Winchester Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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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    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

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 S$241 per night from 5 Aug to 6 Aug
S$241
5 Aug - 6 Aug
includes taxes & fees
8.2/10 Very Good! (1,725 reviews)
"This hotel was amazing from start to finish. Service and staff was awesome, amenities were 👍 and we were right in the middle of everything. Walking distance to restaurants and shopping. Super win!!!"

Reviewed on 20 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 S$115 per night from 11 Aug to 12 Aug
S$115
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (3,799 reviews)
"Breakfast offerings were very palatable."

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 S$255 per night from 17 Aug to 18 Aug
S$255
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,546 reviews)
"👍"

Reviewed on 21 Jul, 2025

The Royal Sonesta Harbor Court Baltimore
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.