Old Town Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
Price was CA $1,308, price is now CA $946 per person
CA $946
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Washington (DCA)
8.2/10 Very Good! (1,004 reviews)
It was so nice, and it is a college campus, so it is really safe. Pet-friendly and good breakfast. Parking is way too expensive. No need to charge $50 a night when there is plenty of parking.

Reviewed on Apr 4, 2026

Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Price was CA $2,462, price is now CA $1,509 per person
CA $1,509
per person
Jul 1 - Jul 6
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
Everything was amazing the only issue I had was Expedia over booked. Karen was such a help on the matter. She was friendly, patient, & accommodating. She helped to make my trip amazing so grateful for her!

Reviewed on Apr 16, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $3,973, price is now CA $2,590 per person
CA $2,590
per person
Jul 1 - Jul 8
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
Clean facilities and amazing staff

Reviewed on Apr 15, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $2,727, price is now CA $1,778 per person
CA $1,778
per person
Jul 1 - Jul 8
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (743 reviews)
Front staff very helpful but electric keys de-magnetized often

Reviewed on Apr 19, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was CA $4,092, price is now CA $2,853 per person
CA $2,853
per person
Jul 1 - Jul 6
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,417 reviews)
Really classy hotel with wonderful bar and restaurant. Felt like you were in the middle of all there is to see in the city. Loved it!

Reviewed on Apr 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
The price is CA $179 per night from May 3 to May 4
CA $179
CA $202 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
Historic hotel in a historic town. Be sure and check out the Museum of Shenandoah Valley History and Gardens.

Reviewed on Apr 19, 2026

The George Washington Hotel, A Wyndham Grand Hotel
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 $117 per night from Apr 22 to Apr 23
CA $117
CA $128 total
Apr 22 - Apr 23
includes taxes & fees
9.2/10 Wonderful! (1,450 reviews)
Very nice, clean, and modern. Beds were made each day, with new towels. Breakfast is decent, but wish they had real half & half for coffee.

Reviewed on Apr 20, 2026

Microtel Inn & Suites by Wyndham Winchester
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 $150 per night from Apr 22 to Apr 23
CA $150
CA $164 total
Apr 22 - Apr 23
includes taxes & fees
La Quinta Inn & Suites by Wyndham Winchester
See all 382 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Old Town Winchester vacation package cost?
Our Old Town Winchester vacation packages, which begin from just CA $946, 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 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.