Annapolis Holidays from AU$669
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- Plan, book, travel with confidence
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The Latest Annapolis Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Oakland Downtown-City Center
Downtown Oakland
AU$669
per person
2 Nov - 4 Nov
found 1 day ago
Return direct flight included
Dallas (DFW) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
The front desk staff were super nice and helpful. My friend and I arrived to the hotel SUPER early and they helped us get an early check in. The rooms were nice and clean. It's also a five minute walk from the BART trains.
Reviewed on 7 Sept 2026
Hampton Inn & Suites Oakland Airport-Alameda
Bay Farm Island
AU$778
per person
2 Nov - 4 Nov
found 1 day ago
Return direct flight included
Dallas (DFW) to Oakland (OAK)
8.8/10 Excellent! (1,013 reviews)
My experience was amazing! The hotel is clean, beds comfortable, rooms quiet, delicious breakfast options, and the $10 shuttle service (for both airport pickup/drop off) was great and easy to request.
I would definitely stay there again! Thank you for a great experience!
Reviewed on 6 Sept 2026
Annapolis Holiday
Annapolis Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 13ºC |
Max Temp Summer | 27ºC |
Top Sights | Gerstle Cove, Hauser Bridge and Kruse Rhododendron State Natural Reserve |
Our pick of the best Annapolis Hotel Deals
Timber Cove Resort
21780 CA-1 Jenner CA
Fully refundableReserve now, pay when you stay
AU$593
24 Sept - 25 Sept
includes taxes & fees
9.2/10 Wonderful! (391 reviews)
"The most beautiful and inviting hotel. Staff was great especially at the front desk. The views are just breathtaking."
Reviewed on 1 Sept 2026
Cottages on River Road
14880 River Rd Guerneville CA
AU$136
5 Oct - 6 Oct
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Booked last minute but are glad we found this wonderful place"
Reviewed on 4 Sept 2026
Gualala Country Inn
47975 Center St Gualala CA
Fully refundableReserve now, pay when you stay
AU$217
9 Sept - 10 Sept
includes taxes & fees
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
AU$42
per traveller
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
AU$70
per adult
86% of travellers recommend
Frequently asked questions
How much does an Annapolis holiday package cost?
You'll find cheap prices from AU$669 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.
