Winchester Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Flight + Hotel Deals in Winchester

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 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 €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
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 €74 per night from 15 Sept to 16 Sept
€74
15 Sept - 16 Sept
includes taxes & fees
9/10 Wonderful! (1,324 reviews)
Excellent stay
"We had a great overnight stay. Easy and friendly check in/check out, very clean and comfortable room and decent breakfast options. There is ample parking and felt safe. My dog loved the window seat. Will definitely stay here again."

Reviewed on 23 Aug 2025

Microtel 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 1,981 properties in 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 a Winchester holiday package cost?
Offering excellent value package deals from €866 on Expedia, you'll be surprised at how little a holiday to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
If you'd like to score a cheap Winchester holiday package, consider travelling in December, January and February. You're likely to find better prices on flights and accommodation during these months — perfect for travellers wishing to save money.
How many days is enough for Winchester?
Allow around 2 days for your Winchester holiday in order to enjoy everything that makes this place unique. Wander around key areas, including Old Town Winchester and College Park. Then check out major sights like Abram's Delight and Museum of the Shenandoah Valley. With a clever itinerary, you can keep busy with room for some rest time too. Want to go beyond Winchester? Consider fitting in an excursion or two.
Is it worth booking a holiday package to Winchester?
It's easy to see why a Winchester holiday is on the to-do list of many travellers. Top attractions like Shenandoah Valley Discovery Museum are just the start of what you can explore here.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester retreat by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winchester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester trip.
How to plan a trip to Winchester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to holiday in Winchester.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Winchester. Then, pick a property that fits your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Decide how long to go for: Now that you know more about Winchester, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Winchester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.