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.
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Price was CA $923, price is now CA $729 per person
CA $729
per person
May 8 - May 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (2,220 reviews)
Unfortunately, my bathroom was dirty. There was no hand soap, and there was hair everywhere--behind the door, in front of the toilet, in front of the tub, etc. I had already unpacked for a 2 week stay in town, or I'd have moved. The hotel did call and offer to clean for me and to move me. I declined again, I had too much to repack.

Reviewed on Mar 18, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,329, price is now CA $874 per person
CA $874
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
Cleaning staff amazing

Reviewed on Mar 20, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Price was CA $1,497, price is now CA $1,129 per person
CA $1,129
per person
May 8 - May 11
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9.2/10 Wonderful! (157 reviews)
I loved my stay there. The staff was so nice and helpful. I would definitely stay again.

Reviewed on Mar 5, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was CA $1,706, price is now CA $1,295 per person
CA $1,295
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.4/10 Exceptional! (1,427 reviews)
Exceeded expectations!!

Reviewed on Mar 17, 2026

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Price was CA $2,324, price is now CA $1,770 per person
CA $1,770
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.8/10 Exceptional! (1,000 reviews)
Very friendly and professional staff

Reviewed on Mar 18, 2026

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 $168 per night from Apr 12 to Apr 13
CA $168
CA $190 total
Apr 12 - Apr 13
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Location of hotel is great for walking to restaurants and shops.

Reviewed on Mar 18, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
The price is CA $107 per night from Apr 5 to Apr 6
CA $107
CA $121 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service.

Reviewed on Mar 23, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 $147 per night from Mar 26 to Mar 27
CA $147
CA $160 total
Mar 26 - Mar 27
includes taxes & fees
9.2/10 Wonderful! (2,279 reviews)
Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming.

Reviewed on Mar 23, 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 369 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 $729, 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

Jim Barnett Park

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