Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to Rp173.195 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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    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
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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

Renaissance Baltimore Harborplace Hotel
Renaissance Baltimore Harborplace Hotel
4 out of 5
202 E Pratt St, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is Rp2.480.045 per night from 29 Jun to 30 Jun
Rp2.480.045
Rp2.914.053 total
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (2,234 reviews)
"I loved everything about the whole experience. The check in was so fast. The desk clerk was very polite and answered all me questions. The check out was done in 30 seconds.."

Reviewed on 24 Jun 2025

Renaissance Baltimore Harborplace Hotel
Hyatt Place Baltimore Inner Harbor
Hyatt Place Baltimore Inner Harbor
3.5 out of 5
511 S Central Ave, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is Rp1.745.730 per night from 17 Jul to 18 Jul
Rp1.745.730
Rp2.051.233 total
17 Jul - 18 Jul
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
"My stay was amazing, staff was friendly and very helpful. My only issues were that it wasn't communicated about the reservation for pool time and on my last day, there was no hot water due to some issue with the city."

Reviewed on 23 Jun 2025

Hyatt Place Baltimore Inner Harbor
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 Rp2.428.700 per night from 29 Jun to 30 Jun
Rp2.428.700
Rp2.853.722 total
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,707 reviews)
"I stay there when I do BWC race. Convenient to everything and the staff are friendly and helpful."

Reviewed on 25 Jun 2025

Hyatt Regency Baltimore Inner Harbor
See all 1,351 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

Towson University

Enjoy the student vibe when you visit Towson University during your trip to Towson. Stroll along the waterfront or experience the entertainment choices in this vibrant area.

Towson University

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

Rp2.031.011
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

Rp569.275
per child
72% of travellers recommend
Glow in the Dark Splatter Paint Experience
Downtown Baltimore Helicopter Tour

Downtown Baltimore Helicopter Tour

Rp2.033.125
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.