Annapolis Vacations from $713
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The Latest Annapolis vacation packages
Price found within the past 48 hours. Click for updated prices.
What to do in Annapolis
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
$30
per traveler
Russian River Kayak Tour at the Beautiful Sonoma Coast
$135
per adult
100% of travellers recommend
Annapolis Hotel Deals
Dawn Ranch
16467 CA-116 Guerneville CA
Fully refundableReserve now, pay when you stay
$309 nightly
$353 total
Oct 20 - Oct 21
Total with taxes and fees
Cottages on River Road
14880 River Rd Guerneville CA
$94 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
"Boutique style bedding and breakfast. Nice and quiet. Will go back there again."
Reviewed on Oct 11, 2026
Cloverdale Wine Country Inn & Suites
324 S Cloverdale Blvd Cloverdale CA
Fully refundableReserve now, pay when you stay
$96 nightly
$108 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (736 reviews)
"Unfortunately, our stay was very disappointing. We found a cockroach and noticed cockroach traps, which immediately raised concerns about cleanliness and pest control. Although the room appeared reasonably clean at first glance, finding a cockroach was unacceptable. On top of that, several amenities ..."
Reviewed on Oct 12, 2026
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.
Find the Best Annapolis Vacation Packages
Annapolis Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Gerstle Cove, Kruse Rhododendron State Natural Reserve and Hauser Bridge |
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Frequently asked questions
How much does an Annapolis vacation package cost?
You'll find cheap prices from $713 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're hoping to snag a cheap Annapolis vacation package, consider traveling in November, December and January. You'll generally find better rates on hotels and airfares during these months — ideal for a budget-friendly break.
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 visit all the leading attractions and discover some hidden spots 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.
Does Expedia offer Book Now, Pay Later Annapolis vacation packages?
Your Annapolis break is meant to be a relaxing escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
