When is the best time to go to Deep Hole?

When planning your trip to Deep Hole, Virginia, the best time to visit is during the shoulder seasons of spring (April to May) and fall (September to October). These months offer pleasant temperatures, generally ranging from the mid-60s to high 70s Fahrenheit, which are ideal for outdoor activities like hiking, fishing, and exploring the natural surroundings without the intense heat and humidity of summer. You'll also find the natural beauty of the area enhanced by blooming wildflowers in spring or the vibrant fall foliage. Couples looking for a tranquil getaway will particularly appreciate these times. The quieter atmosphere allows for more intimate experiences, whether it's a peaceful walk along the trails or enjoying a meal at one of the local establishments without the larger crowds of peak summer.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Deep Hole.

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.

Top Deep Hole Hotels (Chincoteague)

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Our top choices for Deep Hole hotels

A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.

1. Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague, 1.2 mi from Deep Hole

Marc

$119 nightly

Oct 25 - Oct 26

Total with taxes and fees

A spacious indoor area with a white sofa set, round tables, and large windows offering views of the outdoors.

2. Spark by Hilton Chincoteague Island

Piney Island, 1 mi from Deep Hole

Ursula

$96 nightly

Oct 12 - Oct 13

Total with taxes and fees

A swimming pool with lounge chairs and a beach ball.

3. Refuge Inn

Piney Island, 1 mi from Deep Hole

Joe

$121 nightly

Oct 13 - Oct 14

Total with taxes and fees

A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.

4. Hampton Inn & Suites Chincoteague Waterfront

Downtown Chincoteague, 1.3 mi from Deep Hole

Karen

$110 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hotel room with a bed, a sofa, a desk, and a radiator.

5. Chincoteague Inn

Downtown Chincoteague, 0.8 mi from Deep Hole

Sandra

$79 nightly

Oct 1 - Oct 2

Total with taxes and fees

A multi-story hotel with a blue roof, located near a marina with boats docked.

6. Marina Bay Hotel & Suites, an Ascend Collection Hotel

Downtown Chincoteague, 1.8 mi from Deep Hole

James

$98 nightly

Oct 25 - Oct 26

Total with taxes and fees

A waterfront hotel with multiple balconies, a dock, and a calm water body.

7. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Downtown Chincoteague, 1.5 mi from Deep Hole

Stephanie Lynn

$119 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hot tub in a room with large windows overlooking a water body and grassy area.

8. Waterside Inn

Downtown Chincoteague, 1.8 mi from Deep Hole

Genna

$56 nightly

Oct 18 - Oct 19

Total with taxes and fees

A large two-story house with a balcony, a covered patio, and a view of the water.

9. Island Resort

Downtown Chincoteague, 1 mi from Deep Hole

Robert

$130 nightly

Oct 16 - Oct 17

Total with taxes and fees

A pool area with a building that has a covered patio and a gazebo.

10. Atlantic Shores Inn and Suites

Downtown Chincoteague, 0.8 mi from Deep Hole

Dave

$83 nightly

Oct 6 - Oct 7

Total with taxes and fees

11. Maddox Inn

Downtown Chincoteague, 1 mi from Deep Hole

Dania

$110 nightly

Sep 29 - Sep 30

Total with taxes and fees

A swimming pool with lounge chairs and a view of a sunset over water.

12. Anchor Inn

Downtown Chincoteague, 1.8 mi from Deep Hole

rich

$101 nightly

Oct 4 - Oct 5

Total with taxes and fees

A waterfront house with a balcony, dock, and a view of the water.

13. Key West Cottages

Downtown Chincoteague, 1.2 mi from Deep Hole

Debra

$224 nightly

Oct 18 - Oct 19

Total with taxes and fees

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.

14. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

Up the Neck, 0.9 mi from Deep Hole

$304 nightly

Sep 30 - Oct 1

Total with taxes and fees

A swimming pool with lounge chairs and a gazebo.

15. Birchwood Inn

Downtown Chincoteague, 2 mi from Deep Hole

Aspen

$94 nightly

Sep 29 - Sep 30

Total with taxes and fees

16. Blufin Bungalows & Marina

Down the Marsh, 3.4 mi from Deep Hole

Angela

$202 nightly

Oct 13 - Oct 14

Total with taxes and fees

A reception area with a wooden cabinet, a green sofa, and a black reception desk.

17. Studio 6 Suites Pocomoke City, MD

13 mi from Deep Hole

Christina

$75 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern lobby with a reception desk, seating area, and artwork on the walls.

18. Best Western Plus Pocomoke City

14.7 mi from Deep Hole

alexis

$127 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

12.1 mi from Deep Hole

Deidre

$59 nightly

Oct 19 - Oct 20

Total with taxes and fees

A brick pathway leading to a pool area with a fence and potted plants.

20. Cypress River Inn & Spa

16.7 mi from Deep Hole

Hans

$203 nightly

Sep 29 - Sep 30

Total with taxes and fees

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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.

Downtown Chincoteague

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

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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.

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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.

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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.

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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.

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Top Deep Hole Hotel Reviews

Chincoteague Inn

10/10 Excellent

"Perfect place to stay for a girls weekend!"

Marina Bay Hotel & Suites, an Ascend Collection Hotel

8/10 Good

"Was told I received a complimentary upgrade at check-in when I originally booked a room with a King and our so called “complimentary upgrade” was a room with two queens. I would’ve complained had we not stayed in places with separate beds before. There was a wedding party there and when they returned after the wedding in the evening, they were quite drunk and disorderly yelling through the halls. The walls were very thin. Could hear our neighbors consistently. Was disappointed that the floors were sticky and the shampoo, body wash holders were empty. Cleaning was very lackluster. Nice hotel overall though."

Cozy 2-bedroom house in Chincoteague

10/10 Excellent

"The cottage is adorable and the owners are superb! The house was super clean, well-appointed, and in a very quiet area. I would gladly stay her again.pros:quiet well stocked kitchenwasher/dryernice tub/showercomfy bedsgreat ownerslot of thick towels and pillowscons:mosquitoes! (nothing the owner could do about this as it is the entire area)good to know:steps to front entrancetall sides to tub might be an issue for somewear bug spray everywhere!Assateague beach is close and easy to accesseverything on Chincoteague Island is easily accessible"

Find hotels in Deep Hole, Chincoteague

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Deep Hole hotels

1. Comfort Suites Chincoteague Island Bayfront Resort

2. Spark by Hilton Chincoteague Island

3. Refuge Inn

4. Hampton Inn & Suites Chincoteague Waterfront

5. Chincoteague Inn

6. Marina Bay Hotel & Suites, an Ascend Collection Hotel

7. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

8. Waterside Inn

9. Island Resort

10. Atlantic Shores Inn and Suites

11. Maddox Inn

12. Anchor Inn

13. Key West Cottages

14. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

15. Birchwood Inn

16. Blufin Bungalows & Marina

17. Studio 6 Suites Pocomoke City, MD

18. Best Western Plus Pocomoke City

19. Econo Lodge Pocomoke City Hwy 13

20. Cypress River Inn & Spa

Where to stay in Deep Hole

Downtown Chincoteague

Piney Island

Snotty Ridge

Down the Marsh

Birch Town

Top Deep Hole Hotel Reviews

Chincoteague Inn

Frequently asked questions

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