Old Town Winchester Holidays

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Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was €1,266, price is now €866 per person
€866
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Washington (WAS)
8.8/10 Excellent! (1,830 reviews)
Be aware that random amounts will be taken from your account that the card you use for incidentals is associated with. I was not informed at any time that this would occur and the amounts taken out, three times, had a major impact on my trip as I had budgeted and did not anticipate I would have all these debits that would mean I could not afford to eat and had to skip a planned excursion. I was told the amounts were usually small but again was NEVER told the debits would occur. I have been trying to resolve this for close to a week now with an email having been sent, two voicemail being left but no one has responded to let me know how this would be resolved. The hotel is in a nice part of town, a quick drive to most “tourist” locations, the room was very nice and spacious, the on site restaurant was nice as well but having money taken from your account that has a significant impact on your trip, that you were not told would occur would be the biggest drawback for this hotel along with being informed as to when you’d have the funds returned which hasn’t occurred as of this writing.

Reviewed on 22 Aug 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was €1,675, price is now €1,012 per person
€1,012
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Washington (WAS)
8.6/10 Excellent! (1,006 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on 12 Aug 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was €1,834, price is now €1,133 per person
€1,133
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Washington (WAS)
9.8/10 Exceptional! (39 reviews)
The staff were outstanding and made for a great experience and the room was fabulous! The rooftop bar is beautiful and we had a great time!

Reviewed on 22 Aug 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was €1,917, price is now €1,186 per person
€1,186
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Washington (WAS)
9/10 Wonderful! (1,009 reviews)
Love the stay at the hotel. The breakfast experience could have been better but the food was great. The shower head at the bath tub could improve water pressure. Overall great experience.

Reviewed on 25 Aug 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was €1,332, price is now €872 per person
€872
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful place! Amazing staff!

Reviewed on 21 Aug 2025

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 €114 per night from 31 Aug to 1 Sept
€114
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"An old, historic hotel in excellent condition. The staff was on point, and the rooms were clean and comfortable. Highly recommend."

Reviewed on 22 Aug 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 €95 per night from 1 Sept to 2 Sept
€95
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,132 reviews)
TOO MUCH DOG HAIR
"HATED that disgusting long-haired shaggy gross horse-sized dogs were allowed on the carpets in the hotel. dog hair never comes up when vacumed. two huge hairy dogs were wagging their tails and throwing off long dog hairs all over the rugs by the coffee machines in lobby. i was so grossed out i had ..."

Reviewed on 23 Aug 2025

La Quinta Inn & Suites by Wyndham Winchester
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 €79 per night from 7 Sept to 8 Sept
€79
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Clean and staff was great."

Reviewed on 23 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 357 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 €866, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.