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Check prices for these dates

This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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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, (644 reviews)
"Great location with wonderful breakfast."
United States
Stephanie Lynn
The price is ₩161,543
₩181,414 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, (1,000 reviews)
"Great place!"
United States
Marc
The price is ₩161,665
₩182,974 total
includes taxes & fees
Oct 25 - Oct 26
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, (822 reviews)
"Great rooms, pleasant staff and great breakfast buffet"
United States
Karen
The price is ₩139,144
₩156,257 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, (1,000 reviews)
"Clean room, very helpful staff."
United States
James
The price is ₩114,234
₩148,647 total
includes taxes & fees
Oct 25 - Oct 26
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, (1,005 reviews)
"Everything about our stay was excellent will definitely go back"
United States
Joe
The price is ₩184,212
₩206,871 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, (649 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is ₩262,119
₩294,360 total
includes taxes & fees
Oct 15 - Oct 16
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, (815 reviews)
"Just a super nice place to stay and wonderful staff!!!"
United States
Ursula
The price is ₩114,358
₩128,422 total
includes taxes & fees
Oct 12 - Oct 13
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, (1,000 reviews)
"Staff was nice and the breakfast was a good deal. The view was worth the stay"
United States
Genna
The price is ₩83,079
₩93,297 total
includes taxes & fees
Oct 18 - Oct 19
Waterside Inn
A hotel room with a bed, a sofa, a desk, and a radiator.

9. 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)
"Great price, staff, location. Always enjoy my stay here. Pool very well maintained. Staff helpful and friendly."
United States
Sandra
The price is ₩106,965
₩120,126 total
includes taxes & fees
Oct 4 - Oct 5
Chincoteague Inn
A swimming pool with lounge chairs and a view of a sunset over water.

10. Anchor Inn

Anchor Inn
2.0 star property
Downtown Chincoteague, 2.8 km from Deep Hole
8.8 out of 10, Excellent, (640 reviews)
"Beautiful room and a fun stay!"
United States
rich
The price is ₩125,772
₩141,234 total
includes taxes & fees
Nov 1 - Nov 2
Anchor Inn
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
9.2 out of 10, Wonderful, (481 reviews)
"Clean, great breakfast, locals own the business and know the area."
United States
Robert
The price is ₩176,019
₩197,669 total
includes taxes & fees
Oct 19 - Oct 20
Island Resort
A pool area with a building that has a covered patio and a gazebo.

12. 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)
"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 ₩108,454
₩121,793 total
includes taxes & fees
Oct 2 - Oct 3
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.

13. 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 ₩100,128
₩112,444 total
includes taxes & fees
Oct 19 - Oct 20
Days Inn by Wyndham Chincoteague Island
Beach

14. Maddox Inn

Maddox Inn
2.0 star property
Downtown Chincoteague, 1.6 km from Deep Hole
7.2 out of 10, Good, (833 reviews)
"Pet friendly!"
United States
Susan
The price is ₩105,070
₩117,994 total
includes taxes & fees
Nov 1 - Nov 2
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
6.8 out of 10, (458 reviews)
"It was very clean, and nice area"
United States
Aspen
The price is ₩120,641
₩142,250 total
includes taxes & fees
Oct 5 - Oct 6
Birchwood Inn
Exterior

16. 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, (332 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is ₩206,009
₩307,376 total
includes taxes & fees
Oct 13 - Oct 14
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.

17. 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 ₩169,249
₩496,996 total
includes taxes & fees
Oct 8 - Oct 9
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A modern lobby with a reception desk, seating area, and artwork on the walls.

18. 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, (1,004 reviews)
"Beautiful clean hotel great breakfast and breakfast staff great staff all together!"
United States
alexis
The price is ₩154,103
₩172,592 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Pocomoke City
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, (85 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 ₩101,536
₩113,722 total
includes taxes & fees
Oct 8 - Oct 9
Studio 6 Suites Pocomoke City, MD
A lobby with a tiled floor, a vending machine, a refrigerator, and a lamp.

20. Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD
2.0 star property
21 km from Deep Hole
5.4 out of 10, (508 reviews)
"All the staff here is amazing. They are friendly and very friendly to help you."
United States
Debra
The price is ₩94,766
₩106,140 total
includes taxes & fees
Oct 12 - Oct 13
Motel 6 Pocomoke City, MD
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 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

Key West Cottages

Key West Cottages

10/10 Excellent
"Another fabulous stay at Key West Cottages! Great service, spacious cottages, great location, clean and super cute! What more can you ask for!"
Erin 2-night trip
Posted 14 hours ago
Key West Cottages

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.