Deep Hole Vacations from $467

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Your Deep Hole Vacation

Take the stress out of organizing your next exciting adventure with a Deep Hole vacation package. Whether you've come for its history, food or something else, there's an inexhaustible array of experiences to be had. Fill your itinerary with tours of Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Oyster Bay, some of the things you shouldn't miss during your trip to Deep Hole. Browse Expedia's wide range of travel options and book your dream vacation to Deep Hole today.

The Latest Deep Hole Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Boardwalk Resort and Villas

Northeast Virginia Beach

$467

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

8.8/10 Excellent! (1,006 reviews)

Boardwalk One

Downtown Ocean City

$1,180

per person

Nov 15 - Nov 18

found 21 hours ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

7.4/10 Good! (178 reviews)

The room was fresh cleaned, hot showers and plenty of space. Staff was very nice and informative. We were able to have covered parking. We watched the major storm with the high waves and wind from balcony but didn't disturb us with doors closed. Location was great for walking boardwalk. When too wet had an excellent tv and reception in the room.

Reviewed on Sep 28, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$586

per person

Dec 3 - Dec 7

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

8.2/10 Very Good! (1,417 reviews)

Great stay

Reviewed on Oct 1, 2026

The Colony at Virginia Beach

Northeast Virginia Beach

$858

per person

Nov 10 - Nov 16

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

9.2/10 Wonderful! (52 reviews)

Fenwick Shores, Tapestry Collection by Hilton

$874

per person

Nov 1 - Nov 8

found 7 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Salisbury (SBY)

9.4/10 Exceptional! (851 reviews)

This is a hotel with very comfortable rooms and a beautiful lobby. The best feature is that it is walking distance to the Fenwick Island Beach, a beautiful quiet tranquil ocean. One recommendation I have is to provide more options for breakfast. It also could’ve been that we came during an un-busy time, the week of September 28, which is after the busy season. Other than that, I would highly recommend this hotel, especially if you want to get away from the busyness of Rehoboth.

Reviewed on Oct 1, 2026

Where to stay in Deep Hole

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

A field of horses near a body of water with a crowd in the background.

Downtown Chincoteague

2 out of top 10 points of interest in this area

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

A coastal landscape with a clear blue sky, a calm sea, and a marshy area with water reflecting the sky.

Piney Island

2 out of top 10 points of interest in this area

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

1 out of top 10 points of interest in this area

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 Assateague Point.

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.

Deep Hole Hotel Deals

Oyster Catcher | Deep Creek Waterfront w/ Deep Water Dock, Screened Porch, Guest Cottage & Pets

Chincoteague Island VA

9/10 Wonderful! (6 reviews)

"Old and lovely house, great dock, pets allowed, kayaking access, roomy parking. We love Oyster Catcher!"

Reviewed on Sep 5, 2026

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Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly

Chincoteague Island VA

9/10 Wonderful! (6 reviews)

"Cozy and hidden away from the main road. Plenty of room for dogs to roam around."

Reviewed on Jul 13, 2026

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Cozy 2-bedroom house in Chincoteague

Chincoteague VA

$269 nightly

$302 total

Oct 4 - Oct 5

Total with taxes and fees

10/10 Exceptional! (6 reviews)

"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 ..."

Reviewed on Aug 7, 2026

See all 750 properties in Deep Hole

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.