Annapolis Holidays

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    Save up to €900 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

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

Top hotels in Annapolis

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 €70 per night from 1 Sept to 2 Sept
€70
1 Sept - 2 Sept
includes taxes & fees
7.2/10 Good! (347 reviews)
"The room was clean and the staff was friendly and polite. The pool is in disrepair and not usable."

Reviewed on 23 Jul 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 €482 per night from 9 Aug to 10 Aug
€482
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (41 reviews)
"Fun decor. Nice and close to hiking. We had a great time."

Reviewed on 28 Jul 2026

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

The Rustic Retreat

Marshall IN
The price is €235 per night from 3 Sept to 4 Sept
€235
3 Sept - 4 Sept
includes taxes & fees
10/10 Exceptional! (24 reviews)
"An absolutely adorable, clean, luxury house with everything you will need and want. The hot tub was amazing and clean. The grill was fantastic. It has everything you will need in the kitchen. It’s conveniently located. Highly recommend."

Reviewed on 4 Aug 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 holiday package cost?
You'll find cheap prices on Expedia for your Annapolis escape. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Annapolis costs.
What are the cheapest months to go to Annapolis?
If you're looking to book a cheap Annapolis holiday package, consider planning a trip in January, February and November. You'll generally find better rates on flights and accommodation during these quieter months — ideal for a budget-friendly break.
How many days is enough for Annapolis?
With a well-organised itinerary, you can easily hit the main Annapolis sights in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Annapolis holiday for longer.
How to find the best Annapolis package deals?
Start your search for an Annapolis package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Annapolis package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Annapolis getaway off to a flying start.
Is it cheaper to book an Annapolis holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Annapolis holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Annapolis?
If you have your Annapolis travel dates locked in, book as soon as you can to bag some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Annapolis?

  1. Pick your travel dates: The things you'd like to do in Annapolis and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodation will probably be the largest expense during your trip to Annapolis.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Annapolis. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised Annapolis holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.