Package deals near Chesapeake Bay

Save more on your trip when booking your flight + hotel together

Top Chesapeake Bay vacation deals

Price found within the past 48 hours. Click for updated prices.
Patriots Inn
2.5-star property

Patriots Inn

9.4/10 Exceptional! (1,010 reviews)

Jul 31 - Aug 4

4 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $519, price is now $407 per person
$407
per person
found 1 day ago
Front desk worked withour reservation. Room was spotless. Also huge a king bed and shower and a pull out queen. Comforable. And a second full bath. Kitchenette was complete. Only thing i would recommend was better coffee!.

Reviewed on Nov 17, 2025

Hilton Richmond Downtown
4.0-star property

Hilton Richmond Downtown

Downtown Richmond
8.2/10 Very Good! (1,000 reviews)

Jul 16 - Jul 20

4 night stay

Orlando (MCO) to Richmond (RIC)

Frontier Airlines • Coach

Richmond (RIC) to Orlando (MCO)

American Airlines • Coach
Save 100% on your flight
Price was $1,136, price is now $808 per person
$808
per person
found 18 hours ago
Great location and room, valet parking charged our EV, staff very helpful w/ a forgotten toothbrush and bag storage, thumbs up.

Reviewed on Apr 21, 2026

Wingate by Wyndham Richmond Short Pump
3.0-star property

Wingate by Wyndham Richmond Short Pump

Short Pump
8.4/10 Very Good! (1,845 reviews)

Jul 31 - Aug 4

4 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $601, price is now $455 per person
$455
per person
found 16 hours ago
Property was nice and clean. However, the elevator did not function properly. I was trapped inside for a few minutes and my wife was also trapped for a few minutes the next day. When she hit the call button, maintenance gave her a 45-minute eta.

Reviewed on Mar 21, 2026

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
3.0-star property

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

9/10 Wonderful! (1,001 reviews)

Jul 31 - Aug 4

4 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $569, price is now $438 per person
$438
per person
found 1 day ago
Clean room, good breakfast,

Reviewed on Mar 9, 2026

Hilton Richmond Hotel & Spa/Short Pump
4.0-star property

Hilton Richmond Hotel & Spa/Short Pump

Short Pump
8.8/10 Excellent! (1,007 reviews)

Jul 31 - Aug 4

4 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $665, price is now $523 per person
$523
per person
found 16 hours ago
Beautiful property! I would certainly recommend this hotel.

Reviewed on Oct 4, 2025

Club Wyndham Kingsgate
3.0-star property

Club Wyndham Kingsgate

8.8/10 Excellent! (1,004 reviews)

Jul 31 - Aug 4

4 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $548, price is now $439 per person
$439
per person
found 1 day ago
Lots of fun things for kids to do and everyone was friendly loved that add one we’re all included so kids could enjoy it all

Reviewed on Nov 4, 2024

Hotel deals near Chesapeake Bay

Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
12.93 mi from Chesapeake Bay
$381 nightly
The price is $444 total per night
$444 total
May 26 - May 27
Total with taxes and fees
Guests of this cottage enjoy features like a gym, a hot tub, and laundry facilities.
Hot Tub
Kitchen
Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy Exmore VA
Free Cancellation
Reserve now, pay when you stay
15.04 mi from Chesapeake Bay
$93 nightly
The price is $104 total per night
$104 total
Jun 1 - Jun 2
Total with taxes and fees
At Hampton Inn & Suites Exmore - Eastern Shore, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with securing valuables and dry cleaning/laundry. Additional amenities include conference space, a business center, and coffee/tea in a common area.
Pool
Breakfast included
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
44.54 mi from Chesapeake Bay
$94 nightly
The price is $110 total per night
$110 total
May 25 - May 26
Total with taxes and fees
Guests staying at Wyndham Virginia Beach Oceanfront enjoy an indoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Other amenities at this beach hotel include meeting rooms, a conference center, and a business center.
Pool
Pet friendly
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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.

Book a Chesapeake Bay vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Chesapeake Bay, now is the perfect time. Book your getaway to with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing  sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Chesapeake Bay, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Chesapeake Bay vacation. Book your  package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Chesapeake Bay any longer. Save a bundle and book your  escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.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.