Anchorage Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Holiday Package Deals in Anchorage

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Baltimore - Inner Harbor by IHG

Staybridge Suites Baltimore - Inner Harbor by IHG

3 out of 5
Downtown Baltimore
per person
Aug 15 - Aug 17
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9/10 Wonderful! (1,000 reviews)
I absolutely loved the history of the building and it’s great location to the Inner Harbor

Reviewed on Jul. 13, 2025

The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Fells Point
per person
Sep 19 - Sep 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (37 reviews)
The property was a lovely and convenient place to stay for a visit to John’s Hopkins.

Reviewed on Jul. 15, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
per person
Aug 15 - Aug 17
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9/10 Wonderful! (1,795 reviews)
Enjoyable. Parking is a hassle.

Reviewed on Jul. 15, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
per person
Sep 19 - Sep 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Room was great for price. Lots of restaurants and close to Towson University.

Reviewed on Jul. 14, 2025

Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
Fells Point
per person
Sep 19 - Sep 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,005 reviews)
Cleanliness of rooms could’ve been better. Beautiful hotel location!

Reviewed on Jul. 15, 2025

Where to stay in Anchorage

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

Historic District

1 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

Anchorage 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 $140 per night from Jul 27 to Jul 28
CA $140
CA $206 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,805 reviews)
"We love our stay here for our son’s USNA I Day."

Reviewed on Jul. 13, 2025

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 CA $213 per night from Aug 3 to Aug 4
CA $213
CA $242 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,012 reviews)
"Great stay! Would come here again."

Reviewed on Jul. 14, 2025

Graduate by Hilton 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 $142 per night from Jul 28 to Jul 29
CA $142
CA $162 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Staff was very nice and professional!"

Reviewed on Jul. 10, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,230 properties in Anchorage
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

Frequently asked questions

How much does an Anchorage vacation package cost?
From as little as CA $317. Yes, you read that correctly. Our Anchorage packages are the easiest way to stretch your budget. Combine your hotels, flights and car rentals and get to know this popular destination.
How do I get a cheap travel package to Anchorage?
Our Anchorage vacation packages offer plenty of savings for the savvy wanderer. For the best deals, simply bundle your hotel, flights and activities into one neat package. But bargain prices are only the start of your next epic adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotel options all over the world to choose from. No matter your budget or style, there's a package here just for you.
Where should I stay in Anchorage?
Most people who travel to Anchorage include both U.S. Naval Academy and Maryland State House on their itineraries. Why not book a hotel that's close to these iconic attractions?
How far in advance should I book my Anchorage vacation?
Your best bet is to book early. Air carriers typically advertise flights nearly 12 months ahead of departure, and this is an ideal opportunity to score some rock-bottom prices. Just been told you need to take some vacation time next month? That's fine too --- Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Anchorage travel package include?
That depends on you. You can pick from a variety of Anchorage packages, such as a hotel, flight and rental car. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your perfect Anchorage trip looks like, you'll save!
What should I know before booking an Anchorage travel package?
You can save a tidy sum by bundling your hotels, airfares and rental cars. Once you've made your booking, you can add on things like tours and activities. Your next unforgettable vacation is only a few clicks away.
Can I choose my airline with an Anchorage Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Simply choose the carrier you want and put together the perfect Anchorage escape.
If I'm not able to travel, can I cancel my Anchorage vacation package?
Yes you can, and we're here to help. You may be able to change or cancel your Anchorage vacation package at no cost within 24 hours of booking. But you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, look up our Customer Service Portal for further information.

Discover the most popular places to visit in Anchorage

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

U.S. Naval Academy

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

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

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

Things to do

Food Tour Plate

Historic Annapolis Food Tour

CA $109
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

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

CA $13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Annapolis: Pirates, Patriots, and Poltergeists of Old Town

CA $49
per adult
Annapolis: Pirates, Patriots, and Poltergeists of Old Town
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.