Winchester-on-the-Severn Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Winchester-on-the-Severn

Price found within the past 48 hours. Click for updated prices.
Roomza Inner Harbor at Lord Baltimore

Roomza Inner Harbor at Lord Baltimore

2 out of 5
Downtown Baltimore
per person
Aug. 10 - Aug. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (6 reviews)
Roomza has hands down the best staff of any hotel. They are friendly, helpful, and attentive. An added bonus to my stay was free drinks and local snacks. I'm now addicted to the Berger's cookies and Utz Crab Chips! If having the most up to date bathroom is important to you, then maybe you wouldn't like Roomza as the bathroom tile was a bit outdated, but in my mind that was much outweighed by the cleanliness. The main room area was large and modern. This is my new go-to hotel when I travel to Baltimore.

Reviewed on May 24, 2024

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
per person
Jun. 28 - Jul. 1
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Baltimore (BWI)
9.4/10 Exceptional! (903 reviews)
Perfect in every way!

Reviewed on May 21, 2024

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Jun. 27 - Jul. 1
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8/10 Very Good! (1,006 reviews)
The cookies were a great bonus. Clean room, terrific shower

Reviewed on May 24, 2024

Comfort Inn College Park North

Comfort Inn College Park North

2.5 out of 5
per person
Jun. 27 - Jul. 1
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
7/10 Good! (977 reviews)
The smell in the hotel was an over powering scent to mask bad aromas I presume. The area is a little rough and a lot of people hanging around outside and it seems some people are living in the hotel since school buses pick up and drop off kids. Very noisy with thin walls and overall a bit run down. Breakfast was not served in the normal breakfast area, but a small room a very little offering and not well stocked and rather pleasant to even eat anything.

Reviewed on May 22, 2024

Metro Points Hotel

Metro Points Hotel

3 out of 5
per person
Jun. 27 - Jul. 1
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
7/10 Good! (676 reviews)
Everything was awesome

Reviewed on May 21, 2024

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

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 hotel + flight trips in Historic District

Winchester-on-the-Severn Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
2.5 out of 5
1734 W Nursery Rd, Linthicum Heights, MD
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from May 27 to May 28
CA $117
CA $133 total
includes taxes & fees
May 27 - May 28
8/10 Very Good! (2,630 reviews)
"Very busy weekend. Hotel was great. Nice breakfast!"

Reviewed on May 22, 2024

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Motel 6 Laurel, DC - Washington Northeast
Motel 6 Laurel, DC - Washington Northeast
2 out of 5
3510 Old Annapolis Rd, Laurel, MD
Fully refundable
The price is CA $82 per night from May 30 to May 31
CA $82
CA $93 total
includes taxes & fees
May 30 - May 31
7.2/10 Good! (1,005 reviews)
"Great"

Reviewed on May 22, 2024

Motel 6 Laurel, DC - Washington Northeast
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 $214 per night from Jun. 9 to Jun. 10
CA $214
CA $275 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (1,609 reviews)
"Beautiful, central location, well appointed! Heating/cooling system is way loud."

Reviewed on May 21, 2024

Historic Inns of Annapolis
See all 1,188 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester-on-the-Severn vacation package cost?
Our Winchester-on-the-Severn packages, which start at just CA $645, 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

Image for U.S. Naval Academy

U.S. Naval Academy

4.5/5(8 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
Image for 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
Image for Chesapeake Bay Bridge

Chesapeake Bay Bridge

4.5/5(2 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

Other vacations you might like

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