Old Town Winchester Vacation Packages

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Top Holiday Package Deals in Old Town Winchester

Price found within the past 48 hours. Click for updated prices.
The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Price was CA $966, price is now CA $765 per person
CA $765
per person
Dec 17 - Dec 20
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,975 reviews)
The staff was friendly and very helpful. My room was clean. I found the deodorizer that they used throughout the hotel to be overpowering. It was just too much. The other thing that was really strange was that there were constantly large piles of used towels in the hallway outside of my room. That was, frankly, disgusting. I won't go back.

Reviewed on Nov 2, 2026

Harbor free indoor parking

Harbor free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,913, price is now CA $1,390 per person
CA $1,390
per person
Jan 13 - Jan 20
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
No reviews

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,608, price is now CA $1,181 per person
CA $1,181
per person
Jan 13 - Jan 20
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $1,736, price is now CA $1,386 per person
CA $1,386
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Nothing like any Sofitel I knew in other cities and worse than few years ago when I visited here. Bed sheaths were unclean( stain on it!) and even though I took them off, they put them back again. Will not come back here.

Reviewed on Nov 3, 2026

Club Wyndham Old Town Alexandria

Club Wyndham Old Town Alexandria

2.5 out of 5
Old Town Alexandria
Price was CA $1,318, price is now CA $1,062 per person
CA $1,062
per person
Dec 17 - Dec 20
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (50 reviews)

Old Town Winchester Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is CA $182 per night from Nov 19 to Nov 20
CA $182
CA $207 total
Nov 19 - Nov 20
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Dec 1 to Dec 2
CA $98
CA $108 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (1,072 reviews)
"Je remarque que lorsque nous réservons avez Expedia nous avons des chambres médiocres. La salle de bain excessivement petite et très salle. Je ne retournerai plus à cet endroit et je ne réserverai plus avec Expedia"

Reviewed on Nov 3, 2026

Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Nov 8 to Nov 9
CA $115
CA $128 total
Nov 8 - Nov 9
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester
See all 371 properties in Old Town 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.
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Frequently asked questions

How much does an Old Town Winchester vacation package cost?
Our Old Town Winchester vacation packages, which begin from just CA $765, 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 vacation 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 vacation in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Center 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 favorite with lots of travelers.
How far in advance should I book my Old Town Winchester vacation?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester vacation 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 vacation!
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 favorite 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 vacation package?
With a vacation 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 vacation package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester vacation 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 savor the top-notch restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.