Annapolis Vacations from $428
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The Latest Annapolis vacation packages
Price found within the past 48 hours. Click for updated prices.
Calistoga Motor Lodge and Spa
$428
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Oakland (OAK)
8.8/10 Excellent! (477 reviews)
I have been coming to the Motor Lodge for ten years now, and have never been disappointed. The vibe is immaculate - chill, fun, a little like adult summer camp. Love the pools, the restaurant, the beds - it's all carefully planned.
We love coming back year after year.
Reviewed on Aug 26, 2026
Bel Abri Napa Valley Inn
Central Napa
$530
per person
Oct 22 - Oct 25
found 5 hours ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9.6/10 Exceptional! (1,023 reviews)
Such a hidden gem! Rooms were spacious, clean, and had a cozy fireplace. The complimentary breakfast was a delightful perk!
Reviewed on Aug 26, 2026
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
Timber Cove Resort
21780 CA-1 Jenner CA
$384 nightly
$439 total
Sep 20 - Sep 21
Total with taxes and fees
9.2/10 Wonderful! (387 reviews)
"A magical place! The food, the fireplaces, the feelings!"
Reviewed on Aug 26, 2026
Dawn Ranch
16467 CA-116 Guerneville CA
$338 nightly
$386 total
Sep 13 - Sep 14
Total with taxes and fees
9/10 Wonderful! (121 reviews)
"Beautiful location. Very peaceful. Truly enjoyed my stay."
Reviewed on Aug 25, 2026
Gualala Country Inn
47975 Center St Gualala CA
Fully refundableReserve now, pay when you stay
$156 nightly
$174 total
Sep 7 - Sep 8
Total with taxes and 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.
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 $428 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.
