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 $4,200 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.
The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Price was CA $855, price is now CA $634 per person
CA $634
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,421 reviews)
Clean and spacious Room

Reviewed on Jun 7, 2026

Hotel AKA Alexandria

Hotel AKA Alexandria

4 out of 5
Old Town North
Price was CA $1,108, price is now CA $797 per person
CA $797
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.6/10 Exceptional! (807 reviews)
Great staff and food!

Reviewed on Jun 9, 2026

The River Inn

The River Inn

4 out of 5
Northwest
Price was CA $995, price is now CA $733 per person
CA $733
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,972 reviews)
Very nice big room with a usable kitchen.

Reviewed on Jun 9, 2026

Capitol Hill Hotel

Capitol Hill Hotel

4 out of 5
Capitol Hill
Price was CA $957, price is now CA $706 per person
CA $706
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,345 reviews)
It had all I needed and so convenient to Capitol Hill.

Reviewed on Jun 8, 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Price was CA $919, price is now CA $684 per person
CA $684
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (2,190 reviews)
Nice little hotel near Union Station with good prices and nice staff. Restaurant is the Dubliner pub with great food

Reviewed on Jun 8, 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 $182 per night from Jul 1 to Jul 2
CA $182
CA $207 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"The physical structure of this hotel would have put it at 5 stars, but it seems like they have a really nice property here, but don't know how to run it like a really nice hotel. First, the idea that a hotel of this caliber has an UNO pizza as their hotel is just strange. Also, the bar is gorgeous ..."

Reviewed on Jun 11, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundable
The price is CA $112 per night from Jun 28 to Jun 29
CA $112
CA $127 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Best hotel Ive stayed in a while. However, breakfast was weak. Only boiled eggs and no waffle maker? No cranberry juice? No yogurt? It was sugary cereal, fruits, bagels, bread and sausage patties."

Reviewed on Jun 11, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Jul 5 to Jul 6
CA $107
CA $118 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (941 reviews)
"Pool was nice. Room was clean. Staff was awesome."

Reviewed on Jun 12, 2026

TRU By Hilton Winchester
See all 367 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 $634, 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

Bright Box Theater

3.9/5 (18 reviews)
Enjoy a show at Bright Box Theater, a storied theater in 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.