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Chesapeake Vacation Packages

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Chesapeake Flight + Hotel Packages

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

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $667, price is now $439 per person
$439
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star beach hotel in Kill Devil Hills. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Professor Hacker's Lost Treasure Golf and Avalon Fishing Pier are located nearby.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,009, price is now $578 per person
$578
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Kill Devil Hills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Destination Fun and OBX Laser Tag are located nearby.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Save 100% on your flight
Price was $1,023, price is now $595 per person
$595
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star beach hotel in Virginia Beach. Enjoy free WiFi, free parking, 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.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Save 100% on your flight
Price was $722, price is now $441 per person
$441
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach are located nearby.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $5,955, price is now $4,000 per person
$4,000
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 4-star beach resort in Kitty Hawk. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Popular attractions The Sanderling Spa and Nor'Banks Sailing are located nearby.
Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Save 100% on your flight
Price was $851, price is now $612 per person
$612
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3.5-star golf condo in Kitty Hawk. Enjoy free parking, 2 outdoor pools, and a fitness center. Popular attractions Sea Scape Golf Links and Monument to a Century of Flight are located nearby.
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Save 100% on your flight
Price was $1,920, price is now $1,401 per person
$1,401
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Outer Banks Beach Club

Outer Banks Beach Club

2.5 out of 5
Save 100% on your flight
Price was $720, price is now $527 per person
$527
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Kill Devil Hills. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Destination Fun and Stop-N-Shop Beach Shop are located nearby.

Chesapeake Vacation Packages 3-4 Night Stays

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

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $488, price is now $328 per person
$328
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $3,097, price is now $2,172 per person
$2,172
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $534, price is now $383 per person
$383
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Norfolk (ORF)
Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Price was $605, price is now $443 per person
$443
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

Chesapeake Vacation Packages 5-7 Night Stays

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

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $667, price is now $439 per person
$439
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,009, price is now $578 per person
$578
per person
Oct 14 - Oct 21
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
Save 100% on your flight
Price was $1,023, price is now $595 per person
$595
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $722, price is now $441 per person
$441
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

Top Flight Deals

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

Breeze Airways
Sat, Sep 27 - Mon, Sep 29
TPA
Tampa Intl.
ORF
Norfolk Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 27 from Tampa Intl. to Norfolk Intl., returning Mon, Sep 29, priced at $107 found 1 day ago
Breeze Airways
Fri, Sep 26 - Mon, Sep 29
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 26 from Jacksonville Intl. to Norfolk Intl., returning Mon, Sep 29, priced at $107 found 1 day ago
Frontier Airlines
Thu, Sep 18 - Thu, Sep 25
MCO
Orlando Intl.
ORF
Norfolk Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Orlando Intl. to Norfolk Intl., returning Thu, Sep 25, priced at $110 found 2 days ago
Frontier Airlines
Tue, Oct 21 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Oct 21 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Sat, Oct 25, priced at $144 found 2 days ago