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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
Oct 10 - Oct 13
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on Jul. 21, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
10/10 Exceptional! (12 reviews)
Staff extremely friendly and welcoming Rooms very clean

Reviewed on Jul. 16, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
per person
Sep 3 - Sep 10
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,009 reviews)
The staff were friendly and helpful I love the cleanliness of the property. I want to say a thank-you to Ahmet at the front desk.

Reviewed on Jul. 22, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8/10 Very Good! (848 reviews)
Me and my guest enjoyed our stay we will definitely be booking again. 🙃

Reviewed on Jul. 21, 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,550 reviews)
Quick check in after a long flight. Clean room with all the amenities you’ll need after unwinding. Right in the center of restaurants and sites

Reviewed on Jul. 21, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 31 to Aug 1
CA $173
CA $196 total
Jul 31 - Aug 1
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Hotel was very nice. Service was good and it was clean and convenient."

Reviewed on Jul. 14, 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 27 to Jul 28
CA $159
CA $172 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (2,084 reviews)
"The breakfast was nice, and though the property was smaller than I've seen elsewhere, it was very up-to-date and not a 70s or 80s style. Nice design overall."

Reviewed on Jul. 22, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 $94 per night from Jul 23 to Jul 24
CA $94
CA $103 total
Jul 23 - Jul 24
includes taxes & fees
8.4/10 Very Good! (1,093 reviews)
"This was a perfect one night stop on my road trip. The room was large and clean. However, I think the cleaner they use for the floor leaves a residue. I dared to walk on it barefoot and it was a tad slippery, so I recommend wearing slippers. It was quiet and pet friendly! There is a $15 pet fee."

Reviewed on Jul. 21, 2025

Travelodge by Wyndham Winchester
See all 351 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 $731, 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.

Discover the most popular places to visit in Old Town Winchester

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

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