Annapolis Vacations from $440

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.
RiverPointe Napa Valley Resort
Meadowood Napa Valley
Carneros Resort and Spa
Hotel Yountville
Luxe, Pool, Spa, Fire Pit, Game Room, Piano Sonoma Pool Retreat by Avantstay
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
$352 nightly
The price is $397 total per night from Dec 11 to Dec 12
$397 total
Dec 11 - Dec 12
Total with taxes and fees
9.2/10 Wonderful! (293 reviews)
Very accommodating with our pet, beautiful location, wonderful restaurant and bar on property

Reviewed on Nov 10, 2025

Timber Cove Resort
Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116, Guerneville, CA
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $325 total per night from Nov 30 to Dec 1
$325 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (87 reviews)
We loved the property, amenities and friendly staff.

Reviewed on Nov 6, 2025

Dawn Ranch
Cottages on River Road

Cottages on River Road

2.5 out of 5
14880 River Rd, Guerneville, CA
$105 nightly
The price is $119 total per night from Nov 19 to Nov 20
$119 total
Nov 19 - Nov 20
Total with taxes and fees
9.4/10 Exceptional! (1,003 reviews)
Staff was friendly, room very clean and parking was right across to the room

Reviewed on Nov 8, 2025

Cottages on River Road
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 $440 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.