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.
Club Wyndham Kingsgate
3.0-star property

Club Wyndham Kingsgate

8.8/10 Excellent! (1,019 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $883, price is now $651 per person
$651
per person
found 7 hours 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

The Colonies at Williamsburg
3.0-star property

The Colonies at Williamsburg

9/10 Wonderful! (1,032 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,049, price is now $670 per person
$670
per person
found 7 hours ago
Need hand rails in shower

Reviewed on Aug 27, 2024

Williamsburg Inn, an official Colonial Williamsburg Hotel
5.0-star property

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg
9.8/10 Exceptional! (349 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,714, price is now $1,193 per person
$1,193
per person
found 7 hours ago
Williamsburg Inn is truly a 5-star resort experience! From the incredible staff to the beautiful property, can’t ask for anything more. Thanks again for another amazing stay!

Reviewed on Nov 2, 2023

Club Wyndham Governor’s Green
3.0-star property

Club Wyndham Governor’s Green

9.2/10 Wonderful! (248 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,156, price is now $825 per person
$825
per person
found 7 hours ago
Would recommend this property to anyone! It was quiet and very clean. Our kiddos loved playing at the ping pong tables and throwing the footballs in the grass areas. We will definitely be back.

Reviewed on Oct 19, 2025

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

Holiday Inn Club Vacations Williamsburg Resort by IHG

9/10 Wonderful! (562 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,613, price is now $1,177 per person
$1,177
per person
found 7 hours 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

Embassy Suites Williamsburg
3.5-star property

Embassy Suites Williamsburg

8.4/10 Very Good! (1,011 reviews)

Jul 12 - Jul 18

6 night stay

Boston (BOS) to Richmond (RIC)

JetBlue Airways • Roundtrip • Coach
Price was $904, price is now $669 per person
$669
per person
found 7 hours ago
Southern hospitality shines in this hotel! Everyone from the front desk to maintenance personnel were friendly. Nicest hotel stay I’ve had in years.

Reviewed on Jul 10, 2025

Hotel deals near Chesapeake Bay

Shore Stay Suites

Shore Stay Suites

2 out of 5
26406 Lankford Hwy Cape Charles VA
Free Cancellation
Reserve now, pay when you stay
22.36 mi from Chesapeake Bay
$116 nightly
The price is $129 total per night
$129 total
Apr 26 - Apr 27
Total with taxes and fees
Shore Stay Suites features free WiFi in public areas, a terrace, and laundry facilities. You can put free parking to good use if you drive. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include barbecue grills, a vending machine, and a picnic area.
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
45.88 mi from Chesapeake Bay
$150 nightly
The price is $175 total per night
$175 total
May 4 - May 5
Total with taxes and fees
Guests of Hyatt Place Virginia Beach / Oceanfront enjoy a 24-hour gym, free WiFi in public areas, and conference space. Valet parking is available for USD 15 per night, and there's also a beach shuttle. The front desk is staffed 24/7 to help with dry cleaning/laundry, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a 24-hour business center, a seasonal outdoor pool, and a microwave in a common area.
Pool
Breakfast included
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Free Cancellation
Reserve now, pay when you stay
36.82 mi from Chesapeake Bay
$98 nightly
The price is $114 total per night
$114 total
Apr 26 - Apr 27
Total with taxes and fees
At Embassy Suites by Hilton Hampton Convention Center, guests enjoy features like an indoor pool, a 24-hour gym, and WiFi in public areas. Valet parking is offered for USD 22 per day. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, luggage storage, and securing valuables. Other amenities at this family-friendly hotel include a conference center, a business center, and a computer station.
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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.