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.
Vacation Village At Williamsburg
3.0-star property

Vacation Village At Williamsburg

8.8/10 Excellent! (1,732 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $440, price is now $335 per person
$335
per person
found 1 day ago
Great location and friendly staff!

Reviewed on Sep 18, 2025

The Colonies at Williamsburg
3.0-star property

The Colonies at Williamsburg

9/10 Wonderful! (1,002 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $609, price is now $442 per person
$442
per person
found 1 day ago
Need hand rails in shower

Reviewed on Aug 27, 2024

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3.0-star property

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg
8.8/10 Excellent! (1,568 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $456, price is now $345 per person
$345
per person
found 1 day ago
The location of this hotel is very convenient if you are planning on exploring the historical sites in Williamsburg as it is right next to the visitor center. The location is somewhat remote so in the evening it is dark and scary to be outside. The parking lots are not very well lit or in good condition. We were given a very smelly room as we were traveling with our emotional support dog. There are no exhaust fans in the bathrooms, so everything in the bathroom travels into the bedroom and stays there. There are dehumidifiers in every room, which are very loud and don’t add a positive touch to the experience. The stuff is very friendly and knowledgeable so five stars for that. The breakfast is very limited with mostly dry goods. The coffee is awful. Do not recommend.

Reviewed on Aug 14, 2025

Club Wyndham Governor’s Green
3.0-star property

Club Wyndham Governor’s Green

9.2/10 Wonderful! (222 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $523, price is now $398 per person
$398
per person
found 1 day ago
The check in process was easy and efficient. The grounds themselves are well maintained. The room was spacious and clean! Overall, we would recommend this resort to anyone.

Reviewed on Nov 5, 2021

Holiday Inn Club Vacations Williamsburg Resort by IHG
3.5-star property

Holiday Inn Club Vacations Williamsburg Resort by IHG

9/10 Wonderful! (504 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $445, price is now $341 per person
$341
per person
found 1 day ago
My family have stayed at this property before so we knew what to expect. We were even more impressed! We stayed in one of the newer buildings. The unit (2bd w/ 1 queen and 1 full sz beds) was larger than our previous room. Convenient amenities for family fun. Excellent location, no more than 5-10 mins for all "necessities" (i.e. Walmart, Outlets, eateries, amusement parks etc :)! We had a great time!

Reviewed on Dec 31, 2023

Wedmore Place
3.5-star property

Wedmore Place

9.6/10 Exceptional! (1,007 reviews)

Dec 17 - Dec 20

3 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Coach

Richmond (RIC) to Boston (BOS)

United • Coach
Price was $539, price is now $422 per person
$422
per person
found 1 day ago
Loved our stay and will be back!

Reviewed on Apr 28, 2025

Hotel deals near Chesapeake Bay

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
2800 Shore Drive, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
42.02 mi from Chesapeake Bay
$89 nightly
The price is $104 total per night
$104 total
Nov 16 - Nov 17
Total with taxes and fees
Renovated in 2020, Delta Hotels by Marriott Virginia Beach Waterfront Suites offers a 24-hour gym, free WiFi in public areas, and conference space. Valet parking is available for USD 35 per day. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Pool
Pet friendly
Onley Inn

Onley Inn

2 out of 5
25297 Lankford Hwy, Onley, VA
Free Cancellation
Reserve now, pay when you stay
24.3 mi from Chesapeake Bay
$77 nightly
The price is $83 total per night
$83 total
Oct 19 - Oct 20
Total with taxes and fees
At Onley Inn, guests have access to free WiFi in public areas, conference space, and an arcade/game room. Free extended parking is available if you drive. The 24-hour front desk has staff always at the ready. This hotel also has a banquet hall.
Pet friendly
Parking included
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Free Cancellation
Reserve now, pay when you stay
36.05 mi from Chesapeake Bay
$81 nightly
The price is $95 total per night
$95 total
Nov 2 - Nov 3
Total with taxes and fees
At Comfort Inn & Suites Hampton near Coliseum, guests enjoy an indoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
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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.