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Deep Hole Vacation Packages

Deep Hole Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

3.5 out of 5
Northeast Virginia Beach
Price was $401, price is now $349 per person
$349
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Stay at this 3.5-star beach hotel in Virginia Beach. Enjoy free WiFi, 2 indoor pools, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Ocean Breeze Waterpark are located nearby.
The Sanderling

The Sanderling

4 out of 5
Price was $1,246, price is now $801 per person
$801
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Stay at this 4-star beach hotel in Kitty Hawk. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Sanderling Spa and Nor'Banks Sailing are located nearby.
Ramada Plaza by Wyndham Nags Head Oceanfront

Ramada Plaza by Wyndham Nags Head Oceanfront

3 out of 5
Price was $466, price is now $371 per person
$371
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Book a stay at this beach hotel in Kill Devil Hills. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Destination Fun and OBX Laser Tag are located nearby.
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Price was $1,151, price is now $930 per person
$930
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
Stay at this 4-star business-friendly hotel in Norfolk. Enjoy 3 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Waterside District and Greenbrier Mall are located nearby.
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $1,063, price is now $871 per person
$871
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
Stay at this 4-star B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Waterside District and Pagoda and Oriental Garden are located nearby.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Price was $649, price is now $532 per person
$532
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Holiday Inn Newport News - Hampton by IHG

Holiday Inn Newport News - Hampton by IHG

3.5 out of 5
Central Newport News
Price was $666, price is now $560 per person
$560
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
Stay at this 3.5-star business-friendly hotel in Newport News. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Hampton Coliseum and Cinemark City Center are located nearby.
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
Downtown Norfolk
Price was $675, price is now $572 per person
$572
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Norfolk. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Waterside District and Greenbrier Mall are located nearby.

3-4 Night Vacations in Deep Hole

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Nags Head Oceanfront

Ramada Plaza by Wyndham Nags Head Oceanfront

3 out of 5
Price was $466, price is now $371 per person
$371
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Price was $1,246, price is now $801 per person
$801
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
Coliseum Central
Price was $625, price is now $536 per person
$536
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Price was $1,053, price is now $907 per person
$907
per person
Dec 5 - Dec 9
found 2 days ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)

5-7 Night Vacations in Deep Hole

Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Price was $649, price is now $532 per person
$532
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Price was $1,697, price is now $1,318 per person
$1,318
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Norfolk (ORF)
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Price was $1,151, price is now $930 per person
$930
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $1,063, price is now $871 per person
$871
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)

Cheap Hotel Deals in Deep Hole

Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Stay at this hotel in Chincoteague. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Opens in a new windowWaterside Inn
Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 out of 5
4195 Main St, Chincoteague, VA
Stay at this hotel in Chincoteague. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowComfort Suites Chincoteague Island Bayfront Resort
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St, Chincoteague, VA
Stay at this 3-star vacation home in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Chincoteague Channel and Assateague ...
Opens in a new windowBlufin Bungalows & Marina
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Refuge Inn

Refuge Inn

3 out of 5
7058 Maddox Blvd., Chincoteague, VA
Stay at this 3-star business-friendly hotel in Chincoteague. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowRefuge Inn
Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

2.5 out of 5
3801 Main St, Chincoteague, VA
Book a stay at this business-friendly hotel in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
Opens in a new windowMarina Bay Hotel & Suites, an Ascend Collection Hotel
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street, Chincoteague, VA
Stay at this 3-star cottage in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
Opens in a new windowKey West Cottages
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road, Chincoteague, VA
Stay at this motel in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowChincoteague Inn
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

2.5 out of 5
125 Newtowne Blvd, Pocomoke City, MD
Book a stay at this business-friendly hotel in Pocomoke City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Opens in a new windowBest Western Plus Pocomoke City
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 6 - Sun, Nov 9
MCO
Orlando Intl.
ORF
Norfolk Intl.
$78 Roundtrip, found 3 hours ago
$78
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Orlando Intl. to Norfolk Intl., returning Sun, Nov 9, priced at $78 found 3 hours ago
Spirit Airlines
Sat, Oct 25 - Mon, Nov 3
TPA
Tampa Intl.
ORF
Norfolk Intl.
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Oct 25 from Tampa Intl. to Norfolk Intl., returning Mon, Nov 3, priced at $142 just found
Frontier Airlines
Wed, Nov 26 - Mon, Dec 8
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$146 Roundtrip, found 3 hours ago
$146
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Nov 26 from Dallas-Fort Worth Intl. to Norfolk Intl., returning Mon, Dec 8, priced at $146 found 3 hours ago
Spirit Airlines
Thu, Nov 13 - Mon, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$149 Roundtrip, found 4 hours ago
$149
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Mon, Nov 17, priced at $149 found 4 hours ago