Winchester Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 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

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Default Image

Inner Harbor

2 out of top 10 points of interest in this area

The captivating waterfront views and popular shops are just a few highlights of Inner Harbor. Make a stop by National Aquarium in Baltimore or Baltimore Inner Harbor Marina while you're exploring the area.

Find hotels in Inner Harbor

Top hotels in Winchester

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 ฿5,203 per night from 24 Jul to 25 Jul
฿5,203
฿6,114 total
24 Jul - 25 Jul
includes taxes & fees
8.2/10 Very Good! (1,714 reviews)
"The front desk and the Bistro service was excellent. The one problem I had was that my room was not serviced. I went the the front desk to ask why and they showed that it was. I said I left the room around 10:00am and the”do not disturb “ sign was not on the outside of the door. I made the bed myself ..."

Reviewed on 19 Jul 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 ฿2,643 per night from 27 Jul to 28 Jul
฿2,643
฿3,013 total
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (3,794 reviews)
Exactly what we needed.
"A Great Stay Close to BWI airport with an available shuttle to and from the airport."

Reviewed on 19 Jul 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 ฿4,697 per night from 17 Aug to 18 Aug
฿4,697
฿6,470 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,532 reviews)
"We loved our room and the location. However, there was not enough staff to accommodate the amount of people checking in. Housekeeping was running behind and we had to wait for towels for a few hours. The pool was nice. Overall nice stay, but very dated look and feel."

Reviewed on 19 Jul 2025

The Royal Sonesta Harbor Court Baltimore
See all 1,344 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.

Frequently asked questions

How much does a Winchester holiday package cost?
Custom build your Winchester holiday package from as little as . 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 holiday 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 holiday?
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 holiday. 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.
What should I know before booking a Winchester travel package?
When you book your flights, hotels and car rentals together, you'll enjoy awesome discounts. Whether you're organising a beach escape in a villa or want to stay in a ritzy city hotel, Expedia can help make it happen.
Can I choose my airline with a Winchester Expedia holiday 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 holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Winchester holiday 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.

Popular places to visit

Oriole Park at Camden Yards

Oriole Park at Camden Yards

5/5(4 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
National Aquarium in Baltimore

National Aquarium in Baltimore

4.5/5(7 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
Johns Hopkins Hospital

Johns Hopkins Hospital

5/5(1 review)

If Johns Hopkins Hospital is what brings you to town, hopefully you'll have a chance to explore more of Baltimore.

Johns Hopkins Hospital

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

฿4,324
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

฿1,135
per child
78% of travellers recommend
Glow in the Dark Splatter Paint Experience
Downtown Baltimore Helicopter Tour

Downtown Baltimore Helicopter Tour

฿4,055
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.