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
Beautiful troll downtown Annapolis... #Adventure

Historic District

2 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$133 per night from 22 Feb to 23 Feb
NZ$133
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (4,500 reviews)
The front desk was nice and cordial. The shuttle driver that picked us up from the airport was not pleasant. When he answered the phone the sound annoyed. Unfortunately I had to call him a couple of times and he got really annoyed and bored line rude. The morning driver was definitely friendly and ...

Reviewed on 19 Feb 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 refundable
The price is NZ$156 per night from 23 Feb to 24 Feb
NZ$156
23 Feb - 24 Feb
includes taxes & fees
8.2/10 Very Good! (1,582 reviews)
Perfect

Reviewed on 18 Feb 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 NZ$160 per night from 26 Feb to 27 Feb
NZ$160
26 Feb - 27 Feb
includes taxes & fees
8.2/10 Very Good! (1,241 reviews)
The room an overall hotel was out of date and dirty (peeling paint, etc), with a centipede on the bathroom floor. The pool was also being worked on so we couldn’t use that during our stay. The staff was perfectly friendly etc., the hotel itself just left a ton to be desired.

Reviewed on 19 Feb 2026

SpringHill Suites by Marriott Baltimore BWI Airport
See all 1,295 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

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

NZ$67
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
From haunted harbors to pirate hideouts, the ghosts of Annapolis await.

Ashes and Apparitions of Annapolis Ghost Tour

NZ$54
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Food Tour Plate

Historic Annapolis Food Tour

NZ$133
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.