Annapolis Holidays

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Top hotels in Annapolis

Timber Cove Resort

Timber Cove Resort

2.5 out of 5
21780 CA-1, Jenner, CA
Fully refundableReserve now, pay when you stay
The price is €387 per night from 15 Sept to 16 Sept
€387
15 Sept - 16 Sept
includes taxes & fees
9.2/10 Wonderful! (264 reviews)
"Excellent dinner! Cozy lounge. Great stay!"

Reviewed on 13 Aug 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
8.8/10 Excellent! (970 reviews)
"Good place near the ocean. We have a big clean room with ocean view. Pizzeria near by is very good."

Reviewed on 12 Aug 2025

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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
7.8/10 Good! (633 reviews)
"Stay was fine, staff was nice and helpful. Walking distances to downtown but, walking there was not pleasant. Seeing dirty clothes on the way made me feel like we were in the bad part of town."

Reviewed on 10 Aug 2025

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Cloverdale Wine Country Inn & Suites
See all 883 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.

Popular places to visit

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

€43
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Kayaking at the Coast!

Russian River Kayak Tour at the Beautiful Sonoma Coast

€117
per adult
100% of travellers recommend
Russian River Kayak Tour at the Beautiful Sonoma Coast
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

€120
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis holiday package cost?
You'll find cheap prices 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 holiday to Annapolis costs.
What are the cheapest months to go to Annapolis?
If you'd like to score a cheap Annapolis holiday package, consider planning a trip in January, February and November. You'll generally find better prices on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Annapolis?
The ideal duration for your Annapolis holiday depends on what you'd like to do. Typically, a few days to a week will give you time to check out all the top attractions and explore some hidden gems 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 holiday package well in advance.
Is it cheaper to book an Annapolis holiday as a package?
Expedia holiday 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 personalised Annapolis holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 holiday.
How to plan a trip to Annapolis?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Annapolis.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your accommodation will probably be the biggest expense during your trip to Annapolis.
  3. Decide how long to go away for: Now that you're up to speed on Annapolis, you can work out the ideal length of your holiday. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, book the right Annapolis holiday package for you.

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