Old Town Winchester Holidays

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Price found within the past 48 hours. Click for updated prices.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was €1,458, price is now €1,045 per person
€1,045
per person
29 May - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9.4/10 Exceptional! (1,675 reviews)
From the second we pulled up to the valet the staff was fantastic. Front desk had everything we needed. Bartender was awesome. Room beautiful. Would definitely book there again.

Reviewed on 25 Apr 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was €2,086, price is now €1,338 per person
€1,338
per person
29 May - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9/10 Wonderful! (1,164 reviews)
Very nice hotel in an excellent location.

Reviewed on 26 Apr 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was €1,765, price is now €1,233 per person
€1,233
per person
29 May - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9/10 Wonderful! (778 reviews)
Great breakfast. Clean room. Great location.

Reviewed on 25 Apr 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was €1,669, price is now €1,205 per person
€1,205
per person
29 May - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
8.8/10 Excellent! (1,007 reviews)
Great staff and a he beds were very comfortable

Reviewed on 21 Apr 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Save 100% on your flight
Price was €2,239, price is now €1,674 per person
€1,674
per person
29 May - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9.4/10 Exceptional! (1,001 reviews)
Convenient walk to restaurants and shopping in Georgetown. Beautiful hotel and large room! The Bar is very cool as well.

Reviewed on 13 Apr 2026

Top hotels in Old Town Winchester

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 €126 per night from 13 May to 14 May
€126
13 May - 14 May
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
Beautiful hotel. They just need to bring the price down a little.

Reviewed on 26 Apr 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 €89 per night from 10 May to 11 May
€89
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Good for an overnight stay on our way up north.

Reviewed on 20 Apr 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 €88 per night from 24 May to 25 May
€88
24 May - 25 May
includes taxes & fees
9.2/10 Wonderful! (1,448 reviews)
Facility is always clean and staff is great

Reviewed on 26 Apr 2026

Microtel Inn & Suites by Wyndham Winchester
See all 380 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.

Frequently asked questions

How much does an Old Town Winchester holiday package cost?
Our Old Town Winchester holiday packages, which begin from just €1,045, 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 holiday 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 holiday in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Centre 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 favourite with lots of travellers.
How far in advance should I book my Old Town Winchester holiday?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester holiday 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 holiday!
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 favourite 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 holiday package?
With a holiday 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 holiday package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester holiday 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.

Things to do

Shenandoah National Park Self-Driving Audio Tour

Shenandoah Tour: Self-Guided Drive

€13
per traveller
96% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.