Annapolis Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 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 hotels in Annapolis
Timber Cove Resort
21780 CA-1 Jenner CA
฿12,188
฿15,431 total
20 Sept - 21 Sept
includes taxes & fees
Casa Secoya
19455 California 116 Monte Rio CA
฿3,953
฿4,514 total
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (634 reviews)
"Enjoyable experience"
Reviewed on 1 Sept 2026
Cottages on River Road
14880 River Rd Guerneville CA
฿3,850
฿4,588 total
30 Sept - 1 Oct
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Clean, comfortable, quiet and fun. We enjoyed the way the place was laid out, the garden like court yard, the lovely breakfast, the s’mores in the evening. It was great! Close to the coast too."
Reviewed on 29 Aug 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: Tasting Pass (Choose 1, 2, or 90 Days)
฿1,291
per adult
Sonoma County Self-Guided Wine Tour: GPS Audio Driving Guide
฿992
per traveller
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?
- 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.
- 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.
- 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.
- 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.
