Annapolis Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Annapolis Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Annapolis?
Annapolis Hotel Deals
Dawn Ranch
16467 CA-116 Guerneville CA
Fully refundableReserve now, pay when you stay
CA $395
CA $504 total
Oct 20 - Oct 21
includes taxes & fees
Cottages on River Road
14880 River Rd Guerneville CA
CA $126
CA $152 total
Nov 1 - Nov 2
includes taxes & 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
CA $136
CA $153 total
Nov 10 - Nov 11
includes taxes & 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.
What to do in Annapolis
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
CA $42
per traveller
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $70
per adult
86% of travellers recommend
Frequently asked questions
How much does an Annapolis vacation package cost?
Offering great value package deals from CA $762 on Expedia, you'll be thrilled with how little a vacation to Annapolis costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Annapolis?
January, February and November are great times to search for cheap Annapolis vacation packages. Choosing to travel in quieter months means you can usually find better prices on accommodations and flights.
How many days is enough for Annapolis?
The ideal length for your Annapolis vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Annapolis getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Annapolis?
If you've got your Annapolis travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Annapolis?
- Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Annapolis.
- Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Annapolis.
- Decide your trip length: Think about how long you'd like to spend exploring Annapolis. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Annapolis vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
