, 1.4 km from Deep Hole
6.8 out of 10, (1,002 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 ₩90,729
₩101,888 total
includes taxes & fees
Nov 16 - Nov 17
Days Inn by Wyndham Chincoteague Island
Beach

13. Maddox Inn

Maddox Inn
2.0 star property
Downtown Chincoteague, 1.6 km from Deep Hole
7.4 out of 10, Good, (842 reviews)
"This is an old-style, mom and pop hotel with lots of character, and the rooms are decent. I enjoyed my stay."
United States
Jeffrey
The price is ₩103,271
₩115,973 total
includes taxes & fees
Nov 1 - Nov 2
Maddox Inn
A modern lobby with a reception desk, seating area, and artwork on the walls.

14. 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, (1,002 reviews)
"Bed was comfortable, everything was clean, staff are very helpful and nice."
United States
Rachel
The price is ₩151,464
₩169,636 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Pocomoke City
A large, two-story house with a porch and a garden with purple flowers.

15. 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)
"Grace was an unbelievable host...saw to our needs, can not say enough POSITIVE about this B&B....would love to find an excuse to return. "
United States
Douglas
The price is ₩305,543
₩337,018 total
includes taxes & fees
Oct 21 - Oct 22
Garden and Sea Inn
A reception area with a wooden cabinet, a green sofa, and a black reception desk.

16. Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD
2.0 star property
21 km from Deep Hole
7.6 out of 10, Good, (91 reviews)
"We stayed for one night and it was definitely a great place for it plus we got lost on where our room is and even though it was late the guy was very nice to still be nice and help us out(:"
United States
Brandon
The price is ₩100,055
₩112,063 total
includes taxes & fees
Oct 25 - Oct 26
Studio 6 Suites Pocomoke City, MD
A lobby with a tiled floor, a vending machine, a refrigerator, and a lamp.

17. Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD
2.0 star property
21 km from Deep Hole
5.4 out of 10, (509 reviews)
"All the staff here is amazing. They are friendly and very friendly to help you."
United States
Debra
The price is ₩93,384
₩104,592 total
includes taxes & fees
Oct 22 - Oct 23
Motel 6 Pocomoke City, MD
A spacious lobby with a curved reception desk, a seating area with a sofa, and a patterned carpet.

18. Econo Lodge Pocomoke City Hwy 13

Econo Lodge Pocomoke City Hwy 13
2.0 star property
19.5 km from Deep Hole
5.4 out of 10, (851 reviews)
"Nice staff, helped out when needed"
United States
Deidre
The price is ₩78,054
₩87,420 total
includes taxes & fees
Nov 8 - Nov 9
Econo Lodge Pocomoke City Hwy 13
A brick pathway leading to a pool area with a fence and potted plants.

19. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
26.9 km from Deep Hole
8.4 out of 10, Very good, (7 reviews)
"I fell in love with the charm of this Inn, I can't wait for the restaurant to be up and running so I can come back and stay."
United States
Hans
The price is ₩286,757
₩321,167 total
includes taxes & fees
Oct 19 - Oct 20
Cypress River Inn & Spa
A swimming pool with lounge chairs and a gazebo.

20. Birchwood Inn

Birchwood Inn
2.5 star property
Downtown Chincoteague, 3.2 km from Deep Hole
6.8 out of 10, (460 reviews)
"It was very clean, and nice area"
United States
Aspen
Birchwood 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.
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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.
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 Assateague Point.

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.

Top Deep Hole Hotel Reviews

Chincoteague Inn

Chincoteague Inn

10/10 Excellent
"The place was nice, the staff wasn't very knowledgeable in the are or attractions."
CHRIS 2-night trip
Posted 7 hours ago
Chincoteague 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 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.