Annapolis Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Annapolis Vacation

Book a custom vacation package to Annapolis and get ready to experience this fascinating city how you like. Consider spending time in the neighborhood of Historic District, which is good for history and tons more. If a sightseeing tour is part of the program during your trip to Annapolis, stop by leading attractions like U.S. Naval Academy, Maryland State House and William Paca House. Check out Expedia's wide range of travel options and book your ideal vacation to Annapolis now.

Top Annapolis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was CA $877, price is now CA $616 per person
CA $616
per person
Oct 9 - Oct 11
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
The Westin was amazing! This is not the last time we’ll be staying at the hotel!

Reviewed on Aug 2, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,441, price is now CA $1,750 per person
CA $1,750
per person
Sep 9 - Sep 13
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (100 reviews)

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $988, price is now CA $743 per person
CA $743
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,218 reviews)
Other then breakfast everything is perfect For this beautiful hotel must add some good buffet breakfast its suggestions

Reviewed on Aug 2, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,584, price is now CA $1,211 per person
CA $1,211
per person
Oct 13 - Oct 17
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,007 reviews)
I highly recommend. This is a nice hotel, with a affordable luxury vibe. Room lighting, furniture, and layout were great. Very clean. Staff were very helpful and efficient. Fitness room was a little bigger and better equipped than most at this price point. My only minor complaint is that the TV Google Chromecast wouldn't work (I use Chromecast regularly...I think the TV may have been on a different network than the guest wifi). All said, I will likely stay here again for my periodic business travel to this part of DC.

Reviewed on Jul 30, 2026

Unit 3 One BR With Queen Sofa and Bed

Unit 3 One BR With Queen Sofa and Bed

2 out of 5
Downtown Washington D.C.
Price was CA $1,666, price is now CA $1,274 per person
CA $1,274
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (3 reviews)
excellent, beyond expectations.

Reviewed on Jun 15, 2026

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

2 out of top 10 points of interest in this area

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Find hotels in Historic District

Ready to book your vacation to Annapolis?

 

Choose your dates

Annapolis Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Aug 26 to Aug 27
CA $152
CA $221 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (1,906 reviews)
"FACILITY'S NEED IMPROVEMENTS"

Reviewed on Aug 2, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 30 to Aug 31
CA $154
CA $175 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,067 reviews)
"Very affordable and much better than the hotels in the area in this price range. Free parking, good service, comfortable and clean rooms. I will stay here again."

Reviewed on Aug 1, 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is CA $165 per night from Aug 9 to Aug 10
CA $165
CA $189 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Only ice machine in the facility no free coffee not a good selectionof coffee in the rooms. No microwave in roomsprices for snacks way too high in order to eat breakfast you had to pay for it. It should be with the room elevators way to slow on the good side very clean and had a restful night day. ..."

Reviewed on Aug 2, 2026

Crowne Plaza Annapolis by IHG
See all 555 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Annapolis attractions

A grand hall with ornate columns, a large staircase, and flags.

U.S. Naval Academy

9.4/10 (1,474 reviews)
See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.
See properties

What to do in Annapolis

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $14
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $35
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

CA $41
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $616 on Expedia for your Annapolis escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
You can typically find lower rates and greater availability in January, February and March. Browse our cheap Annapolis vacation packages and you could land some great off-season discounts.
How many days is enough for Annapolis?
To get the most out of an Annapolis vacation, we suggest booking for 2 days. Split your time between discovering Annapolis City Dock, Westfield Annapolis Mall and other well-known attractions, as well as experiencing neighbourhoods like Parole and Historic District. If you've got some time to spare, include a day trip or tour in your Annapolis vacation itinerary.
Is it worth booking a vacation package to Annapolis?
Whether you want to visit key attractions such as Annapolis City Dock and Westfield Annapolis Mall on your Annapolis vacation, or coming for its great history, culture and watersports, there's something for everyone here. With so much to see and do, you'll soon find out why so many visitors think Annapolis is a good vacation destination.
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 budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can tailor your Annapolis getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Annapolis?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Annapolis adventure.
How to plan a trip to Annapolis?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Annapolis.
  2. Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Annapolis.
  3. Decide how long to go for: Now that you're up to speed on Annapolis, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Annapolis vacation package.

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