Annapolis Vacations

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Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Timber Cove Resort

Timber Cove Resort

4.5 out of 5
21780 CA-1 Jenner CA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 1,246 per night from Aug 3 to Aug 4
AEDĀ 1,246
AEDĀ 1,590 total
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (364 reviews)
"Itā€™s been our go to about every 5 yrs of 60 living in Ca. This visit, staff was fabulous, food OK, but EVERYTHING overpriced. The avocado toast had barely a hint of avocado. I was charged $5 for a side of avocado, and charged $2 extra for oat milk in my cappuccino. The showerhead gave off a light ..."

Reviewed on 16 July 2026

Timber Cove Resort
Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116 Guerneville CA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 810 per night from Jul 29 to Jul 30
AEDĀ 810
AEDĀ 1,036 total
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (111 reviews)
"The positive: The service was friendly/attentive and when I had requests I mostly felt heard I very much enjoyed my meal at The Lodge I liked that the tipping was included - made life easier I like that there were bikes and kayaks available. Need Improvement: There was literally no place to store ..."

Reviewed on 8 July 2026

Dawn Ranch
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 AEDĀ 499 per night from Jul 21 to Jul 22
AEDĀ 499
AEDĀ 554 total
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"We liked the mini refrigerator, adequate hot water, coffee maker (Kerug), The room was pretty quiet. We didnā€™t care for the steel chairs to sit in as they were not comfortable. We only had one luggage stand and would have liked two. We couldnā€™t figure out how to get movies on the tv, and the directions ..."

Reviewed on 17 July 2026

Gualala Country Inn
See all 912 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.

Frequently asked questions

How much does an Annapolis vacation package cost?
Offering great value package deals 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 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.