Winchester Holidays

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    Save up to NZ$2,400 when you book a flight and hotel together*

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

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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
A cityscape with a river, modern buildings, and a bridge.

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.

Find hotels in Inner Harbor

Our pick of the best Winchester Hotel Deals

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
The price is NZ$196 per night from 16 July to 17 July
NZ$196
16 July - 17 July
includes taxes & fees
Lord Baltimore Hotel
Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4 out of 5
300 Light Street Baltimore MD
The price is NZ$342 per night from 3 Aug to 4 Aug
NZ$342
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very good! (2,035 reviews)
"Good"

Reviewed on 13 July 2026

Hyatt Regency Baltimore Inner Harbor
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
815 Elkridge Landing Road Linthicum Heights MD
Fully refundable
The price is NZ$201 per night from 2 Aug to 3 Aug
NZ$201
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
"I love the dinner and bar services."

Reviewed on 13 July 2026

Holiday Inn Baltimore BWI Airport by IHG
See all 1,374 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.

Activities

Baltimore Orioles Baseball Game at Oriole Park

Baltimore Orioles Baseball Game at Oriole Park

NZ$38
per adult
Baltimore Orioles Baseball Game at Oriole Park
Picture 3 for Activity Baltimore: Fells Point Walking Foodie and History Tour

Discover Baltimore: Fells Point Culinary Food Tour

NZ$192
per adult
100% of travellers recommend
Discover Baltimore: Fells Point Culinary Food Tour
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

NZ$178
per traveller
94% of travellers recommend
Two Flight Indoor Skydiving Experience
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.