Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp173.195 when you book a flight and hotel together*
  • Find the right fit

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

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 Rp2.531.167 per night from 30 Nov to 1 Dec
Rp2.531.167
Rp2.974.122 total
30 Nov - 1 Dec
includes taxes & fees
8.4/10 Very Good! (2,481 reviews)
Happy hour prices on Friday were great.. $20 for a glass of Meoimi on Saturday was

Reviewed on 23 Nov 2025

Renaissance Baltimore Harborplace Hotel
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 Rp1.119.726 per night from 22 Dec to 23 Dec
Rp1.119.726
Rp1.276.487 total
22 Dec - 23 Dec
includes taxes & fees
8/10 Very Good! (4,257 reviews)
Everything was great!

Reviewed on 25 Nov 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
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 Rp1.587.460 per night from 25 Dec to 26 Dec
Rp1.587.460
Rp1.809.704 total
25 Dec - 26 Dec
includes taxes & fees
9.2/10 Wonderful! (1,101 reviews)
Beautiful clean room.

Reviewed on 24 Nov 2025

Holiday Inn Baltimore BWI Airport by IHG
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

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.