Winchester-on-the-Severn Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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 Winchester-on-the-Severn Holiday

Winchester-on-the-Severn is calling! Whatever type of getaway you have in mind, you can see and experience the best of this neighbourhood with a Winchester-on-the-Severn holiday package. Your trip to Winchester-on-the-Severn wouldn't be complete without seeing leading attractions nearby such as U.S. Naval Academy, Maryland State House and William Paca House. No matter what your ideal Winchester-on-the-Severn holiday looks like, you can make it a reality with Expedia.

Our guide on where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas and neighborhoods for the activities you enjoy most. Learn more about Winchester-on-the-Severn
Annapolis featuring 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
5/5(2 area reviews)

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State House.

Find hotels in Historic District

Our pick of the best Winchester-on-the-Severn Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

3 out of 5
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 16 Feb to 17 Feb
AU$113
16 Feb - 17 Feb
includes taxes & fees
8.2/10 Very Good! (4,435 reviews)
Yes

Reviewed on 16 Jan 2026

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Aloft BWI Baltimore Washington International Airport

Aloft BWI Baltimore Washington International Airport

3 out of 5
1741 W Nursery Road Linthicum Heights MD
Fully refundableReserve now, pay when you stay
The price is AU$129 per night from 25 Jan to 26 Jan
AU$129
25 Jan - 26 Jan
includes taxes & fees
8.2/10 Very Good! (1,519 reviews)
Room was clean and orderly

Reviewed on 12 Jan 2026

Aloft BWI Baltimore Washington International Airport
SpringHill Suites by Marriott Baltimore BWI Airport

SpringHill Suites by Marriott Baltimore BWI Airport

3 out of 5
899 Elkridge Landing Road Linthicum Heights MD
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 26 Jan to 27 Jan
AU$143
26 Jan - 27 Jan
includes taxes & fees
8/10 Very Good! (1,223 reviews)
Room was clean

Reviewed on 11 Jan 2026

SpringHill Suites by Marriott Baltimore BWI Airport
See all 1,278 properties in Winchester-on-the-Severn
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Winchester-on-the-Severn holiday package cost?
Our Winchester-on-the-Severn packages, which start at just , are an awesome way to save. All you have to do is choose your preferred hotels, flights and more to create your perfect getaway.
How do I get a cheap travel package to Winchester-on-the-Severn?
You'll save a ton of money if you combine your flights, car rentals and hotels into a Winchester-on-the-Severn travel package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 partner airlines and 1 000 000 hotels worldwide, so you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Winchester-on-the-Severn?
Holiday Makers come from far and wide to see U.S. Naval Academy and Maryland State House in Winchester-on-the-Severn. Book a room near these awesome attractions to make sightseeing a breeze.
How far in advance should I book my Winchester-on-the-Severn holiday?
Savvy travellers often reserve their seats as early as possible. You can generally compare international fares on Expedia up to 12 months before your intended flight. If you're booking at the last minute, there's no need to worry. Discounted prices occasionally become available just weeks before departure.
What does an Expedia Winchester-on-the-Severn travel package include?
Car rentals, hotels and flights — we connect you to the best deals. All you have to do is select your preferred combination. After you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an amazing Winchester-on-the-Severn getaway.
What should I know before booking a Winchester-on-the-Severn travel package?
When you book your hotels, flights and car rentals together, you'll be rewarded with awesome discounts. Whether you're organising a beach break in a villa or want to stay in an upscale city hotel, Expedia can make it happen for less.
Can I choose my airline with a Winchester-on-the-Severn Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our holiday packages give you the flexibility to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Winchester-on-the-Severn holiday package?
If your holiday plans in Winchester-on-the-Severn have been upended, it's good to know that you can cancel your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a cancellation fee. For more information, check our Customer Service Portal.

Discover the most popular places to visit in Winchester-on-the-Severn

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
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

Activities

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Ashes and Apparitions of Annapolis Ghost Tour

AU$48
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Food Tour Plate

Historic Annapolis Food Tour

AU$120
per adult
Historic Annapolis Food Tour
Ghosts of Annapolis: Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

AU$54
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
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.