Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Your Winchester Vacation

From its highlights to its hidden delights, this city is best explored with a Winchester vacation package. Check out hotels located in Mount Vernon, which is great for nightlife, dining and culture. Want to get out and explore? National Aquarium in Baltimore, M&T Bank Stadium and Oriole Park at Camden Yards are just three of the best places to visit during your trip to Winchester. A few quick clicks is all it takes to put together a customized Winchester vacation on Expedia.

Top Holiday Package Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
per person
Aug 21 - Aug 26
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
7.8/10 Good! (1,003 reviews)
Service was great. Hotel is beautiful. Good location from PG sports complex

Reviewed on Jun. 29, 2025

Merriweather Lakehouse, Autograph Collection

Merriweather Lakehouse, Autograph Collection

4 out of 5
Town Center
per person
Aug 21 - Aug 26
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (300 reviews)
Nice clean modern hotel , nice friendly staff , convenient location. Easy on site parking

Reviewed on Jun. 29, 2025

Microtel Inn & Suites By Wyndham Rehoboth Beach

Microtel Inn & Suites By Wyndham Rehoboth Beach

2.5 out of 5
Midway
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
9/10 Wonderful! (278 reviews)
Very nice stay close to beach and other activities would definitely go back

Reviewed on Jul. 8, 2025

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

2 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
9/10 Wonderful! (826 reviews)
We will visit again

Reviewed on Jul. 8, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.6/10 Excellent! (1,003 reviews)
Very clean and helpful staff

Reviewed on Jul. 13, 2025

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Top of the World Observation Level showing a city and a bay or harbor

Inner Harbor

2 out of top 10 points of interest in this area

Historic seaport with post-industrial waterfront redevelopment, the Inner Harbor offers attractions like the National Aquarium and Maryland Science Center. Easily walk to stadiums or catch a water taxi to explore nearby areas.

Find hotels in Inner Harbor

Winchester Hotel Deals

Hyatt Regency Baltimore Inner Harbor
Hyatt Regency Baltimore Inner Harbor
4 out of 5
300 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Jul 24 to Jul 25
CA $220
CA $258 total
Jul 24 - Jul 25
includes taxes & fees
8.2/10 Very Good! (1,706 reviews)
Great pool and hotel
"Great stay and great pool for our kids! Very close to Camden Yards, too! Was a perfect stay!"

Reviewed on Jul. 13, 2025

Hyatt Regency Baltimore Inner Harbor
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 CA $109 per night from Jul 20 to Jul 21
CA $109
CA $125 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (3,769 reviews)
"It had a noisy neighbor, but it was not the hotel issue. However, a guard could have a better outcome"

Reviewed on Jul. 12, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
The Royal Sonesta Harbor Court Baltimore
The Royal Sonesta Harbor Court Baltimore
4.5 out of 5
550 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Aug 10 to Aug 11
CA $205
CA $282 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,515 reviews)
front desk staff
"staff was helpful and accommodating. Front desk was very helpful with accessing my bags which I left in car. held our bags and car while we went the ballgame"

Reviewed on Jul. 11, 2025

The Royal Sonesta Harbor Court Baltimore
See all 1,342 properties in Winchester
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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Custom build your Winchester vacation package from as little as CA $833. Pick from any combination of flights, hotels and rental cars to put together the escape you've been dreaming of. Don't forget to add on one or two experiences!
How do I get a cheap travel package to Winchester?
Browse and lock in everything in one place with our Winchester vacation packages. We have incredible bargains on flights, hotels and more that'll keep your credit card happy and your adventurousness alive. And, with more than 550 partner airlines and 1,000,000 hotel options all over the world to choose from, you'll have endless opportunities to mix and match your own way.
Where should I stay in Winchester?
A trip to Winchester isn't complete without stopping by National Aquarium in Baltimore and Oriole Park at Camden Yards. Stay at a hotel within walking distance for quick access to these fantastic attractions.
How far in advance should I book my Winchester vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Winchester sometimes occur a few weeks before departure.
What does an Expedia Winchester travel package include?
Packages include flights, rental cars and hotels, but you can mix and match them to create your dream Winchester vacation. You can also add on tours and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll score deals you won't find elsewhere.
Can I choose my airline with a Winchester Expedia vacation package?
Yes, you sure can. We have more than 550 airline partners across the globe, so go with the carrier that's a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Winchester vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Winchester vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Discover the most popular places to visit in Winchester

Oriole Park at Camden Yards

Oriole Park at Camden Yards

4.5/5(17 reviews)

Watch Baltimore’s beloved baseball team play on their home field, located inside a groundbreaking stadium famous for blending classic and modern design elements.

Oriole Park at Camden Yards
Baltimore Inner Harbor Marina

Baltimore Inner Harbor Marina

4.5/5(15 reviews)

The transformed former seaport is packed with museums, shops and family attractions and is one of the city’s most photographed areas.

Baltimore Inner Harbor Marina
National Aquarium in Baltimore

National Aquarium in Baltimore

4.5/5(21 reviews)

Inner Harbor’s biggest attraction recreates the marine and terrestrial habitats of thousands of animals from many parts of the globe.

National Aquarium in Baltimore

Things to do

Evening view of the roof top deck on the Spirit of Baltimore cruise vessel

Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars

CA $248
per adult
82% of travellers recommend
Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars
Glow in the Dark Splatter Paint Experience

Glow in the Dark Splatter Paint Experience

CA $48
per child
72% of travellers recommend
Glow in the Dark Splatter Paint Experience
Downtown Baltimore Helicopter Tour

Downtown Baltimore Helicopter Tour

CA $172
per adult
Downtown Baltimore Helicopter Tour
See all activities in Baltimore
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.