Annapolis Holidays from AU$527

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The Latest Annapolis Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Oakland Downtown City Center

Ramada by Wyndham Oakland Downtown City Center

2.5 out of 5
Downtown Oakland
per person
18 Sept - 21 Sept
found 21 hours ago
Return direct flight included
Boise (BOI) to Oakland (OAK)
7/10 Good! (1,003 reviews)
Daily breakfast. Clean and comfortable rooms. Friendly and helpful staff. I have no complaints.

Reviewed on 16 Jul. 2025

The Meritage Resort and Spa

The Meritage Resort and Spa

4 out of 5
Soscol Gateway South
Save 100% on your flight
per person
18 Sept - 21 Sept
found 21 hours ago
Return direct flight included
Boise (BOI) to Oakland (OAK)
8/10 Very Good! (1,006 reviews)
Long wait lines to check in didn’t love the customer service

Reviewed on 17 Jul. 2025

Executive Inn & Suites Embarcadero Cove

Executive Inn & Suites Embarcadero Cove

3 out of 5
East Peralta
per person
18 Sept - 21 Sept
found 21 hours ago
Return direct flight included
Boise (BOI) to Oakland (OAK)
8.8/10 Excellent! (1,000 reviews)
Beautiful place and great staff

Reviewed on 14 Jul. 2025

Holiday Inn Express Hotel & Suites Oakland-Airport by IHG

Holiday Inn Express Hotel & Suites Oakland-Airport by IHG

2.5 out of 5
per person
18 Sept - 21 Sept
found 21 hours ago
Return direct flight included
Boise (BOI) to Oakland (OAK)
8.8/10 Excellent! (1,003 reviews)
The hotel was okay but I found the location a bit inconvenient for a first time visit (not the hotel’s fault). It is good for a short visit or transit as it is near the Oakland airport. The breakfast was good and it is considerate that they provide bags to carry food items. They also have coffee 24/7 which is great. However, the staff could have done better in communicating during check-in that they do not clean rooms daily unless guests request. I came back late at night to find an unkempt room that was stinking of my take-out leftovers from the previous day’s dinner that were still in the bin.

Reviewed on 13 Jul. 2025

Sonesta Emeryville - San Francisco Bay Bridge

Sonesta Emeryville - San Francisco Bay Bridge

3 out of 5
per person
18 Sept - 21 Sept
found 21 hours ago
Return direct flight included
Boise (BOI) to Oakland (OAK)
8.6/10 Excellent! (1,123 reviews)
The staff were very helpful, courteous and went out of their way to accommodate my requests. The hotel is very conveniently located and has a mall and shopping within walking distance. Overall we enjoyed our stay here.

Reviewed on 11 Jul. 2025

Annapolis Holiday

Annapolis Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
13ºC
Max Temp Summer
27ºC
Top Sights
Gerstle Cove, Hauser Bridge and Kruse Rhododendron State Natural Reserve

Our pick of the best Annapolis Hotel Deals

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! (938 reviews)
"Clean, friendly, convenient- all as always!! Thank you a lot!"

Reviewed on 15 Jul. 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! (627 reviews)
"Solo q e ido a otros lugares y te disen si ahi desayuno gratis o algo como usar los servisios q tienen como pisina o gipnasio cosas asi y pues no nos dijeron nada"

Reviewed on 14 Jul. 2025

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Cloverdale Wine Country Inn & Suites
Timber Cove Resort

Timber Cove Resort

2.5 out of 5
21780 CA-1, Jenner, CA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (251 reviews)
"If you are looking for a place to relax and recharge this is it."

Reviewed on 13 Jul. 2025

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Timber Cove Resort
See all 891 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

What to do in Annapolis

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

AU$76
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

AU$205
per adult
100% of travellers recommend
Russian River Kayak Tour at the Beautiful Sonoma Coast
Giant Redwoods Tour Including a 4-Course Winery Lunch

Giant Redwoods Tour Including a 5-Course Winery Lunch

AU$358
per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis holiday package cost?
You'll find cheap prices from AU$527 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.