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Check prices for these dates

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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Our top choices for Deep Hole hotels

Terrace/patio

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, (778 reviews)
"This hotel is close to the entrance to Assateague National Seashore. Check in was quick, room was spacious and clean. Breakfast selection was sufficient was bagels, assorted cereal, oatmeal, yogurt and fresh fruits. "
United States
Veronica
The price is ₩209,367
₩235,120 total
includes taxes & fees
Jun 1 - Jun 2
Spark by Hilton Chincoteague Island
Indoor spa tub

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)
"Very quaint and quiet place to stay in the off season. Staff very friendly. Great view from the room. Would stay again."
United States
Amy
The price is ₩166,386
₩186,851 total
includes taxes & fees
Jun 1 - Jun 2
Waterside Inn
Indoor pool, seasonal outdoor pool, sun loungers

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)
"Great location and experience. "
United States
Heather
The price is ₩258,019
₩289,756 total
includes taxes & fees
Jun 4 - Jun 5
Refuge Inn
Seasonal outdoor pool

Birchwood Inn

Birchwood Inn
2.5 star property
Downtown Chincoteague, 3.2 km from Deep Hole
7.0 out of 10, Good, (394 reviews)
"Needs severe updates"
United States
lisa
The price is ₩102,122
₩122,224 total
includes taxes & fees
May 31 - Jun 1
Birchwood Inn
Outdoor pool

Chincoteague Inn

Chincoteague Inn
2.0 star property
Downtown Chincoteague, 1.2 km from Deep Hole
8.4 out of 10, Very Good, (1,000 reviews)
"Been staying there the last few times and it’s convenient and affordable. I will he continuing to stay there. Be sure to tip the cleaners. They do a great job!!"
United States
Hemillo
The price is ₩118,498
₩133,078 total
includes taxes & fees
May 31 - Jun 1
Chincoteague Inn
Lobby

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)
"This is absolutely out favorite hotel to stay at the staff is so friendly and the rooms are super clean an they even have a nice free lil breakfast. Housekeeper ladies are so nice as well . We love this place ."
United States
Ashley
The price is ₩132,598
₩148,906 total
includes taxes & fees
Jun 3 - Jun 4
Days Inn by Wyndham Chincoteague Island
Exterior

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, (258 reviews)
"Loved everything about our stay"
United States
Elizabeth
The price is ₩400,794
₩534,316 total
includes taxes & fees
Jun 4 - Jun 5
Blufin Bungalows & Marina
Restaurant

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, (931 reviews)
"Great breakfast, clean rooms "
United States
Caitlin
The price is ₩193,497
₩216,717 total
includes taxes & fees
May 31 - Jun 1
Best Western Plus Pocomoke City
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, (1,000 reviews)
"Friendly Staff, very clean nice breakfast Will be my go to place when I’m in town for business"
United States
lisa
The price is ₩133,648
₩150,088 total
includes taxes & fees
Jun 1 - Jun 2
Atlantic Shores Inn and Suites
Palm Cottage | 1 bedroom, premium bedding, individually decorated

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague, 1.9 km from Deep Hole
9.8 out of 10, Exceptional, (567 reviews)
"Great place to stay on the island"
United States
Wilmer
The price is ₩326,830
₩367,030 total
includes taxes & fees
Jun 1 - Jun 2
Key West Cottages
Lobby

Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD
2.0 star property
21 km from Deep Hole
7.8 out of 10, Good, (64 reviews)
"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 ₩119,983
₩134,383 total
includes taxes & fees
May 29 - May 30
Studio 6 Suites Pocomoke City, MD
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, (1,000 reviews)
"Check staff was nice clean room comfortable beds very nice area walkable to Main Street"
United States
Jon
The price is ₩226,572
₩276,942 total
includes taxes & fees
May 31 - Jun 1
Marina Bay Hotel & Suites, an Ascend Collection Hotel
Seasonal outdoor pool, open 9:00 AM to 9 PM, pool umbrellas

Anchor Inn

Anchor Inn
2.0 star property
Downtown Chincoteague, 2.8 km from Deep Hole
8.8 out of 10, Excellent, (588 reviews)
"Pretty great place "
United States
Nicholas
The price is ₩189,972
₩213,342 total
includes taxes & fees
Jun 1 - Jun 2
Anchor Inn
Exterior

Island Resort

Island Resort
2.0 star property
Downtown Chincoteague, 1.7 km from Deep Hole
9.2 out of 10, Wonderful, (453 reviews)
"Perfect spot to enjoy the Island and all its glory. Kids enjoyed the indoor pool and the view was perfect from the balcony. Clean and accommodating. My second stay here and would plan on it again. "
United States
Maria
The price is ₩224,997
₩252,672 total
includes taxes & fees
May 29 - May 30
Island Resort
Beach nearby

Maddox Inn

Maddox Inn
2.0 star property
Downtown Chincoteague, 1.6 km from Deep Hole
7.2 out of 10, Good, (784 reviews)
"Great pet friendly place."
United States
stewart
The price is ₩184,498
₩207,193 total
includes taxes & fees
May 30 - May 31
Maddox Inn
Exterior

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)
"Very nice place to stay. "
United States
Lisa
The price is ₩282,866
₩319,235 total
includes taxes & fees
May 31 - Jun 1
Comfort Suites Chincoteague Island Bayfront Resort
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, (782 reviews)
"Everything was great!!"
United States
Debbie
The price is ₩278,996
₩313,313 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn & Suites Chincoteague Waterfront
View from property

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, (602 reviews)
"Our stay was great! "
United States
Troy
The price is ₩268,496
₩301,521 total
includes taxes & fees
Jun 2 - Jun 3
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
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 reviews)
"We loved our stay at the Garden and Sea Inn. Location was perfect to surrounding activities. Inn was charming and comfortable, and the breakfasts were fabulous. Thank you for allowing us to be your guests."
United States
Angela
The price is ₩343,495
₩378,880 total
includes taxes & fees
Jun 3 - Jun 4
Garden and Sea Inn
Reception

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, (792 reviews)
"Clean room. Pleasant staff. "
United States
Richard
The price is ₩122,998
₩137,758 total
includes taxes & fees
May 31 - Jun 1
Econo Lodge Pocomoke City Hwy 13
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.
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.

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 Museum of Chincoteague are some notable places to visit nearby.

Top Deep Hole Hotel Reviews

Hampton Inn & Suites Chincoteague Waterfront

Hampton Inn & Suites Chincoteague Waterfront

10/10 Excellent
"Loved the size of the room for me and the two kids. The balcony was great. We made good use of the pool and fitness room too. The breakfast accommodated us vegetarians by making us special omelets. We enjoyed our stay!"
Todd H 2-night trip
Posted 6 hours ago
Hampton Inn & Suites Chincoteague Waterfront

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 85 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.