Annapolis 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*

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    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 Annapolis Vacation Packages

Annapolis Hotel Deals

Royal Inn Rockville IN by Hotel O

Royal Inn Rockville IN by Hotel O

3 out of 5
1659 E US Highway 36 Rockville IN
Fully refundableReserve now, pay when you stay
The price is SARĀ 279 per night from Jul 19 to Jul 20
SARĀ 279
SARĀ 349 total
19 Jul - 20 Jul
includes taxes & fees
7.2/10 Good! (345 reviews)
"Quiet, pleasant easy check-in and out. Room was spacious. Low cost. Set back from the highway in nice rural setting"

Reviewed on 24 June 2026

Royal Inn Rockville IN by Hotel O
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

Marshall IN
The price is SARĀ 1,127 per night from Aug 11 to Aug 12
SARĀ 1,127
SARĀ 2,198 total
11 Aug - 12 Aug
includes taxes & fees
9.4/10 Exceptional! (39 reviews)
"Great space with noted attention to many extra details. Owner has gone above and beyond."

Reviewed on 9 July 2026

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
The Rustic Retreat

The Rustic Retreat

Marshall IN
The price is SARĀ 901 per night from Aug 6 to Aug 7
SARĀ 901
SARĀ 1,048 total
6 Aug - 7 Aug
includes taxes & fees
10/10 Exceptional! (20 reviews)
"Awesome place. Very Clean, well maintained, they thought of all the little details. Highly recommend!"

Reviewed on 13 July 2026

The Rustic Retreat
See all 53 properties in Annapolis
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

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Annapolis costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Annapolis?
If you're hoping to snag a cheap Annapolis vacation package, consider planning a trip in January, February and November. You'll generally find better prices on flights and accommodations during these quieter months ā€” ideal for a budget-friendly getaway.
How to find the best Annapolis package deals?
Use Expedia's filters to help you find some unbeatable Annapolis package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Annapolis package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Annapolis vacation as a package?
You can enjoy significant savings on your next Annapolis getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Annapolis?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Annapolis vacation.
How to plan a trip to Annapolis?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite time of year and the activities available will also help you decide when to escape to Annapolis.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will likely be the largest expense during your trip to Annapolis.
  3. Decide your trip length: Think about how much time you want to spend exploring Annapolis. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose an Annapolis vacation package that brings all your bookings together.