Winchester-on-the-Severn Vacations

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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 which includes 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(83 area reviews)

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.

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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 ₩96,807 per night from Jan 4 to Jan 5
₩96,807
₩110,360 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8/10 Very Good! (4,351 reviews)
Yes the room was clean and comfortable

Reviewed on Dec 21, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
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 ₩107,577 per night from Jan 4 to Jan 5
₩107,577
₩122,638 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.6/10 Excellent! (1,021 reviews)
Overall great experience

Reviewed on Dec 23, 2025

DoubleTree by Hilton Hotel Annapolis
The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
7795 Arundel Mills Blvd Hanover MD
Fully refundableReserve now, pay when you stay
The price is ₩182,586 per night from Jan 1 to Jan 2
₩182,586
₩208,148 total
Jan 1 - Jan 2, 2026
includes taxes & fees
9.4/10 Exceptional! (1,571 reviews)
Thumbs up!

Reviewed on Dec 22, 2025

The Hotel at Arundel Preserve
See all 1,254 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.

Frequently asked questions

How much does a Winchester-on-the-Severn vacation 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?
Vacationers 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 vacation?
Savvy travelers 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 organizing 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 vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our vacation 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 vacation package?
If your vacation 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 which includes military items, interior views and heritage architecture

U.S. Naval Academy

4.5/5(446 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

4/5(270 reviews)

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

Chesapeake Bay Bridge
Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

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