Annapolis Vacations

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Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Make your reservation fast as inquiries are coming in daily.
Make your reservation fast as inquiries are coming in daily.
Redford
9.8/10 Exceptional! (51 reviews)
The Best Cabin!
"Pictures on line do not do the cabin justice. It is way nicer in person. View to the river is incredible. We highly recommend renting. I know we will be back. Jeff is a great host who provides any and all information you request. Last minute perfect getaway for Thanksgiving!"

Reviewed on Nov 28, 2024

Get rates
Make your reservation fast as inquiries are coming in daily.
Completely Renovated in May 2023
Completely Renovated in May 2023
Annapolis
The price is ￥17,966 per night from Jun 19 to Jun 20
￥17,966
￥33,010 total
Jun 19 - Jun 20
includes taxes & fees
8.2/10 Very Good! (7 reviews)
Nice little cozy place
"Had a hard time finding, because I forgot to read your instructions. Oops! But found it and was easy to get in. The trains in the evening where intersting to watch do maintenance. We enjoyed a couple new places to eat Thee Abbeys, and Iron Mule. Did Joe's canoe on the black River. Weather ended up ..."

Reviewed on Sep 22, 2024

Completely Renovated in May 2023
New Cabin Just Minutes from Black River
New Cabin Just Minutes from Black River
Annapolis
The price is ￥24,996 per night from Jun 22 to Jun 23
￥24,996
￥43,511 total
Jun 22 - Jun 23
includes taxes & fees
8/10 Very Good! (4 reviews)
Great place to stay
"Was a fantastic place to stay, any questions were answered quickly. Very clean, has everything you need for a weekend, you really only need to pack your clothes and food. We had a issue with the door code on the second day and someone was there to help us within 5 minutes of the call and there was ..."

Reviewed on Apr 13, 2025

New Cabin Just Minutes from Black River
See all 112 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 grab a vacation package to this top destination on Expedia. However, how much your vacation to Annapolis costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Annapolis?
To score cheap Annapolis vacation packages, organize your trip outside of peak times such as school holidays. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Annapolis?
The ideal duration for your Annapolis vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to go to all the major attractions and explore some hidden gems along the way.
How to find the best Annapolis package deals?
Use Expedia's filters to help you find some unbeatable Annapolis package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Annapolis package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book an Annapolis vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Annapolis vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Annapolis?
If you've got your Annapolis vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Annapolis?

  1. Pick your travel dates: The things you plan to do in Annapolis and your favorite season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will probably be the largest expense during your trip to Annapolis.
  3. Decide how long to go away for: Now that you're up to speed on Annapolis, you can work out the ideal length of your vacation. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Annapolis vacation package for you.

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