Annapolis Vacations

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Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Gualala Country Inn
Gualala Country Inn
2.5 out of 5
47975 Center St, Gualala, CA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (916 reviews)
"Exceptionally warm check in. Free water, beer at check in. Informational handout for restaurants, local happenings. Incredibly kind and tolerant of families with little ones. Great views too!"

Reviewed on 2025/6/23

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Gualala Country Inn
Timber Cove Resort
Timber Cove Resort
2.5 out of 5
21780 CA-1, Jenner, CA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (248 reviews)
"Loved everything about this resort. I only wish it had been a bit warmer so we could have enjoyed the fire pit overlooking the ocean. Our room was cozy and warmed by a stove fireplace and had a beautiful view of the ocean. We were greeted with delicious cookies and a free glass of wine. More delicious ..."

Reviewed on 2025/6/17

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Timber Cove Resort
Cottages on River Road
Cottages on River Road
2.5 out of 5
14880 River Rd, Guerneville, CA
The price is NT$3,748 per night from Jun 30 to Jul 1
NT$3,748
NT$4,447 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Nice place to enjoy shot stay for vacation. We have few remarks wanted to share with the management team First, our room was for accessible and had may features that were not the right choice for us, second, Hot water was not coming in the bathroom sink and the top shower head in the bathroom, third, ..."

Reviewed on 2025/6/26

Cottages on River Road
See all 889 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'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 vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
If you'd like to score a cheap Annapolis vacation 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 travelers wishing to save money.
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 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 vacation package well in advance.
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, 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 personalized Annapolis vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 vacation.
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 accommodations 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 vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the right Annapolis vacation package for you.

Discover the most popular places to visit in Annapolis

Hauser Bridge

4/5(1 review)

Find out about the history of Cazadero with a stop at Hauser Bridge. Amble around this relaxing area's seaside and enjoy its top-notch restaurants.

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