Old Town Winchester Holidays
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Price found within the past 48 hours. Click for updated prices.
Hyatt Place Baltimore Inner Harbor
Harbor East
S$1,176
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.4/10 Very good! (2,613 reviews)
Stayed 2 nights for a concert. The staff were incredibly nice and helpful, especially being fully booked and all the fans coming in and out. The room was very spacious, clean, and the bed was very comfortable. I loved how around the sink there was space to put my toiletries/makeup. Great things close by in the area as well and easy to get to places via transit/car. The parking fee is a bit exorbitant, but I get it given the proximity to the harbor, but there were other cheaper options nearby so it wasn't terrible.
Reviewed on 17 Aug, 2026
Rachael's Inner Harbor Boutique Inn
Ridgely's Delight
S$1,130
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.8/10 Excellent! (11 reviews)
We had a great time. Was in town for a baseball game and the location was great. The room was clean and very large. We will most likely be back next time the PHILLIES are in town.
Reviewed on 11 Aug, 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
S$1,075
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
9.2/10 Wonderful! (835 reviews)
Top notch experience in a beautiful setting with nice touches, like warm chocolate chip cookies.
Reviewed on 17 Aug, 2026
Pier 5 Hotel Baltimore
Inner Harbor
S$1,012
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.2/10 Very good! (1,339 reviews)
The facility was clean, but this beautiful hotel needs a facelift! A good facelift. It looks very old and outdated which made it seem dirty, which is unfortunate. It is located in a most beautiful area and houses two very nice restaurants. I really didn't interact with the staff that much, so I can't really speak on that too deeply. I did not like that there were not any DO NOT DISTURB signs. I did ask the night guy about it and asked him my room not be cleaned, to which he replied he would handle it. They came and cleaned anyway, and didn't even leave tissue paper, which I had to ask the night guy for that same night I asked housekeeping not to clean especially because I asked them not to clean, and he had to look very hard to find tissue paper. It looked like he might have borrowed a roll from somewhere. Not a big deal, but it kind of is at the same time. We ended up having to use Kleenex the last morning we were there. Also, the hallways, and elevators were VERY HOT. Would I stay there again-maybe. I now know what other options I have.
Reviewed on 17 Aug, 2026
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
S$177
27 Aug - 28 Aug
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"This is a great stop and a beautiful place. Highly recommended and will stay there again when in the area."
Reviewed on 17 Aug, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
S$112
2 Sept - 3 Sept
includes taxes & fees
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
S$136
23 Aug - 24 Aug
includes taxes & fees
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 an Old Town Winchester holiday package cost?
Our Old Town Winchester holiday packages, which begin from just S$1,000, are the best way to save. All you have to do is choose your preferred hotels, flights and rental car to create your perfect getaway.
How do I get a cheap travel package to Old Town Winchester?
Our Old Town Winchester holiday packages offer plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into a handy package. But low prices are only the start of your next epic adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotels around the world to pick from. Whatever your budget or style, there's a package that's perfect for you.
Where should I stay in Old Town Winchester?
A holiday in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Centre and Museum of the Shenandoah Valley. Spend your evenings near these tourist attractions and make sightseeing a breeze.
What are the top hotels in Old Town Winchester?
Whether you plan to stay for a night or a week in Old Town Winchester, you'll get a wonderful night's rest at The George Washington Hotel, A Wyndham Grand Hotel. This option is a favourite with lots of travellers.
How far in advance should I book my Old Town Winchester holiday?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester holiday nice and early. Airlines typically advertise tickets anywhere up to 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Old Town Winchester travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you'll have to do is decide on your favourite combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to craft an amazing Old Town Winchester getaway.
What should I know before booking an Old Town Winchester travel package?
We already have low prices. However, you'll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with an Old Town Winchester Expedia holiday package?
With a holiday package, you're in charge. Whether you're looking to fly to Old Town Winchester in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Old Town Winchester holiday package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We're here to help you every step of the way.
Stay near popular Old Town Winchester attractions
Shenandoah Valley Discovery Museum
8.6/10 (78 reviews)
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Bright Box Theater
7.8/10 (18 reviews)
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Handley Regional Library
9.6/10 (4 reviews)
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
George Washington's Office
8.0/10 (1 review)
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Old Court House Civil War Museum
8.0/10 (1 review)
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
* 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.