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Top Trending Hotels Near Deep Hole, Chincoteague

Exterior
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, (740)
"Exceptional Service- Safe & Relaxingly Quiet - Thank You!"
United States
Jeffery
The price is ฿2,800
฿3,144 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Chincoteague Waterfront
Indoor pool, outdoor pool, pool umbrellas, pool loungers
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, (1008)
"The staff were wonderful, and the hospitality was amazing. Enjoyed our stay!"
United States
Regina
The price is ฿2,993
฿3,394 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Suites Chincoteague Island Bayfront Resort
Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague, 1.9 km from Deep Hole
9.8 out of 10, Exceptional, (483)
"Great place to stay!"
United States
Paul
The price is ฿3,014
฿3,385 total
includes taxes & fees
2 Dec - 3 Dec
Key West Cottages
Free daily on-the-go breakfast
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, (1001)
"Loved the staff so personable . Location convenient to get around. "
United States
Tina
The price is ฿2,129
฿2,391 total
includes taxes & fees
3 Dec - 4 Dec
Days Inn by Wyndham Chincoteague Island
Seasonal outdoor pool
Waterside Inn

Waterside Inn

2.0 star property
Downtown Chincoteague, 2.9 km from Deep Hole
9.0 out of 10, Wonderful, (1002)
"great staff, good rates, nice views, good beds, nice pier"
United States
Roy
Waterside Inn
Aerial view
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, (1001)
"Very clean and courteous staff!"
United States
Nancy
The price is ฿2,156
฿2,903 total
includes taxes & fees
21 Dec - 22 Dec
Marina Bay Hotel & Suites, an Ascend Collection Hotel
Outdoor pool
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

2.5 star property
Downtown Chincoteague, 2.5 km from Deep Hole
9.2 out of 10, Wonderful, (576)
"I had an enjoyable stay. I will return there the next time I vacation on Chincoteague."
United States
Becca
The price is ฿3,521
฿3,954 total
includes taxes & fees
5 Dec - 6 Dec
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
Property amenity
Spark by Hilton Chincoteague Island

Spark by Hilton Chincoteague Island

2.5 star property
Piney Island, 1.6 km from Deep Hole
9.4 out of 10, Exceptional, (746)
"Staff was very helpful and friendly, our room was exceptional, we enjoyed our stay!"
United States
Danny
The price is ฿2,543
฿2,856 total
includes taxes & fees
7 Dec - 8 Dec
Spark by Hilton Chincoteague Island
Indoor pool
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, (876)
"Clean and comfortable rooms, wonderful staff"
United States
Brenda
The price is ฿2,975
฿3,302 total
includes taxes & fees
1 Jan - 2 Jan 2026
Best Western Plus Pocomoke City
BBQ/picnic Area
Maddox Inn

Maddox Inn

2.0 star property
Downtown Chincoteague, 1.6 km from Deep Hole
7.2 out of 10, Good, (776)
"Great staff. Good accommodations for the price. "
United States
Jon
The price is ฿2,761
฿3,101 total
includes taxes & fees
2 Dec - 3 Dec
Maddox Inn
Reception
Econo Lodge Pocomoke City Hwy 13

Econo Lodge Pocomoke City Hwy 13

2.0 star property
19.6 km from Deep Hole
5.6 out of 10, (777)
"Dog friendly environment "
United States
Robyn
The price is ฿1,686
฿1,871 total
includes taxes & fees
2 Dec - 3 Dec
Econo Lodge Pocomoke City Hwy 13
Seasonal outdoor pool
Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites

2.0 star property
Downtown Chincoteague, 1.3 km from Deep Hole
7.4 out of 10, Good, (1000)
"Good breakfast, good price, kind staff"
United States
Barbara
The price is ฿2,283
฿2,564 total
includes taxes & fees
2 Dec - 3 Dec
Atlantic Shores Inn and Suites
Indoor pool, seasonal outdoor pool, pool loungers
Refuge Inn

