Annapolis Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Annapolis Holiday

Our pick of the best Annapolis Hotel Deals

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
9.6/10 Exceptional! (75 reviews)
"Right by the black river. Cabin was amazing. It's very secluded. Our host was great! Nice and clean!"

Reviewed on 6 Aug. 2025

Get rates
Rustic River Cabin Getaway
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! (53 reviews)
"We loved the view from overlook cabin. Cabin was clean and cozy. Follow directions property manager sends you because gps will try to take you on a scavenger hunt but this was my fault. Accessing river a sxs or 4x4 definitely needed due to river being up. Very peaceful setting at river and ..."

Reviewed on 5 Jun. 2025

Get rates
Make your reservation fast as inquiries are coming in daily.
Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

Annapolis
The price is NZ$460 per night from 7 Sept to 8 Sept
NZ$460
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (36 reviews)
"It was nice. The only thing it needs is a coffee table."

Reviewed on 13 Jun. 2025

Hillside Cabin #4 Annapolis, MO Black River
See all 113 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 can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday packages, organise 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 holiday 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 holiday package as early as possible.
Is it cheaper to book an Annapolis holiday as a package?
Expedia holiday 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 customised Annapolis holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Annapolis?
If you've got your Annapolis holiday 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 travelling 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 favourite 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 holiday. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodation and airfare: After you've nailed down your dates and duration, lock in the ideal Annapolis holiday package for you.

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