Annapolis Vacations from $440

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The Latest Annapolis vacation packages

Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
Save 100% on your flight
Price was $656, price is now $440 per person
$440
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Oakland (OAK)
8.8/10 Excellent! (1,332 reviews)
Friendly helpful checkin, very clean spotless unit in beautiful setting.

Reviewed on Nov 7, 2025

Meadowood Napa Valley

Meadowood Napa Valley

5 out of 5
Save 100% on your flight
Price was $4,827, price is now $3,271 per person
$3,271
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Oakland (OAK)
9.6/10 Exceptional! (146 reviews)
It was wonderful all around

Reviewed on Sep 1, 2025

Carneros Resort and Spa

Carneros Resort and Spa

5 out of 5
Save 100% on your flight
Price was $1,607, price is now $1,127 per person
$1,127
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Oakland (OAK)
9.2/10 Wonderful! (347 reviews)
It is a beautiful property with magnificent grounds. The staff and dining options are great. Highly recommend.

Reviewed on Aug 25, 2025

Hotel Yountville

Hotel Yountville

4 out of 5
Save 100% on your flight
Price was $1,372, price is now $962 per person
$962
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Oakland (OAK)
9.6/10 Exceptional! (1,007 reviews)
Room was spotless and comfortable

Reviewed on Oct 29, 2025

Luxe, Pool, Spa, Fire Pit, Game Room, Piano Sonoma Pool Retreat by Avantstay

Luxe, Pool, Spa, Fire Pit, Game Room, Piano Sonoma Pool Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $9,357, price is now $6,591 per person
$6,591
per person
Dec 26 - Jan 2
found 20 hours ago
Roundtrip flight included
New Orleans (MSY) to Oakland (OAK)
No reviews
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Discover the most popular places to visit in Annapolis

Finding a great place to spend time on the California coast can be difficult. If you get the chance to visit Salt Point State Park and Gerstle Cove State Marine Reserve you won't be disappointed.

Salt Point State Park

You can take time to visit Salt Point State Park during your travels to Cazadero. Amble around the area's parks or visit its monuments.

Salt Point State Park

Flowers Vineyard and Winery

You can enjoy a tasting or tour at Flowers Vineyard and Winery during your travels to Cazadero. Stroll along the area's seaside, or simply savor its top-notch restaurants.

Flowers Vineyard and Winery

Stump Beach

Why not spend a lazy afternoon at Stump Beach during your trip to Cazadero? Wander the riverfront in this relaxing area.

Stump Beach

What to do in Annapolis

Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

$139
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
Giant Redwoods Tour Including a 4-Course Winery Lunch

Giant Redwoods Tour Including a 5-Course Winery Lunch

$234
per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
Ride

Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

$270
per adult
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
See all activities 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
See all 905 properties in Annapolis
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 $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.