Anchorage Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Anchorage

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Catonsville, Md – Baltimore West

Studio 6 Suites Catonsville, Md – Baltimore West

2 out of 5
Price was CA $1,348, price is now CA $977 per person
CA $977
per person
Sep 19 - Sep 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (488 reviews)
Our Bathroom sink would fill up due to slow drainage. Macaroni noodles found on bathroom counter. Cigarette stained sheets. Everything was sticky, remote control, phone. Noisy guests in room next door.

Reviewed on Jul 7, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,096, price is now CA $1,403 per person
CA $1,403
per person
Sep 17 - Sep 21
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (81 reviews)
The staff made the trip feel like I was welcomed and mattered! Absolutely would recommend!

Reviewed on Jul 5, 2026

DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
Price was CA $1,522, price is now CA $1,095 per person
CA $1,095
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,002 reviews)
The poperty was in a great place for traveling. The room was clean and staff were professional. My disappointment was in the room. I guess at some point the air system and they put the floor model air conditioners in the room that vent through the window. That is not an issue with me, is it how it was vent. Just little pieces of duct tape holding it to the window which still allowed the access heat in the room that we had on the 4th floor.

Reviewed on Jul 6, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $2,013, price is now CA $1,456 per person
CA $1,456
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (2,841 reviews)
If you want to stay at an upgraded Motel 6 this is it. Room was not clean! The towels appeared to have been used, a Bobby pin was left on the floor and the pillow cases were stained. It was okay for one night and a roof over my head but that was it.

Reviewed on Jul 7, 2026

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
Arundel Mills
Price was CA $1,741, price is now CA $1,269 per person
CA $1,269
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
9.4/10 Exceptional! (1,848 reviews)
This hotel was super clean and the staff was amazing

Reviewed on Jul 6, 2026

Where to stay in Anchorage

Find the best Anchorage areas and neighborhoods for the activities you enjoy most. Learn more about Anchorage
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

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 $128 per night from Aug 3 to Aug 4
CA $128
CA $195 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,883 reviews)
"Great location to historical areas. Great restaurants within walking distance. Rooms were spacious. Staff were great. Plenty of free parking near hotel. Would absolutely stay here again!!"

Reviewed on Jul 7, 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 $147 per night from Jul 12 to Jul 13
CA $147
CA $167 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
"Clean rooms"

Reviewed on Jul 7, 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 $180 per night from Jul 14 to Jul 15
CA $180
CA $206 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Staff was very nice."

Reviewed on Jul 6, 2026

Crowne Plaza Annapolis by IHG
See all 1,229 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 $977. 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.

Things to do

Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $38
per adult
Ashes and Apparitions of Annapolis Ghost Tour
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
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $113
per adult
Historic Annapolis Food Tour
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.