Annapolis Vacations from $1,061

Book a Hotel + Flight or Car together to unlock savings

The Latest Annapolis vacation packages

Price found within the past 48 hours. Click for updated prices.
Wydown Hotel
Silverado Resort
MacArthur Place Hotel & Spa
Solage, Auberge Collection
Fairmont Sonoma Mission Inn & Spa
Don't see what you're looking for?
See all available trips from Columbus to Annapolis
View all trips

Discover the most popular places to visit in Annapolis

What to do in Annapolis

Annapolis Hotel Deals

Timber Cove Resort

Timber Cove Resort

2.5 out of 5
21780 CA-1 Jenner CA
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $365 total per night from Feb 3 to Feb 4
$365 total
Feb 3 - Feb 4
Total with taxes and fees
9.2/10 Wonderful! (319 reviews)
Romantic

Reviewed on Jan 23, 2026

Timber Cove Resort
Gualala Country Inn

Gualala Country Inn

2.5 out of 5
47975 Center St Gualala CA
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $139 total per night from Feb 25 to Feb 26
$139 total
Feb 25 - Feb 26
Total with taxes and fees
9/10 Wonderful! (999 reviews)
Very nice and clean room! Very cozy

Reviewed on Jan 26, 2026

Gualala Country Inn
Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116 Guerneville CA
$309 nightly
The price is $353 total per night from Mar 4 to Mar 5
$353 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (92 reviews)
This property would be exceptional if it added additional touches such as robes, slippers, working fireplaces, and retouched rooms. Walls and doors were scuffed throughout, just needed some TLC. Grounds are gorgeous and enjoyed food at restaurant.

Reviewed on Jan 3, 2026

Dawn Ranch
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

More vacations you might like

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from $1,061 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.