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)

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Deep Hole hotels

1. Comfort Suites Chincoteague Island Bayfront Resort

Downtown Chincoteague, 1.2 mi from Deep Hole

Marc

$131 nightly

Oct 12 - Oct 13

Total with taxes and fees

2. Atlantic Shores Inn and Suites

Downtown Chincoteague, 0.8 mi from Deep Hole

Sara

$87 nightly

Oct 17 - Oct 18

Total with taxes and fees

3. Spark by Hilton Chincoteague Island

Piney Island, 1 mi from Deep Hole

Ursula

$107 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

Downtown Chincoteague, 1.8 mi from Deep Hole

James

$106 nightly

Oct 4 - Oct 5

Total with taxes and fees

Standard Room, 1 King Bed with Sofa bed, Non Smoking | WiFi (free), alarm clocks, bed sheets

5. Chincoteague Inn

Downtown Chincoteague, 0.8 mi from Deep Hole

Michelle

$89 nightly

Sep 27 - Sep 28

Total with taxes and fees

Indoor pool, seasonal outdoor pool, sun loungers

6. Refuge Inn

Piney Island, 1 mi from Deep Hole

Joe

$134 nightly

Oct 13 - Oct 14

Total with taxes and fees

7. Waterside Inn

Downtown Chincoteague, 1.8 mi from Deep Hole

Genna

$77 nightly

Oct 11 - Oct 12

Total with taxes and fees

8. Island Resort

Downtown Chincoteague, 1 mi from Deep Hole

Robert

$130 nightly

Oct 16 - Oct 17

Total with taxes and fees

9. Hampton Inn & Suites Chincoteague Waterfront

Downtown Chincoteague, 1.3 mi from Deep Hole

Karen

$131 nightly

Oct 7 - Oct 8

Total with taxes and fees

10. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Downtown Chincoteague, 1.5 mi from Deep Hole

Stephanie Lynn

$143 nightly

Sep 27 - Sep 28

Total with taxes and fees

11. Days Inn by Wyndham Chincoteague Island

Piney Island, 0.9 mi from Deep Hole

Laura

$81 nightly

Sep 27 - Sep 28

Total with taxes and fees

12. Maddox Inn

Downtown Chincoteague, 1 mi from Deep Hole

Dania

$110 nightly

Sep 17 - Sep 18

Total with taxes and fees

Seasonal outdoor pool, open 9:00 AM to 9 PM, pool umbrellas

13. Anchor Inn

Downtown Chincoteague, 1.8 mi from Deep Hole

rich

$101 nightly

Oct 4 - Oct 5

Total with taxes and fees

14. Birchwood Inn

Downtown Chincoteague, 2 mi from Deep Hole

Maryann

$85 nightly

Sep 17 - Sep 18

Total with taxes and fees

Palm Cottage | 1 bedroom, premium bedding, laptop workspace, soundproofing

15. Key West Cottages

Downtown Chincoteague, 1.2 mi from Deep Hole

Lindsay

$242 nightly

Sep 17 - Sep 18

Total with taxes and fees

16. Blufin Bungalows & Marina

Down the Marsh, 3.4 mi from Deep Hole

Angela

$181 nightly

Sep 23 - Sep 24

Total with taxes and fees

17. Best Western Plus Pocomoke City

14.7 mi from Deep Hole

alexis

$127 nightly

Sep 20 - Sep 21

Total with taxes and fees

18. Econo Lodge Pocomoke City Hwy 13

12.1 mi from Deep Hole

Deidre

$59 nightly

Oct 7 - Oct 8

Total with taxes and fees

19. Studio 6 Suites Pocomoke City, MD

13 mi from Deep Hole

Christina

$75 nightly

Sep 21 - Sep 22

Total with taxes and fees

20. Motel 6 Pocomoke City, MD

13 mi from Deep Hole

Debra

$70 nightly

Oct 1 - Oct 2

Total with taxes and fees

View all properties

Where to stay in Deep Hole

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

A horse grazing in a lush green field with a small stream.

Downtown Chincoteague

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

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Top Deep Hole Hotel Reviews

Waterside Inn

10/10 Excellent

"While this property was surely not perfect, the total experience was. The rooms are dated, not very clean, functional and asky rooms have a beautiful water view with a little b balcony. Even the elevator has windows and a water view. The staff is very friendly and accommodating. the breakfast is nice with a homey touch. We found this property to be an incredible value i"

Blufin Bungalows & Marina

8/10 Good

"Staying in a "floating" bungalow was unique. Warning to those with mobility issues: it is not very easy to get up and onto the porch. It was quite a long walk on narrow, floating piers to get to the bungalow we were staying in, then it's a large step up from the floating pier onto the porch, especially during low tide. Maybe those folks that take the reservations should ask customers if they have mobility issues before making the reservation."

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

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Deep Hole hotels

1. Comfort Suites Chincoteague Island Bayfront Resort

2. Atlantic Shores Inn and Suites

3. Spark by Hilton Chincoteague Island

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

5. Chincoteague Inn

6. Refuge Inn

7. Waterside Inn

8. Island Resort

9. Hampton Inn & Suites Chincoteague Waterfront

10. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

11. Days Inn by Wyndham Chincoteague Island

12. Maddox Inn

13. Anchor Inn

14. Birchwood Inn

15. Key West Cottages

16. Blufin Bungalows & Marina

17. Best Western Plus Pocomoke City

18. Econo Lodge Pocomoke City Hwy 13

19. Studio 6 Suites Pocomoke City, MD

20. Motel 6 Pocomoke City, MD

Where to stay in Deep Hole

Downtown Chincoteague

Piney Island

Snotty Ridge

Down the Marsh

Birch Town

Top Deep Hole Hotel Reviews

Waterside Inn

Frequently asked questions

Explore a world of travel with Expedia