Winchester Holidays

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Top Flight + Hotel Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Price was €2,155, price is now €1,745 per person
€1,745
per person
17 Aug - 23 Aug
found 18 hours ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,902 reviews)
We checked in on July 1st and noticed AC was not cooling. Called the front desk and they said they will send someone to reset and no one came. The temperature outside was 102. By the time they offered to change the room we were already in bed. We said we can change the room next morning. They sent a small table fan. Next morning one Engineer was supposed to come and check and they said they couldn’t get in because of the sign. We have gone out for sightseeing. When we got back room was hot.we complained and we had to move our things three times to three different rooms since some of them had no safe no fridge. Finally we settled for a room without fridge. I request you to refund our first night charges since there was no AC. Hope you understand. Thanks Anand Ramachandran

Reviewed on 11 Jul 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was €2,223, price is now €1,832 per person
€1,832
per person
17 Aug - 23 Aug
found 18 hours ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
The property staff was awesome. Had a problem with TV and never fixed but staff did offer a change of rooms which I did not accept.

Reviewed on 11 Jul 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was €2,388, price is now €2,032 per person
€2,032
per person
17 Aug - 23 Aug
found 18 hours ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
9/10 Wonderful! (1,206 reviews)
Poco confortable

Reviewed on 11 Jul 2026

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was €2,140, price is now €1,833 per person
€1,833
per person
17 Aug - 23 Aug
found 18 hours ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
9.2/10 Wonderful! (1,007 reviews)
Great location and nice spacious room - A/C was out third night with no notification from staff and the water station did not work on our floor.. unacceptable in the extreme heat. Housekeeping did not do a great job.

Reviewed on 9 Jul 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was €2,103, price is now €1,807 per person
€1,807
per person
17 Aug - 23 Aug
found 18 hours ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Everything was great

Reviewed on 11 Jul 2026

Top hotels in 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 €89 per night from 26 Jul to 27 Jul
€89
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,030 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"

Reviewed on 10 Jul 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is €72 per night from 26 Jul to 27 Jul
€72
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on 5 Jul 2026

Spark by Hilton 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 €84 per night from 2 Aug to 3 Aug
€84
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Very clean and nicely decorated property"

Reviewed on 11 Jul 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,120 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.

Stay near popular Winchester attractions

Museum of the Shenandoah Valley

8.8/10 (129 reviews)
Discover the Shenandoah Valley's rich heritage at this cultural cornerstone. Wander through the historic Glen Burnie House and meticulously designed gardens for a refined afternoon of regional exploration.
See properties

Frequently asked questions

How much does a Winchester holiday package cost?
Offering excellent value package deals from €1,745 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.

Explore a world of travel with Expedia

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