Winchester-on-the-Severn Holidays

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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 Maryland State House and William Paca 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 NZ$146 per night from 24 Aug to 25 Aug
NZ$146
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (3,857 reviews)
"Our room was clean and the beds were comfortable. We had a nice, hot breakfast (sausage, eggs, waffles,) as well as traditional cold items. Everyone was kind and considerate. We would definitely stay again!"

Reviewed on 13 Aug. 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
815 Elkridge Landing Road, Linthicum Heights, MD
Fully refundable
The price is NZ$227 per night from 31 Aug to 1 Sept
NZ$227
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"I can’t remember the name of the front desk staff member who checked us in, but she was wonderful. I also loved their shrimp tacos, and the shuttle bus drivers were all very friendly. My only complaint was the hot water in the shower, there wasn’t much of it, probably because so many guests were ..."

Reviewed on 13 Aug. 2025

Holiday Inn Baltimore BWI Airport by IHG
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
8.8/10 Excellent! (1,823 reviews)
"Lovely room. Comfortable bed."

Reviewed on 13 Aug. 2025

Get rates
Historic Inns of Annapolis
See all 1,262 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 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

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

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

Activities

Food Tour Plate

Historic Annapolis Food Tour

NZ$134
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

NZ$44
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

NZ$50
per adult
Annapolis Ghosts: Spirits & Spirits 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.