Package deals near Chesapeake Bay

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Top Chesapeake Bay vacation deals

Price found within the past 48 hours. Click for updated prices.
Wedmore Place
3.5-star property

Wedmore Place

9.2/10 Wonderful! (1,000 reviews)

Dec 27 - Dec 31

4 night stay

Chicago (ORD) to Richmond (RIC)

United • Roundtrip • Coach
Price was $734, price is now $589 per person
$589
per person
found 18 hours ago
Great place to stay while visiting Williamsburg and the rest of the area. Williamsburg Winery on site was great. Room was nice as well. The decor was cool. Bathroom and TV were a little dated but we never used the TV. Bathroom in our particular room could use some updating, but nothing that took away from the overall experience. It has the feel of a place that could be really awesome with some freshening.

Reviewed on Oct 20, 2026

Westgate Historic Williamsburg Resort
3.5-star property

Westgate Historic Williamsburg Resort

Midtown
8.6/10 Excellent! (1,001 reviews)

Dec 10 - Dec 14

4 night stay

Denver (DEN) to Richmond (RIC)

United • Coach

Richmond (RIC) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,106, price is now $677 per person
$677
per person
found 1 day ago
A short but very enjoyable stay.

Reviewed on Oct 20, 2026

The Commonwealth
4.0-star property

The Commonwealth

Downtown Richmond
8.8/10 Excellent! (1,407 reviews)

Nov 25 - Nov 30

5 night stay

Chicago (ORD) to Richmond (RIC)

American Airlines • Coach

Richmond (RIC) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,147, price is now $816 per person
$816
per person
found 5 hours ago
Overall impression was an old bldg made newish Narrow halls, tiny elevators, street in front blocked off, no free guest parking and nice, helpful extremely weird looking staff at check- out Beds were comfortable and 2 flat screen tvs were a Plus Probably would not stay there again!

Reviewed on Oct 19, 2026

Wingate by Wyndham Richmond Short Pump
3.0-star property

Wingate by Wyndham Richmond Short Pump

Short Pump
8.4/10 Very Good! (1,707 reviews)

Nov 25 - Nov 30

5 night stay

Chicago (ORD) to Richmond (RIC)

American Airlines • Coach

Richmond (RIC) to Chicago (ORD)

Frontier Airlines • Coach
Price was $831, price is now $658 per person
$658
per person
found 5 hours ago
Checkin staff was great. Couldn't use A/C in room because of noise it made. Glad it was cool outside and fan worked. One Elevator didn't work. The one that did was very dirty. Halls and doors need freshening up. Parking great. Location good.

Reviewed on Oct 19, 2026

The Colonies at Williamsburg
3.0-star property

The Colonies at Williamsburg

9/10 Wonderful! (1,135 reviews)

Dec 27 - Dec 31

4 night stay

Chicago (ORD) to Richmond (RIC)

United • Roundtrip • Coach
Price was $805, price is now $638 per person
$638
per person
found 18 hours ago
I enjoyed the property and loved that it was close to everything. There were 2 things I wasn’t happy with, the pool and parking. It was advertised that the pool was heated but it was cold. I came back after 9pm and there was no parking. They had an overflow parking lot but some vacationers didn’t follow directions to park 2nd vehicles in that area. Other than those things, I had a wonderful stay!

Reviewed on Oct 22, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel
3.0-star property

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg
8.8/10 Excellent! (889 reviews)

Dec 27 - Dec 31

4 night stay

Chicago (ORD) to Richmond (RIC)

United • Roundtrip • Coach
Price was $776, price is now $644 per person
$644
per person
found 18 hours ago

Hotel deals near Chesapeake Bay

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

2.5 out of 5
3446 Lankford Hwy Exmore VA
Free Cancellation
14.96 mi from Chesapeake Bay
The price is $104 total per night
$104 total
per night
Oct 29 - Oct 30
Guests of Holiday Inn Express & Suites Exmore - Eastern Shore by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with luggage storage and securing valuables. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Breakfast included
Waterfront Oasis with Crabs, Oysters and Mother Nature

Waterfront Oasis with Crabs, Oysters and Mother Nature

Hacksneck VA
14.97 mi from Chesapeake Bay
Get rates
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Beachfront Estate, Multi-Level Decks, Bay Creek

Beachfront Estate, Multi-Level Decks, Bay Creek

Cape Charles VA
19.51 mi from Chesapeake Bay
Get rates
This vacation home offers a water park, a gym, and laundry facilities. Other amenities at this beach vacation home include barbecue grills and a garden.
Pool
Kitchen
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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.