Find hotels in Deep Hole, Chincoteague

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Dec 4 - Dec 5
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Dec 5 - Dec 6
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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Discover Deep Hole hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
Hampton Inn & Suites Chincoteague Waterfront

Hampton Inn & Suites Chincoteague Waterfront

2.5 star property
Downtown Chincoteague, 1.2 mi from Deep Hole
9.8 out of 10, Exceptional, (740)
"Exceptional Service- Safe & Relaxingly Quiet - Thank You!"
United States
Jeffery
$87 nightly
The price is $98
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn & Suites Chincoteague Waterfront
Indoor pool, outdoor pool, pool umbrellas, sun loungers
Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 star property
Downtown Chincoteague, 1.2 mi from Deep Hole
9.6 out of 10, Exceptional, (1001)
"The staff were wonderful, and the hospitality was amazing. Enjoyed our stay!"
United States
Regina
$95 nightly
The price is $108
Dec 10 - Dec 11
Total with taxes and fees
Comfort Suites Chincoteague Island Bayfront Resort
Free daily on-the-go breakfast
Days Inn by Wyndham Chincoteague Island

Days Inn by Wyndham Chincoteague Island

2.0 star property
Piney Island, 0.9 mi from Deep Hole
6.8 out of 10, (1000)
"Loved the staff so personable . Location convenient to get around. "
United States
Tina
$63 nightly
The price is $71
Jan 2 - Jan 3, 2026
Total with taxes and fees
Days Inn by Wyndham Chincoteague Island
Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague, 1.2 mi from Deep Hole
9.8 out of 10, Exceptional, (485)
"We love Key West Cottages!"
United States
Jonathan
$94 nightly
The price is $105
Dec 7 - Dec 8
Total with taxes and fees
Key West Cottages
Aerial view
Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

2.5 star property
Downtown Chincoteague, 1.8 mi from Deep Hole
9.0 out of 10, Wonderful, (1000)
"Very clean and courteous staff!"
United States
Nancy
$81 nightly
The price is $90
Dec 25 - Dec 26
Total with taxes and fees
Marina Bay Hotel & Suites, an Ascend Collection Hotel
Seasonal outdoor pool
Waterside Inn

Waterside Inn

2.0 star property
Downtown Chincoteague, 1.8 mi from Deep Hole
9.0 out of 10, Wonderful, (1000)
"great staff, good rates, nice views, good beds, nice pier"
United States
Roy
$65 nightly
The price is $74
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterside Inn
Outdoor pool
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

2.5 star property
Downtown Chincoteague, 1.5 mi from Deep Hole
9.2 out of 10, Wonderful, (576)
"Nice, reasonably priced "
Canada
Bhaskar
$116 nightly
The price is $130
Dec 9 - Dec 10
Total with taxes and fees
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 mi 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
$79 nightly
The price is $89
Dec 11 - Dec 12
Total with taxes and fees
Spark by Hilton Chincoteague Island
Indoor pool, seasonal outdoor pool, sun loungers
Refuge Inn

Refuge Inn

3.0 star property
Piney Island, 0.9 mi from Deep Hole
9.8 out of 10, Exceptional, (1000)
"Great place to stay!"
United States
Robert
$92 nightly
The price is $104
Dec 10 - Dec 11
Total with taxes and fees
Refuge Inn
Indoor pool
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

2.5 star property
14.7 mi from Deep Hole
8.6 out of 10, Excellent, (877)
"Clean and comfortable rooms, wonderful staff"
United States
Brenda
$93 nightly
The price is $103
Jan 1 - Jan 2, 2026
Total with taxes and fees
Best Western Plus Pocomoke City
BBQ/picnic area
Maddox Inn

Maddox Inn

2.0 star property
Downtown Chincoteague, 1 mi from Deep Hole
7.2 out of 10, Good, (777)
"Great staff. Good accommodations for the price. "
United States
Jon
Maddox Inn
Reception
Econo Lodge Pocomoke City Hwy 13

Econo Lodge Pocomoke City Hwy 13

2.0 star property
12.2 mi from Deep Hole
5.6 out of 10, (777)
"Dog friendly environment "
United States
Robyn
$71 nightly
The price is $79
Dec 7 - Dec 8
Total with taxes and fees
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, 0.8 mi from Deep Hole
7.4 out of 10, Good, (1000)
"Good breakfast, good price, kind staff"
United States
Barbara
$79 nightly
The price is $89
Dec 7 - Dec 8
Total with taxes and fees
Atlantic Shores Inn and Suites
Exterior
Island Resort

Island Resort

2.0 star property
Downtown Chincoteague, 1 mi from Deep Hole
9.2 out of 10, Wonderful, (451)
"Beautiful place, very well kept, great breakfast, great location, super clean."
United States
Anna
$130 nightly
The price is $146
Dec 5 - Dec 6
Total with taxes and fees
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
13.1 mi 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
$70 nightly
The price is $78
Dec 6 - Dec 7
Total with taxes and fees
Motel 6 Pocomoke City, MD
Seasonal outdoor pool, open 9:00 AM to 9 PM, sun loungers
Anchor Inn

Anchor Inn

2.0 star property
Downtown Chincoteague, 1.8 mi from Deep Hole
8.8 out of 10, Excellent, (568)
"Great water and sunset views. Helpful, courteous staff."
United States
Howard
$76 nightly
The price is $85
Dec 7 - Dec 8
Total with taxes and fees
Anchor Inn
Property amenity
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2.0 star property
13 mi 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
$70 nightly
The price is $78
Dec 7 - Dec 8
Total with taxes and fees
Studio 6 Suites Pocomoke City, MD
Front of property
Garden and Sea Inn

Garden and Sea Inn

3.5 star property
10.2 mi 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
$209 nightly
The price is $231
Dec 5 - Dec 6
Total with taxes and fees
Garden and Sea Inn
Seasonal outdoor pool
Birchwood Inn

Birchwood Inn

2.5 star property
Downtown Chincoteague, 2 mi from Deep Hole
6.8 out of 10, (388)
"Great staff, great location. Will stay here again "
United States
Zariyah
$64 nightly
The price is $71
Dec 5 - Dec 6
Total with taxes and fees
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.

Piney Island

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

Chincoteague which includes signage, a beach and bird life

Downtown Chincoteague

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

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.

Up the Neck

If you're looking for some top things to see and do in Up the Neck and surrounding area, you can visit Oyster Bay and Captain Timothy Hill House.

Top Deep Hole Hotel Reviews

Waterside Inn

Waterside Inn

10/10 Excellent
"Nice accommodations for the Holiday with a front row seat for the Sunsets."
Sallie 2-night trip
Posted 3 days ago
Waterside Inn

Frequently asked questions

Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Deep Hole hotel for you.
How can I save on a Deep Hole hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Deep Hole hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Deep Hole hotel?
Prices for hotels in Deep Hole often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.