Annapolis Holidays from NZ$2,553

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The Latest Annapolis Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
per person
24 Jan - 26 Jan
found 12 hours ago
Return direct flight included
Auckland (AKL) to Baltimore (BWI)
9.4/10 Exceptional! (963 reviews)
Property was beautiful. Terrance gave us a wonderful tour and history of the property. Wonderful stay.

Reviewed on 19 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Our guide on where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Annapolis featuring a city and street scenes as well as a small group of people

Historic District

2 out of top 10 points of interest in this area
5/5(2 area reviews)

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotel + flight trips in Historic District

Annapolis Holiday

Our pick of the best 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 NZ$258 per night from 24 Nov to 25 Nov
NZ$258
includes taxes & fees
24 Nov - 25 Nov
8.8/10 Excellent! (1,698 reviews)
"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."

Reviewed on 21 Nov. 2024

Historic Inns of Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$281 per night from 18 Dec to 19 Dec
NZ$281
includes taxes & fees
18 Dec - 19 Dec
9.2/10 Wonderful! (1,001 reviews)
"The staff was the best always checking to see if I needed anything."

Reviewed on 19 Nov. 2024

Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 22 Dec to 23 Dec
NZ$213
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (982 reviews)
"The staff was outstanding; couldn’t have been more helpful. Enjoyed the hotel restaurant several times. Tha room was large and well appointed. The bathroom was good size with a nice walk-in shower."

Reviewed on 11 Nov. 2024

Hilton Garden Inn Annapolis Downtown
See all 554 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?
From just NZ$2,553. Yes, you read that correctly. Our Annapolis holiday packages are a great way to make your budget last longer. Bundle your favourite flights, hotels and rental car and get out and see this fabulous destination.
How do I get a cheap travel package to Annapolis?
Lock in flights that fit in with your schedule, add a hotel room to your booking and see how much you save with an Annapolis holiday package. It’s that simple! From hotels and flights to rental cars and activities, Expedia makes travelling cheap and easy. And with over 550 airlines and 1 000 000 hotel options globally to pick from, you’ll never be short of choice.
Where should I stay in Annapolis?
An escape to Annapolis isn’t complete without spending some time in Historic District, so why not get a hotel in this popular neighbourhood? That way, you’ll be handy to Maryland State House. If U.S. Naval Academy is high on your to-do list, stay in Naval Academy.
What are the top hotels in Annapolis?
Travellers journeying to Annapolis often stay in Historic District. Graduate Annapolis and Historic Inns of Annapolis are well-known options in this neighbourhood. But it’s not the only happening place around town! Eastport is another fantastic area and where you’ll find Crowne Plaza Annapolis, an IHG Hotel and DoubleTree by Hilton Hotel Annapolis.
How far in advance should I book my Annapolis holiday?
While not all air carriers release tickets early, it’s usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you’ll nab some fantastic deals. If you’re booking last minute, there’s a chance you could get lucky. Low prices occasionally become available a few weeks prior to departure.
What does an Expedia Annapolis travel package include?
Flights, rental cars and hotels, or any combination of the three — you decide! Whether you’re venturing to Annapolis on a family road trip or enjoying a solo break, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking an Annapolis travel package?
Our prices are always low. However, you’ll grab even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with an Annapolis Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the perfect carrier to get you to Annapolis will be a cinch.
If I'm not able to travel, can I cancel my Annapolis holiday package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can cancel or change your Annapolis holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Annapolis

U.S. Naval Academy featuring heritage architecture, interior views and military items

U.S. Naval Academy

4/5(3 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.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

5/5(1 review)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge

Anne Arundel Medical Center

If Anne Arundel Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Parole.

Anne Arundel Medical Center

What to do in Annapolis

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

NZ$47
Per adult
Annapolis: Crabtown Boos and Booze Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

NZ$126
Per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

NZ$33
Per adult
Phantoms of Annapolis Ghost Tour By US Ghost Adventures
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.