Annapolis Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top hotels in Annapolis

Timber Cove Resort

Timber Cove Resort

4.5 out of 5
21780 CA-1 Jenner CA
Fully refundableReserve now, pay when you stay
The price is €349 per night from 1 Sept to 2 Sept
€349
1 Sept - 2 Sept
includes taxes & fees
Timber Cove Resort
Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116 Guerneville CA
Fully refundableReserve now, pay when you stay
The price is €298 per night from 6 Aug to 7 Aug
€298
6 Aug - 7 Aug
includes taxes & fees
9.2/10 Wonderful! (113 reviews)
"Very peaceful and relaxing. The property is so gorgeous and well maintained. The beds were soft, and the showers had great water pressure, just small things that make a big difference."

Reviewed on 22 Jul 2026

Dawn Ranch
Gualala Country Inn

Gualala Country Inn

2.5 out of 5
47975 Center St Gualala CA
Fully refundableReserve now, pay when you stay
The price is €136 per night from 10 Aug to 11 Aug
€136
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"ELECTRICITY WENT OUT, COULDN’T HAVE HEATER ON THE SAME TIME AS THE MICROWAVE. NEXT MORNING, WENT FOR COFFEE, RETURNED TO ROOM AT 9:30 AM, MAID WAS ALREADY IN ROOM BREAKING IT DOWN AND CLEANING. PRIOR TO LEAVING TO GET COFFEE, WE INFORMED THE FRONT DESK WE WERE NOT CHECKING OUT UNTIL 11 AM. WE BASICALLY ..."

Reviewed on 31 Jul 2026

Gualala Country Inn
See all 912 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.

What to do in Annapolis

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

€44
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Shopping in Healdsburg

History Walking Tour of Healdsburg

€39
per adult
History Walking Tour of Healdsburg
Kayaking at the Coast!

Russian River Kayak Tour at the Beautiful Sonoma Coast

€118
per adult
100% of travellers recommend
Russian River Kayak Tour at the Beautiful Sonoma Coast
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis holiday package cost?
You'll find cheap prices on Expedia for your Annapolis break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Annapolis costs.
What are the cheapest months to go to Annapolis?
If you'd like to score a cheap Annapolis holiday package, consider planning a trip in January, February and November. You'll generally find better prices on hotels and flights during these quieter months — perfect for travellers wishing to save money.
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 time to check out all the top attractions and explore some hidden gems along the way.
How to find the best Annapolis package deals?
Use Expedia's filter tool to find some tempting Annapolis package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Annapolis package deals in the low 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 holiday package well in advance.
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, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still get the flexibility to create a personalised Annapolis holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Annapolis?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Annapolis holiday.
How to plan a trip to Annapolis?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Annapolis.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your accommodation will probably be the biggest 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. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, book the right 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.