Annapolis Vacation Packages

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Top Annapolis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
per person
Aug 29 - Sep 1
found 16 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,010 reviews)
The staff was remarkable. Best service in an American hotel in 20 years. Pool area relaxing and wonderful. Mens locker area with jacuzzi, steam and sauna - top notch.

Reviewed on Jul. 25, 2025

Silverado Resort

Silverado Resort

4 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,008 reviews)
Fabulous property and location. We would stay here again. They do allow pets in some areas and we happened to get a unit by a barky dog.

Reviewed on Jul. 29, 2025

River Terrace Inn - A Noble House Hotel

River Terrace Inn - A Noble House Hotel

4 out of 5
Downtown Napa
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
9/10 Wonderful! (1,002 reviews)
A great location and perfect for walking into town for dinner. Easy parking.

Reviewed on Jul. 30, 2025

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.6/10 Excellent! (1,266 reviews)
Deck dirty, outdoor furniture was dirty, cobwebs around deck, broken blinds on door, door locked but was damaged.

Reviewed on Jul. 29, 2025

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.4/10 Very Good! (1,001 reviews)
Beautiful property. Spacious and clean.

Reviewed on Jul. 28, 2025

Ready to book your vacation to Annapolis?

 

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Annapolis Hotel Deals

Timber Cove Resort

Timber Cove Resort

2.5 out of 5
21780 CA-1, Jenner, CA
The price is CA $371 per night from Aug 24 to Aug 25
CA $371
CA $471 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (260 reviews)
"Nice place"

Reviewed on Jul. 29, 2025

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
The price is CA $194 per night from Aug 3 to Aug 4
CA $194
CA $215 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (959 reviews)
"Property is nice"

Reviewed on Jul. 28, 2025

Gualala Country Inn
Cloverdale Wine Country Inn & Suites

Cloverdale Wine Country Inn & Suites

2.5 out of 5
324 S Cloverdale Blvd, Cloverdale, CA
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 3 to Aug 4
CA $134
CA $150 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (630 reviews)
Good overall stay
"Check in was great and accommodating. At check in, I requested a 2nd floor room away from the highway and road and they were able to fulfill that request. Air conditioning worked very well. My only complaint is the bed was very hard and the pillows were very flat."

Reviewed on Jul. 27, 2025

Cloverdale Wine Country Inn & Suites
See all 892 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.
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Discover the most popular places to visit in Annapolis

Salt Point State Park

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

What to do in Annapolis

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $69
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Giant Redwoods Tour Including a 4-Course Winery Lunch

Giant Redwoods Tour Including a 5-Course Winery Lunch

CA $320
per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
Kayaking at the Coast!

Russian River Kayak Tour at the Beautiful Sonoma Coast

CA $185
per adult
100% of travellers recommend
Russian River Kayak Tour at the Beautiful Sonoma Coast
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
Offering great value package deals from CA $927 on Expedia, you'll be thrilled with how little a vacation to Annapolis costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Annapolis?
January, February and November are great times to search for cheap Annapolis vacation packages. Choosing to travel in quieter months means you can usually find better prices on accommodations and flights.
How many days is enough for Annapolis?
The ideal length for your Annapolis vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Annapolis getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Annapolis?
If you've got your Annapolis travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Annapolis?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Annapolis.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Annapolis.
  3. Decide your trip length: Think about how long you'd like to spend exploring Annapolis. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Annapolis vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.