Cheap Vacations in Isle of Wight County

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Isle of Wight County vacations

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $596, price is now $487 per person
$487
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $578, price is now $497 per person
$497
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $901, price is now $777 per person
$777
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was $675, price is now $582 per person
$582
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Blackbeard's Lodge

Blackbeard's Lodge

3.5 out of 5
Price was $714, price is now $622 per person
$622
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was $712, price is now $622 per person
$622
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Barrier Island Station

Barrier Island Station

2.5 out of 5
Price was $579, price is now $508 per person
$508
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $924, price is now $816 per person
$816
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $797, price is now $705 per person
$705
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was $633, price is now $565 per person
$565
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

3-night Isle of Wight County vacations

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $596, price is now $487 per person
$487
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Price was $546, price is now $518 per person
$518
per person
Dec 11 - Dec 14
found 4 hours ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $578, price is now $497 per person
$497
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Price was $675, price is now $582 per person
$582
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Blackbeard's Lodge

Blackbeard's Lodge

3.5 out of 5
Price was $714, price is now $622 per person
$622
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Price was $712, price is now $622 per person
$622
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Barrier Island Station

Barrier Island Station

2.5 out of 5
Price was $579, price is now $508 per person
$508
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $633, price is now $565 per person
$565
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Capes Hotel

The Capes Hotel

3 out of 5
Price was $583, price is now $527 per person
$527
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Va Beach-Oceanside (21st St) by IHG

Holiday Inn Va Beach-Oceanside (21st St) by IHG

3 out of 5
Price was $645, price is now $590 per person
$590
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $631, price is now $582 per person
$582
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Price was $768, price is now $712 per person
$712
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

4-night Isle of Wight County vacations

Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Price was $901, price is now $777 per person
$777
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Price was $1,024, price is now $881 per person
$881
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Price was $902, price is now $801 per person
$801
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Price was $883, price is now $814 per person
$814
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $979, price is now $905 per person
$905
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $1,002, price is now $927 per person
$927
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Price was $900, price is now $839 per person
$839
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
SpringHill Suites by Marriott Virginia Beach Oceanfront

SpringHill Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $1,021, price is now $958 per person
$958
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Chesapeake by IHG

Holiday Inn Express Hotel & Suites Chesapeake by IHG

2.5 out of 5
Price was $850, price is now $800 per person
$800
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Days Inn by Wyndham Chesapeake

Days Inn by Wyndham Chesapeake

2 out of 5
Price was $863, price is now $813 per person
$813
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express & Suites VA Beach Oceanfront by IHG

Holiday Inn Express & Suites VA Beach Oceanfront by IHG

3.5 out of 5
Price was $925, price is now $871 per person
$871
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

3 out of 5
Price was $904, price is now $854 per person
$854
per person
Nov 25 - Nov 29
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

5-night Isle of Wight County vacations

Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Price was $583, price is now $452 per person
$452
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Price was $762, price is now $611 per person
$611
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Price was $918, price is now $752 per person
$752
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Price was $576, price is now $485 per person
$485
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $640, price is now $556 per person
$556
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Capes Hotel

The Capes Hotel

3 out of 5
Price was $582, price is now $509 per person
$509
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $714, price is now $626 per person
$626
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Price was $599, price is now $536 per person
$536
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

3 out of 5
Price was $558, price is now $502 per person
$502
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
Price was $554, price is now $503 per person
$503
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Days Inn by Wyndham Virginia Beach At The Beach

Days Inn by Wyndham Virginia Beach At The Beach

2 out of 5
Price was $527, price is now $483 per person
$483
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $634, price is now $581 per person
$581
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

6-7 night Isle of Wight County vacations

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Little Creek

Econo Lodge Little Creek

2 out of 5
Price was $651, price is now $586 per person
$586
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
Price was $1,504, price is now $1,252 per person
$1,252
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
Price was $717, price is now $626 per person
$626
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Norfolk

La Quinta Inn & Suites by Wyndham Norfolk

3 out of 5
Price was $758, price is now $662 per person
$662
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $924, price is now $816 per person
$816
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $797, price is now $705 per person
$705
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Price was $788, price is now $709 per person
$709
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $812, price is now $732 per person
$732
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Homewood Suites by Hilton Virginia Beach/Norfolk Airport

Homewood Suites by Hilton Virginia Beach/Norfolk Airport

3 out of 5
Price was $857, price is now $779 per person
$779
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Virginia Beach - Norfolk by IHG

Holiday Inn Virginia Beach - Norfolk by IHG

3 out of 5
Price was $1,022, price is now $936 per person
$936
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Price was $698, price is now $641 per person
$641
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
Price was $685, price is now $638 per person
$638
per person
Dec 6 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

Top places to visit in Isle of Wight County

A river curving through a landscape with dry grass fields, a dock with boats, and houses along the riverbank.
FlightsFlightsHotelsHotels

Smithfield

Smithfield
A rural road with a sign for Carrollton, a brick building, and lush greenery.
FlightsFlightsHotelsHotels

Carrollton

Carrollton

Flight deals to Isle of Wight County

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

Fri, Dec 4 - Sun, Dec 6
ATL
Atlanta
ORF
Norfolk
$149 Roundtrip, found 5 days ago
$149
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Atlanta to Norfolk, returning Sun, Dec 6, priced at $149 found 5 days ago
Thu, Oct 29 - Thu, Nov 5
MCO
Orlando
ORF
Norfolk
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Orlando to Norfolk, returning Thu, Nov 5, priced at $154 found 3 days ago
Thu, Nov 12 - Mon, Nov 16
JAX
Jacksonville
ORF
Norfolk
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Nov 12 from Jacksonville to Norfolk, returning Mon, Nov 16, priced at $164 found 5 days ago

Top rated hotels for your Isle of Wight County vacation

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Free Cancellation
Reserve now, pay when you stay
24.71 mi from city center
$92 nightly
The price is $105 total per night
$105 total
Oct 29 - Oct 30
Total with taxes and fees
Located in Williamsburg, Hilton Vacation Club The Historic Powhatan Williamsburg is in the historical district, a 4-minute drive from College of William and Mary and 6 minutes from Jamestown Settlement.
Pool
Parking included
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Free Cancellation
Reserve now, pay when you stay
27.46 mi from city center
$124 nightly
The price is $141 total per night
$141 total
Nov 5 - Nov 6
Total with taxes and fees
With a stay at Vacation Village At Williamsburg, you'll be centrally located in Williamsburg, within a 5-minute drive of Williamsburg Premium Outlets and College of William and Mary.
Pool
Kitchen
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr Williamsburg VA
Free Cancellation
Reserve now, pay when you stay
25.76 mi from city center
$117 nightly
The price is $135 total per night
$135 total
Oct 26 - Oct 27
Total with taxes and fees
A stay at Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel places you in the heart of Williamsburg, steps from Colonial Williamsburg Visitor Center and a 3-minute drive from Merchants Square.
Pool
Breakfast included
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.