Winchester Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Hotel Washington

Hotel Washington

Downtown Washington D.C.
Save 100% on your flight
CA $927
per person
Nov 19 - Nov 22
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (2,502 reviews)
Not only is the hotel beautiful, but it is located in a prime spot. We are at vue and fire clay and both were delicious. The staff was helpful as well.

Reviewed on Oct 11, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.
Save 100% on your flight
CA $1,373
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9/10 Wonderful! (1,265 reviews)
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City
CA $1,083
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
8.2/10 Very good! (1,014 reviews)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.
Save 100% on your flight
CA $1,434
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9/10 Wonderful! (2,093 reviews)
citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

Northwest
CA $1,084
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9.2/10 Wonderful! (166 reviews)
The room was clean, comfortable, and quiet. Love it!

Reviewed on Oct 11, 2026

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
A cityscape with a river, modern buildings, and a bridge.

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
A grand library with multiple floors of bookshelves, ornate railings, and a central aisle.

Downtown Baltimore

1 out of top 10 points of interest in this area

Central business district meets historic charm in this neighborhood, with attractions like the National Aquarium, Maryland Science Center, and Lexington Market. Enjoy diverse dining, nightlife, and easy access to public transportation.

Find hotels in Downtown Baltimore
A narrow alleyway flanked by brick buildings with ivy, leading to a body of water.

Fells Point

Historic waterfront neighborhood with a maritime vibe, Fell's Point boasts a high concentration of pubs and restaurants. Explore diverse architecture, unique shops, and reach it easily via water taxi or a short walk from the Inner Harbor.

Find hotels in Fells Point
A large stately building with a prominent central tower, surrounded by lush green lawns and trees.

Timonium

If you're looking for some top things to see and do in Timonium and surrounding area, you can visit Fire Museum of Maryland and Towson Town Center.

Find hotels in Timonium
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Middle East

Though Middle East might not have many top sights, you can venture to the surrounding area to see attractions like Baltimore Inner Harbor Marina and National Great Blacks in Wax Museum.

Find hotels in Middle East

Winchester Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
CA $104
CA $119 total
Oct 18 - Oct 19
includes taxes & fees
8.4/10 Very good! (4,772 reviews)
"The free shuttle to and from the airport and the train station was so helpful and the driver was awesome! The front desk staff was super helpful as well. The only downside we noticed is that the room was humid and the carpet felt damp. Otherwise it was just what we needed after a long travel ..."

Reviewed on Oct 12, 2026

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Sonesta ES Suites Baltimore BWI Airport

Sonesta ES Suites Baltimore BWI Airport

1160 Winterson Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
CA $127
CA $145 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (1,555 reviews)
"Room was mediocre. Place smelled of weed. Our flight was delayed so we got in late and the guy at the counter was irritated that he had to get up to let us in be ause it was after hours."

Reviewed on Oct 11, 2026

Sonesta ES Suites Baltimore BWI Airport
Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

300 Light Street Baltimore MD
Fully refundableReserve now, pay when you stay
CA $241
CA $283 total
Nov 3 - Nov 4
includes taxes & fees
Hyatt Regency Baltimore Inner Harbor
See all 1,380 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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Custom build your Winchester vacation package from as little as CA $927. 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.

Things to do

Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $143
per traveller
94% of travellers recommend
Two Flight Indoor Skydiving Experience
Grand entrance to the Hard Rock Cafe in Baltimore

Dining at Hard Rock Cafe Baltimore

CA $56
per traveller
Dining at Hard Rock Cafe Baltimore
Baltimore's Historical Sightseeing Tour

Baltimore's Historical Sightseeing Tour

CA $67
per adult
98% of travellers recommend
Baltimore's Historical Sightseeing 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.