Chesapeake Beach Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Chesapeake Beach Vacation Packages

Chesapeake Beach Hotel Deals

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is SARĀ 637 per night from Aug 2 to Aug 3
SARĀ 637
SARĀ 832 total
2 Aug - 3 Aug
includes taxes & fees
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is SARĀ 357 per night from Jul 29 to Jul 30
SARĀ 357
SARĀ 393 total
29 Jul - 30 Jul
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Todo exelente"

Reviewed on 17 July 2026

St Michaels Inn
Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

2 out of 5
7851 Malcolm Road Clinton MD
Fully refundable
The price is SARĀ 239 per night from Aug 16 to Aug 17
SARĀ 239
SARĀ 270 total
16 Aug - 17 Aug
includes taxes & fees
Econo Lodge Andrews Air Force Base
See all 772 properties in Chesapeake Beach
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.

Stay near popular Chesapeake Beach attractions

A coastal residential area with houses along the beach and a lighthouse in the distance.

Breezy Point Beach

8.4/10 (61 reviews)
Stroll this half-mile Chesapeake Bay shoreline where gentle waves meet fossil-hunting adventures. Relax in shaded picnic areas after swimming in the netted area or trying your luck at the 200-foot fishing pier.
See properties

Frequently asked questions

How much does a Chesapeake Beach vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Chesapeake Beach costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chesapeake Beach?
January, February and April are the best times to look for cheap Chesapeake Beach vacation packages. Traveling in quieter periods means you can usually find lower prices on accommodations and flights.
How to find the best Chesapeake Beach package deals?
Finding a cheap Chesapeake Beach package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chesapeake Beach package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chesapeake Beach vacation as a package?
You can enjoy significant savings on your next Chesapeake Beach break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake Beach?
If you're considering an impromptu Chesapeake Beach trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Chesapeake Beach?

  1. Choose your travel dates: What you'd like to do in Chesapeake Beach and your preferred season can help you decide when to go.
  2. Plan your budget wisely: On top of the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Chesapeake Beach.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Chesapeake Beach. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Chesapeake Beach vacation package for you.