Chesapeake Bay Holidays

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Your Chesapeake Bay Holiday

Make planning your next getaway easy with a Chesapeake Bay holiday package. Whether it's the history, cuisine or something else entirely that lures you to this destination, our package deals will help you experience it all. With so much to explore on a trip to Chesapeake Bay, it can be difficult to know where to begin. Kick off your travels in Washington at AFI Silver Theatre and Washington Golf and Country Club — two popular family-friendly attractions here. Another city worth adding to your itinerary is Baltimore. Sweethearts seeking a romantic escape here shouldn't miss Hippodrome Theatre and Captain James Landing. Whether you plan to travel on a budget or in the lap of luxury, Expedia are here to help you customize your next Chesapeake Bay holiday.

Chesapeake Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)

Our guide on where to stay in Chesapeake Bay

Check out a few of the areas and neighbourhoods we love in Chesapeake Bay Learn more about Chesapeake Bay

Our pick of the best Chesapeake Bay Hotel Deals

Hotel Pentagon
Hotel Pentagon
3 out of 5
2480 S Glebe Rd, Arlington, VA
Stay at this hotel in Arlington. Enjoy free breakfast, free WiFi and free parking. Our guests praise the clean rooms and the overall value in their reviews. ...
6.4/10 (1,120 reviews)
"No frills but perfectly adequate - price is right, and very convenient for traveling professionals not spending a ton of time on property."

Reviewed on 23 Apr 2024

Hotel Pentagon
Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
Stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool and breakfast. Our guests praise the breakfast and the pool in their reviews. ...
8.6/10 Excellent! (3,152 reviews)
A remarkable stay
"It was an amazing stay and I enjoyed myself at your beautiful hotel."

Reviewed on 22 Apr 2024

Washington Plaza Hotel
Omni Shoreham Hotel
Omni Shoreham Hotel
4 out of 5
2500 Calvert St Nw, Washington, DC
Stay at this business-friendly hotel in Washington. Enjoy an outdoor pool, 2 bars/lounges and breakfast. Our guests praise the breakfast and the pool in their ...
8.4/10 Very Good! (1,218 reviews)
"This was a wonderful experience for my friend and I. Annett and Qazi in dining were wonderful and VERY welcoming. Crystal at the front desk was amazing, her welcome smiling and how she treated us when we arrived was profound. DEBORAH at the front desk had too much ATTITUDE for our liking when we ..."

Reviewed on 22 Apr 2024

Omni Shoreham Hotel
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.

Frequently asked questions

Why should I book my Chesapeake Bay holiday with Expedia?
Expedia has you covered for all aspects of your next Chesapeake Bay trip. You’ll always get the best deal possible, but when you bundle your airfares, accommodation and/or hire car into a holiday package, you’ll save even more. Looking to really make the most of your adventure? Add some awesome activities and tours to your customised package. We offer flexible cancellation policies on most bookings, so there’s no need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Chesapeake Bay?
Chesapeake Bay gets busy in March, May and July. If you don’t like crowds and prefer a more relaxed pace, lock in your escape for January, October and December. With average daytime temperatures of 1ºC, January is the coolest period in Chesapeake Bay. The warmest time of year is July, when you can experience averages of 25ºC throughout the day. Whatever the temperature, you’ll discover plenty to keep you occupied here.
What are the top hotels for my holiday in Chesapeake Bay?
For properties in Ocean City with friendly service and comfortable beds, check out Courtyard by Marriott Baltimore Downtown/McHenry Row and Clarion Hotel BWI Airport Arundel Mills. If you’re visiting Washington as well, you can look forward to a wonderful night’s sleep at Arlo Midtown or Holiday Inn Manhattan-Financial District, an IHG Hotel.
How do I get a cheap holiday to Chesapeake Bay?
Booking a hotel and flight together with Expedia won’t just save valuable time — it’ll save you money too. A Chesapeake Bay holiday makes it simple to arrange the ideal trip. With more than 400 airlines across the world to choose from, finding flights that suit your busy schedule won’t be a challenge. On top of that, we’ve got over 321,000 properties globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia puts more of the world within your reach. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Chesapeake Bay holiday?
Plan your holiday in Chesapeake Bay around well-known attractions like White House and Arlington National Cemetery. Many tourists also recommend National Aquarium in Baltimore and Washington Monument.
What are the best cities to stay in when on holiday in Chesapeake Bay?
To see terrific attractions such as U.S. Naval Academy and Six Flags America, Annapolis is the place to be. Lots of travellers also rave about College Park, home to University of Maryland, College Park and Maryland Stadium. If time is on your side, why not check out both cities?
Do I need a visa for my Chesapeake Bay holiday?
Visa requirements for Chesapeake Bay vary depending on your nationality and the reason for your visit. It’s wise to check official government websites to determine if you need a visa for your trip. They’ll give you the most up-to-date information, including details about application procedures or any supporting documentation you may need. Research your visa requirements well ahead of time to ensure a travel experience that’s hassle free. Also check to see that your passport is valid for at least six months from your return date.
What should I wear on my Chesapeake Bay holiday?
Do some research into the types of clothing people in Chesapeake Bay wear, and consider browsing style blogs for some fashion tips. Aim to create a versatile travel wardrobe full of pieces that suit your destination and showcase your unique style. It’s also a smart move to check the weather forecast so you can pack the right clothes. July is the warmest month in Chesapeake Bay, with average temperatures of 25ºC. January is when much of this destination is at its coolest, so get packing for daily temperatures of around 1ºC.
What does an Expedia Chesapeake Bay holiday include?
Select from a combination of hotels, hire cars and flights. Once you’ve made your booking, add some experiences and tours. Want to pick your airfare class? That’s easy to do too. The choice is all yours when it comes to creating your dream Chesapeake Bay getaway. Expedia has a wide selection of properties in Chesapeake Bay, giving you the freedom to customise your escape. Private holiday homes and apartments are two of the most in-demand options for visitors here.
Does Expedia offer Book Now, Pay Later Chesapeake Bay holidays?
We do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply choose the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Remember to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna’s manageable instalment plans. If paying over multiple transactions sounds right for you, pick this option during the checkout process.
  • No-deposit holidays: Hitting the “book now” button is easier with this payment plan. With no upfront fee for your escape, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Chesapeake Bay Expedia holiday?
Yes — and it’s easy too. Expedia has access to more than 400 partner airlines around the world. Our holiday packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

Discover the most popular places to visit in Chesapeake Bay

Unmissable things to do in Chesapeake Bay

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.