Annapolis Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Annapolis

Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116 Guerneville CA
Fully refundableReserve now, pay when you stay
The price is S$416 per night from 4 Nov to 5 Nov
S$416
4 Nov - 5 Nov
includes taxes & fees
Dawn Ranch
Cottages on River Road

Cottages on River Road

2.5 out of 5
14880 River Rd Guerneville CA
The price is S$138 per night from 1 Nov to 2 Nov
S$138
1 Nov - 2 Nov
includes taxes & fees
9.6/10 Exceptional! (1,014 reviews)
"Everything"

Reviewed on 29 Oct, 2026

Cottages on River Road
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 S$441 per night from 29 Nov to 30 Nov
S$441
29 Nov - 30 Nov
includes taxes & fees
9.2/10 Wonderful! (405 reviews)
"Timber Cove is an exceptional property. The staff is super friendly and helpful. A big thank you to Luna who was so lovely and kind. The grounds are so well kept and the views are truly magical. Definitely dine at Coast Kitchen which offered delicious food in a cozy and inviting setting. Our stay ..."

Reviewed on 14 Oct, 2026

Timber Cove Resort
See all 934 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.

What to do in Annapolis

Shopping in Healdsburg

History Walking Tour of Healdsburg

S$57
per adult
History Walking Tour of Healdsburg
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

S$64
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Private Sailing Tour of Bodega Bay

Private Sailing Tour of Bodega Bay

S$157
per adult
Private Sailing Tour of Bodega Bay
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. 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.