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Check prices for these dates

This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

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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, (660 reviews)
"Great staff, beautiful view of the bay & a nice hot breakfast buffet"
United States
Dianne
The price is ₩159,925
₩179,597 total
includes taxes & fees
Dec 7 - Dec 8
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, (1,004 reviews)
"Best room on the island"
United States
Jeffrey
The price is ₩133,316
₩151,125 total
includes taxes & fees
Dec 7 - Dec 8
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, (833 reviews)
"Great view, lovely staff, delicious breakfast !"
United States
Jessica
The price is ₩131,313
₩147,465 total
includes taxes & fees
Dec 10 - Dec 11
Hampton Inn & Suites Chincoteague Waterfront
A modern lobby with a wooden sofa, teal ottomans, and a striped wall.

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, (1,000 reviews)
"Very nice hotel! The decor was really unique and the staff were very helpful! Would definitely recommend!"
United States
Kimberly
The price is ₩97,072
₩129,490 total
includes taxes & fees
Nov 16 - Nov 17
Marina Bay Hotel & Suites, an Ascend Collection Hotel
A round table with a plate of food, two mugs, and two glasses of orange juice on a balcony.

5. Refuge Inn

Refuge Inn
3.0 star property
Piney Island, 1.5 km from Deep Hole
9.8 out of 10, Exceptional, (1,002 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 ₩131,305
₩147,456 total
includes taxes & fees
Dec 9 - Dec 10
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, (674 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is ₩164,776
₩185,043 total
includes taxes & fees
Nov 30 - Dec 1
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, (829 reviews)
"The staff and amenities were excellent at this hotel. The views were also beautiful. Right across the street or all the shops you need for peeing suits, renting bikes, etc."
United States
Patricia
The price is ₩114,889
₩129,021 total
includes taxes & fees
Nov 19 - Nov 20
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, (1,010 reviews)
"Great location , good breakfast, friendly staff. Great for a couples weekend get a way !"
United States
Faith
The price is ₩82,247
₩92,363 total
includes taxes & fees
Dec 7 - Dec 8
Waterside Inn
A balcony with two chairs and a view of a calm body of water with a small island.

9. Island Resort

Island Resort
2.0 star property
Downtown Chincoteague, 1.7 km from Deep Hole
9.2 out of 10, Wonderful, (488 reviews)
"Clean and comfortable rooms, beautiful views. Friendly staff"
United States
Brenda
The price is ₩174,708
₩196,197 total
includes taxes & fees
Dec 5 - Dec 6
Island Resort
A compact kitchenette with a built-in refrigerator, a coffee maker, and a sink with a granite countertop.

10. sea shell motel

sea shell motel
2.0 star property
2.2 km from Deep Hole
10.0 out of 10, Exceptional, (5 reviews)
"Though not overly fancy, the room decor and furnishings were pleasant, and the room was clean and well-maintained. The beds and linen were comfortable. No breakfast was included, but the refrigerator was larger than expected, and the motel is located within walking distance to eateries. The location is quiet yet convenient. Overall, it was a pleasant stay and an excellent off-season value."
United States
Edmund
The price is ₩72,571
₩81,495 total
includes taxes & fees
Dec 10 - Dec 11
sea shell motel
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, (1,001 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 ₩107,647
₩120,885 total
includes taxes & fees
Nov 11 - Nov 12
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, (1,000 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 ₩90,310
₩101,417 total
includes taxes & fees
Nov 11 - Nov 12
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, (845 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 ₩104,018
₩116,812 total
includes taxes & fees
Nov 11 - Nov 12
Maddox Inn
Exterior

14. 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, (344 reviews)
"We had a wonderful stay! The bungalow was nice, clean, and peaceful. It was the perfect place to relax and unwind. Would definitely stay again!"
United States
Rebecca
The price is ₩121,648
₩213,273 total
includes taxes & fees
Dec 1 - Dec 2
Blufin Bungalows & Marina
A modern lobby with a reception desk, seating area, and artwork on the walls.

15. 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, (1,001 reviews)
"Bed was comfortable, everything was clean, staff are very helpful and nice."
United States
Rachel
The price is ₩128,908
₩144,390 total
includes taxes & fees
Dec 10 - Dec 11
Best Western Plus Pocomoke City
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, (96 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 ₩100,780
₩112,875 total
includes taxes & fees
Dec 10 - Dec 11
Studio 6 Suites Pocomoke City, MD
A large, two-story house with a porch and a garden with purple flowers.

17. 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 ₩280,877
₩309,811 total
includes taxes & fees
Dec 9 - Dec 10
Garden and Sea Inn
A lobby with a tiled floor, a vending machine, a refrigerator, and a lamp.

18. 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 ₩94,060
₩105,349 total
includes taxes & fees
Dec 10 - Dec 11
Motel 6 Pocomoke City, MD
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

Econo Lodge Pocomoke City Hwy 13
2.0 star property
19.5 km from Deep Hole
5.6 out of 10, (865 reviews)
"This is a place suitable for people on a tighter budget."
United States
Rong
The price is ₩78,619
₩88,053 total
includes taxes & fees
Dec 10 - Dec 11
Econo Lodge Pocomoke City Hwy 13
A brick pathway leading to a pool area with a fence and potted plants.

20. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
26.9 km from Deep Hole
8.6 out of 10, Excellent, (8 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 ₩293,428
₩328,640 total
includes taxes & fees
Nov 11 - Nov 12
Cypress River Inn & Spa
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

Compare popular hotels in Deep Hole

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.
Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
9.8
Exceptional
833 reviews
View
A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.
Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
9.6
Exceptional
1,004 reviews
View
A round table with a plate of food, two mugs, and two glasses of orange juice on a balcony.
Refuge Inn
3.0 star property
9.8
Exceptional
1,002 reviews
View
A waterfront house with a balcony, dock, and a view of the water.
Key West Cottages
3.0 star property
9.8
Exceptional
674 reviews
View
A waterfront hotel with multiple balconies, a dock, and a calm water body.
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
3.0 star property
9.2
Wonderful
660 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.
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

Blufin Bungalows & Marina

Blufin Bungalows & Marina

8/10 Good
"This was our first time visiting Chincoteague, and decided to stay 4 nights off season (first weekend in November). While this property is very cute with an amazing view, I think the owners could put a little extra into it to make it outstanding. First, there is only one piece of artwork in the entire bungalow. Some more prints throughout would give it a much better vibe, along with some floor lamps. The ceiling lights were very cold and uninviting. The kitchen could use some more basic tools, and having a hair dryer would be great. Some positives: the beds and couch are very comfy. Everything was super clean when we arrived. Parking spot just for us, along with more parking for additional cars. The view, especially at sunset, is INCREDIBLE! I highly recommend happy hour on the porch! A short drive to all attractions was also much appreciated. I would definitely recommend this to another couple or small family."
Anonymous traveler 4-night trip
Posted 2 hours ago
Blufin Bungalows & Marina

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.