Annapolis Vacation Packages

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Top Annapolis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Elm House Inn

Elm House Inn

2.5 out of 5
Central Napa
Price was CA $1,656, price is now CA $1,286 per person
CA $1,286
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9.6/10 Exceptional! (1,638 reviews)
Fabulous staff!

Reviewed on Nov 7, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Price was CA $4,229, price is now CA $3,032 per person
CA $3,032
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9.6/10 Exceptional! (768 reviews)

Napa Valley Marriott Hotel & Spa

Napa Valley Marriott Hotel & Spa

4 out of 5
Linda Vista
Price was CA $1,819, price is now CA $1,333 per person
CA $1,333
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
8.4/10 Very good! (1,006 reviews)

White House Napa - Adults Only

White House Napa - Adults Only

4 out of 5
Napa Abajo
Price was CA $4,401, price is now CA $3,235 per person
CA $3,235
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9.2/10 Wonderful! (660 reviews)

The Estate Yountville

The Estate Yountville

5 out of 5
Price was CA $3,571, price is now CA $2,766 per person
CA $2,766
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9.4/10 Exceptional! (1,000 reviews)

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Annapolis Hotel Deals

Cottages on River Road

Cottages on River Road

2.5 out of 5
14880 River Rd Guerneville CA
The price is CA $128 per night from Dec 1 to Dec 2
CA $128
CA $154 total
Dec 1 - Dec 2
includes taxes & fees
Cottages on River Road
Dawn Ranch

Dawn Ranch

3.5 out of 5
16467 CA-116 Guerneville CA
The price is CA $353 per night from Dec 8 to Dec 9
CA $353
CA $451 total
Dec 8 - Dec 9
includes taxes & fees
9/10 Wonderful! (133 reviews)
"Overall, a pleasant stay at Dawn Ranch. The food at the dining area was good, and the private river access for kayaking was definitely the highlight. Select rooms are pet-friendly. Otherwise, the pet fee is double. Unfortunately, our curtains were broken, and the walls were quite thin so we could ..."

Reviewed on Nov 1, 2026

Dawn Ranch
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 CA $370 per night from Nov 29 to Nov 30
CA $370
CA $487 total
Nov 29 - Nov 30
includes taxes & fees
9.2/10 Wonderful! (406 reviews)
"Lovely site with stunning views from all rooms, and an enjoyable Penisula walk throughout the property. Dinner at the Coast Kitchen was also very nice. Our complaints were that water bottles were not refilled in the rooms, nor were dirty cups & glasses replaced. We ended up going out & buying a jug ..."

Reviewed on Oct 31, 2026

Timber Cove Resort
See all 936 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.
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What to do in Annapolis

Shopping in Healdsburg

History Walking Tour of Healdsburg

CA $64
per adult
History Walking Tour of Healdsburg
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide

Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide

CA $42
per traveller
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $71
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
Offering great value package deals from CA $1,286 on Expedia, you'll be thrilled with how little a vacation to Annapolis costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Annapolis?
January, February and November are great times to search for cheap Annapolis vacation packages. Choosing to travel in quieter months means you can usually find better prices on accommodations and flights.
How many days is enough for Annapolis?
The ideal length for your Annapolis vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Annapolis getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Annapolis?
If you've got your Annapolis travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Annapolis?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Annapolis.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Annapolis.
  3. Decide your trip length: Think about how long you'd like to spend exploring Annapolis. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Annapolis vacation package.

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