Winchester Holidays from AU$2,861

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Your Winchester Holiday

Book a Winchester holiday package and discover the atmosphere and rhythm of this sought-after neighbourhood. With all your travel plans worked out, the only thing you need to concentrate on here is having an absolute ball. Some leading nearby attractions to check out during your trip to Winchester include Oriole Park at Camden Yards, M&T Bank Stadium and Baltimore Museum of Art. Whatever your ideal Winchester holiday looks like, you can turn it into reality with Expedia.

Top Holiday Package Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Pier 5 Hotel Baltimore
Hampton Inn & Suites Baltimore Inner Harbor
Renaissance Baltimore Harborplace Hotel
Ulysses, an Ash Hotel
Baltimore executive Furnished rentals
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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

Our pick of the best Winchester Hotel Deals

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 AU$184 per night from 19 Dec to 20 Dec
AU$184
includes taxes & fees
19 Dec - 20 Dec
8.4/10 Very Good! (2,156 reviews)
"The Waterfront staff was rude. Just because I explained my food allergy."

Reviewed on 24 Nov. 2024

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 AU$175 per night from 17 Dec to 18 Dec
AU$175
includes taxes & fees
17 Dec - 18 Dec
8/10 Very Good! (1,753 reviews)
"The Location was great Whole Foods was down the block which made grocery shopping a breeze and restaurants walking distance. Only 15 min away from the harbor walking it was amazing."

Reviewed on 24 Nov. 2024

Hyatt Place Baltimore Inner Harbor
Holiday Inn Baltimore BWI Airport, an IHG Hotel
Holiday Inn Baltimore BWI Airport, an IHG Hotel
3 out of 5
815 Elkridge Landing Road, Linthicum Heights, MD
Fully refundable
The price is AU$167 per night from 1 Dec to 2 Dec
AU$167
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,000 reviews)
"This was an affordable property to stay at. However, the cost of breakfast and dinner was a bit overpriced and falsely advertised as included on Expedia."

Reviewed on 25 Nov. 2024

Holiday Inn Baltimore BWI Airport, an IHG Hotel
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 AU$2,861. 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.
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.

Discover the most popular places to visit in Winchester

Activities

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