Refuge Inn

3.0 star property
Piney Island, 1.5 km from Deep Hole
9.8 out of 10, Exceptional, (1002)
"Great place to stay!"
United States
Robert
The price is ฿3,137
฿3,523 total
includes taxes & fees
7 Dec - 8 Dec
Refuge Inn
Exterior
Island Resort

Island Resort

2.0 star property
Downtown Chincoteague, 1.7 km from Deep Hole
9.2 out of 10, Wonderful, (451)
"Beautiful place, very well kept, great breakfast, great location, super clean."
United States
Anna
The price is ฿4,174
฿4,688 total
includes taxes & fees
2 Dec - 3 Dec
Island Resort
Iron/ironing board, free WiFi, bed sheets, alarm clocks
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2.0 star property
21.1 km from Deep Hole
5.2 out of 10, (492)
"A great Motel 6. We had a comfortable stay and would stay here again if traveling through the area again. You cant go wrong here. "
United States
Michael
The price is ฿2,250
฿2,497 total
includes taxes & fees
2 Dec - 3 Dec
Motel 6 Pocomoke City, MD
Seasonal outdoor pool, open 9:00 AM to 9 PM, pool loungers
Anchor Inn

Anchor Inn

2.0 star property
Downtown Chincoteague, 2.8 km from Deep Hole
8.8 out of 10, Excellent, (568)
"Great water and sunset views. Helpful, courteous staff."
United States
Howard
The price is ฿2,429
฿2,728 total
includes taxes & fees
3 Dec - 4 Dec
Anchor Inn
Property amenity
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, (56)
"Parking was right next to my room, especially important after a long day on the road. Perfect for a quick stop. "
United States
Jennifer
The price is ฿2,250
฿2,497 total
includes taxes & fees
2 Dec - 3 Dec
Studio 6 Suites Pocomoke City, MD
Front of property
Garden and Sea Inn

Garden and Sea Inn

3.5 star property
16.4 km from Deep Hole
9.4 out of 10, Exceptional, (29)
"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 ฿5,748
฿6,340 total
includes taxes & fees
2 Dec - 3 Dec
Garden and Sea Inn
Seasonal outdoor pool
Birchwood Inn

Birchwood Inn

2.5 star property
Downtown Chincoteague, 3.2 km from Deep Hole
6.8 out of 10, (388)
"Great staff, great location. Will stay here again "
United States
Zariyah
The price is ฿1,878
฿2,270 total
includes taxes & fees
2 Dec - 3 Dec
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.
View all properties

Where to stay in Deep Hole

Find the best Deep Hole areas for the activities you enjoy most.

Piney Island

While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.

Chincoteague showing bird life, a sandy beach and signage

Downtown Chincoteague

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

Down the Marsh

While there might not be top attractions in Down the Marsh, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.

Up the Neck

While Up the Neck isn't home to many top sights, Oyster Bay and Captain Timothy Hill House are some notable places to visit nearby.

Snotty Ridge

Snotty Ridge might not have many top sights, but Robert N. Reed Downtown Waterfront Park and Assateague Point are two attractions nearby that you can check out.

Top Deep Hole Hotel Reviews

Blufin Bungalows & Marina

Blufin Bungalows & Marina

10/10 Excellent
"Beautiful cottage. Right on the water. The cooktop and microwave were enough to fit our needs. The screened in porch was a bonus to sit on and watch the sun go down. "
Mary 4-night trip
Posted 6 days ago
Blufin Bungalows & Marina

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Frequently asked questions

What is Deep Hole like?
Travellers to the Deep Hole neighbourhood 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 can I expect to find in the Deep Hole area?
Expedia has 81 hotels and other accommodation options 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, the majority of hotel bookings are refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If your reservation is non-refundable, you might be able to cancel it and be given a refund within a 24-hour period of booking. Enter dates in and click on "Search", then filter by "fully refundable" to get the top deals on offer in Deep Hole.
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.