Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Our guide on where to stay in Winchester
Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
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 Baltimore Inner Harbor Marina or National Aquarium in Baltimore while you're exploring the area.
Downtown Baltimore
1 out of top 10 points of interest in this area
Business and financial trading blend with historical architecture, baseball, live music, museums and theaters in the energetic city center of Baltimore.
Fells Point
The ample dining options and captivating waterfront views are top of the list for many visitors to Fells Point. A stop by Fell's Point Maritime Museum or Vagabond Players might round out your trip.
Timonium
While Timonium isn't home to many top sights, Fire Museum of Maryland and Towson Town Center are some notable places to visit nearby.
Middle East
While Middle East isn't home to many top sights, Baltimore Inner Harbor Marina and National Great Blacks in Wax Museum are some notable places to visit nearby.
Our pick of the best Winchester Hotel Deals
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
NZ$147
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (4,759 reviews)
"The rooms needs to be updated especially the bathrooms. The door was filthy, the water would not drain while in the shower and the toilet makes noise and moves slowly flushing not to mention it smells moldy."
Reviewed on 17 Oct 2026
Lord Baltimore Hotel
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
NZ$256
8 Nov - 9 Nov
includes taxes & fees
Hyatt Regency Baltimore Inner Harbor
300 Light Street Baltimore MD
Fully refundableReserve now, pay when you stay
NZ$351
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very good! (2,026 reviews)
"Very"
Reviewed on 18 Oct 2026
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.
Activities
Two Flight Indoor Skydiving Experience
NZ$178
per traveller
94% of travellers recommend
Baltimore's Historical Sightseeing Tour
NZ$84
per adult
98% of travellers recommend
Glow in the Dark Splatter Paint Experience
NZ$70
per adult
78% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.