Chesapeake Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Chesapeake Vacation

Say bye-bye to planning worries and hello to a Chesapeake vacation package. With everything organized before you leave, you can focus on discovering every inch of this city, starting with Burlington, which is good for history, dining and shopping. You'll want to sightsee during your trip to Chesapeake. Make time for big-name attractions such as Huntington Museum of Art, Keith Albee Theatre and Mountain Health Arena. Don't delay your visit to this city any longer. Your perfect Chesapeake vacation is a few quick clicks away with Expedia.

Ready to book your vacation to Chesapeake?

 

Choose your dates

Chesapeake Hotel Deals

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

4 out of 5
1001 3rd Avenue Huntington WV
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from May 3 to May 4
CA $145
CA $164 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Breakfast was very good, would recommend to other travelers.

Reviewed on Apr 13, 2026

DoubleTree by Hilton Huntington
Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

3 out of 5
10945 Route 60 Ashland KY
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Apr 26 to Apr 27
CA $128
CA $145 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (753 reviews)
Inspite of that We checked in late, they did not clean our bedroom upon arrival, there were hairs all over the bathroom sink, dirty toilet seat, brown-looking stained sheets and the carpet was visibly not vaccumed , it was a very disappointing experience. We called front desk for a refund but they ...

Reviewed on Apr 17, 2026

Fairfield Inn & Suites By Marriott Ashland
Delta Hotels by Marriott Huntington Downtown

Delta Hotels by Marriott Huntington Downtown

3 out of 5
800 3rd Ave Huntington WV
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Apr 26 to Apr 27
CA $177
CA $200 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Clean room , bed was so comfortable and the pillows were perfect for my husband. He loves a super soft pillow. Shower was amazing and the room temperature stayed perfect.

Reviewed on Apr 10, 2026

Delta Hotels by Marriott Huntington Downtown
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.