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 S$496 per night from 9 Jan to 10 Jan
S$496
includes taxes & fees
9 Jan - 10 Jan
9/10 Wonderful! (177 reviews)
"Hotel, restaurant and bar were AWESOME but the family room was really cramped."

Reviewed on 2 Jan,2025

Timber Cove Resort
Jenner Inn
Jenner Inn
3 out of 5
10400 Coast Route 1, Jenner, CA
Fully refundableReserve now, pay when you stay
The price is S$295 per night from 5 Jan to 6 Jan
S$295
includes taxes & fees
5 Jan - 6 Jan
8.6/10 Excellent! (942 reviews)
"Monte Rio Suite. Nice clean, comfortable room with a beautiful view."

Reviewed on 1 Jan,2025

Jenner Inn
Casa Secoya
Casa Secoya
2.5 out of 5
19455 California 116, Monte Rio, CA
Fully refundableReserve now, pay when you stay
The price is S$150 per night from 9 Jan to 10 Jan
S$150
includes taxes & fees
9 Jan - 10 Jan
8.8/10 Excellent! (408 reviews)
"We always stay here because it is easy, clean, cute, and dog friendly! It’s a great option for wine tasting if high end accommodations aren’t your thing or if you have a dog. We have stayed in high end places in Healdsburg but for a quick weekend trip with the dogs - this is our place! During the ..."

Reviewed on 31 Dec,2024

Casa Secoya
See all 931 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 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.

What to do in Annapolis

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

S$68
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

S$317
per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

S$180
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Annapolis

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.