Search Deals onChesapeake Vacation Packages
Chesapeake Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Boardwalk Resort and Villas
Price was $548, price is now $467 per person
$467
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this 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 First Landing State Park are located nearby.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Price was $636, price is now $536 per person
$536
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach aparthotel 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 First Landing State Park are located nearby.

The Colony at Virginia Beach
Price was $616, price is now $524 per person
$524
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach condo in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
The place was centrally located on the boardwalk. The pier was directly to the left but right there to look at. We saw dolphins every day while sitting on the balcony. The parking was a tight fit for a supercrew truck, but they went out of their way to accommodate me in parking spot that worked. Very friendly to speak with even prior to arrival and while there. All staff were very friendly. The kitchen is fully furnished. Even came with a keurig and a regular coffee maker. Dish soap, towels, etc. Middle od f the week was a complimentary ice cream social. There is a area in the bldg. where you can get games, books, puzzles, etc and take back to your place. We were very pleased and will definitely stay again. We visited in Oct 2026. It’s the off season and the rates were lower. The weather was great and it was not crowded at all. This was the bonus, not crowded. There were plenty of restaurants to drive or walk to and eat out. Check out The restaurant next door at Jumpin Shrimp. We ate there several times and they have an awesome happy hour for giant size wings. The best wings I’ve had in a long time. I went there twice for wings within 5 days. Drink specials too! I will be back!
Reviewed on Oct 31, 2026

The Burrus House Inn Waterfront Suites
Price was $1,098, price is now $950 per person
$950
per person
Dec 17 - Dec 21
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Norfolk (ORF)
Stay at this B&B in Manteo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Roanoke Marshes Lighthouse and Dare County Arts Council are located nearby.
We stayed at the Burrus House for four nights and it was perfect! The staff was awesome -everyone we met or ran into was extremely helpful and friendly. The cleanliness of the whole hotel from the office to our room and the entertainment area was impeccable. Everything about the hotel and our stay was wonderful. I highly recommend the Burrus House!!
Reviewed on Oct 24, 2026

Hyatt House Virginia Beach / Oceanfront
Price was $901, price is now $783 per person
$783
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
The property is Ocean Front. And the views are stunning. The staff was friendly, extremely helpful with suggestions for area activities and restaurants. Breakfast was until 10:30 so sleeping in was an option and they continued to bring hot food out until that time.
Reviewed on Nov 4, 2026

Holiday Inn Va Beach-Oceanside (21st St) by IHG
Price was $608, price is now $530 per person
$530
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.

The Barclay Towers Resort Hotel
Price was $586, price is now $515 per person
$515
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this 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 First Landing State Park are located nearby.
Cool stay. Staff was very cool.
Reviewed on Nov 2, 2026

Marriott Virginia Beach Oceanfront Resort
Price was $727, price is now $643 per person
$643
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
The Marriott/Cavalier hotel was excellent. Clean spacious room, staff was great, oceanfront, perfect!!!!. Prepare to pay for parking daily. Restaurants nearby. I would stay here again.
Reviewed on Nov 4, 2026
Chesapeake Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Chesapeake Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Dec 9 - Fri, Dec 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago

Wed, Dec 9 - Mon, Dec 14
TPA
Tampa Intl.
ORF
Norfolk Intl.
$132 Roundtrip, found 6 hours ago
$132
Roundtrip
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Thu, Jan 7 - Tue, Jan 12
MCO
Orlando Intl.
ORF
Norfolk Intl.
$135 Roundtrip, found 6 hours ago
$135
Roundtrip
found 6 hours ago

Sat, Dec 5 - Sat, Dec 12
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$206 Roundtrip, found 6 hours ago
$206
Roundtrip
found 6 hours ago
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