Annapolis Vacations from ￥218,673

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Occidental Lodge

The Occidental Lodge

3 out of 5
Price was ￥237,234, price is now ￥218,673 per person
￥218,673
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Oakland (OAK)
8.8/10 Excellent! (707 reviews)
Nice staff, comfortable bed, love the area.

Reviewed on Jul 16, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Price was ￥488,735, price is now ￥394,441 per person
￥394,441
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Oakland (OAK)
9.6/10 Exceptional! (739 reviews)
Hotel checkin was great. I received glass of lineup on check in.And because our room was not ready.We were granted access to the pool area. We received upgraded rooms, which were fabulous.Even larger than the ones we booked with very nice outdoor shower bathtub and fire pit. The staff was very accommodative, and we felt well taken care of.

Reviewed on Jul 16, 2026

Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

4 out of 5
Boyes Hot Springs
Price was ￥336,180, price is now ￥298,228 per person
￥298,228
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Oakland (OAK)
8.8/10 Excellent! (1,003 reviews)
This hotel always delivers. Has quite a bite of activities you can do inside the property, like ping pong, board games, live music and wine tasting. They also can provide you with hiking and other outdoor stuff. The room was good. Bed comfortable and bathroom spacious.

Reviewed on Jul 13, 2026

Geyserville Inn

Geyserville Inn

3.5 out of 5
Price was ￥257,814, price is now ￥240,676 per person
￥240,676
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Oakland (OAK)
9.2/10 Wonderful! (1,002 reviews)
The Grill needs to open earlier for travelers.

Reviewed on Jul 10, 2026

UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

3 out of 5
Price was ￥258,740, price is now ￥241,560 per person
￥241,560
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Oakland (OAK)
9/10 Wonderful! (1,006 reviews)
I had a great stay! The room was clean, comfortable, and well-maintained. The staff was friendly and welcoming, making check-in and check-out easy. The air conditioning worked perfectly, which made the room very comfortable. Parking was convenient, and the overall experience was smooth and enjoyable. I would definitely stay here again and recommend this property to other travelers.

Reviewed on Jul 11, 2026

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 ￥54,983 per night from Aug 3 to Aug 4
￥54,983
￥70,194 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (363 reviews)
"Incredible view! Beautiful stylish rooms with fun stuff like complimentary wine, record player, games, complimentary cookies and coffee, fireplace and fire pit. I especially loved watching the sunset! Food was a bit pricy for the quality. A beautiful place to stay or even visit for a meal."

Reviewed on Jul 14, 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 ￥35,747 per night from Jul 29 to Jul 30
￥35,747
￥45,720 total
Jul 29 - Jul 30
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 Jul 8, 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 ￥22,030 per night from Jul 21 to Jul 22
￥22,030
￥24,454 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"This place is an absolute gem! Would highly recommend."

Reviewed on Jul 15, 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.

What to do in Annapolis

Shopping in Healdsburg

History Walking Tour of Healdsburg

￥7,314
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

￥8,127
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Sonoma Horseback-Riding Tour

Sonoma Horseback-Riding Tour

￥20,968
per adult
100% of travellers recommend
Sonoma Horseback-Riding Tour
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from ￥218,673 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 vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
If you'd like to score a cheap Annapolis vacation 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 travelers wishing to save money.
How many days is enough for Annapolis?
The ideal duration for your Annapolis vacation 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 vacation package well in advance.
Is it cheaper to book an Annapolis vacation as a package?
Expedia vacation 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 personalized Annapolis vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 vacation.
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 accommodations 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 vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the right Annapolis vacation package for you.

Explore a world of travel with Expedia

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