Winchester Holidays

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Top Flight + Hotel Deals in Winchester

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was €622, price is now €622 per person
€622
per person
3 Oct - 10 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Baltimore (BWI)
8.6/10 Excellent! (1,006 reviews)
However, it says that the breakfast included for two people, the staff charged us for all three.

Reviewed on 21 Aug 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

3 out of 5
Price was €794, price is now €665 per person
€665
per person
3 Oct - 10 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Baltimore (BWI)
8/10 Very Good! (3,868 reviews)
Good location very friendly staff good place for stay

Reviewed on 24 Aug 2025

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was €832, price is now €707 per person
€707
per person
3 Oct - 10 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Baltimore (BWI)
8.4/10 Very Good! (1,336 reviews)
Very nice and clean! Unlike the Ramada, which was dirty, bed only had sheets no cover, lamp broken and the env ironment looked like homeless people were being house there. Nothing against the homeless.It should not be on your list of recommendations and I should recieve a refund. Ty

Reviewed on 22 Aug 2025

Motel 6 Odenton, MD - Fort Meade

Motel 6 Odenton, MD - Fort Meade

2 out of 5
Price was €649, price is now €647 per person
€647
per person
6 Oct - 9 Oct
found 6 hours ago
Return direct flight included
Dublin (DUB) to Baltimore (BWI)
5.8/10 (480 reviews)
Our AC was broken upon arrival. The room had spiders in the corners and it just felt dingy and run-down.

Reviewed on 7 Aug 2025

Top hotels in Winchester

Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is €96 per night from 31 Aug to 1 Sept
€96
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,082 reviews)
"I’ve stayed here multiple times in this last time was probably the best. The staff was very helpful and courteous, and the amenities were top-notch."

Reviewed on 18 Aug 2025

Sonesta Select Newark Christiana Mall
DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

4 out of 5
700 N King St, Wilmington, DE
Fully refundableReserve now, pay when you stay
The price is €80 per night from 31 Aug to 1 Sept
€80
31 Aug - 1 Sept
includes taxes & fees
7.2/10 Good! (1,005 reviews)
"It was an easy checkin experience and the room is good for just a 1-3 night stay. Shower water was nice and hot."

Reviewed on 22 Aug 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is €60 per night from 25 Aug to 26 Aug
€60
25 Aug - 26 Aug
includes taxes & fees
5/10 (1,002 reviews)
"There is a door that is tetanus waiting to happen its rusy and my friend cut her hand trying to get to the second floor. But the staff is amazing . The man who checked us in was great. The room was clean however they should get new beds in 242 they are loud and a little uncomfy but for a night or ..."

Reviewed on 21 Aug 2025

Quality Inn Newark - Wilmington
See all 614 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 great value package deals from €622 on Expedia, you'll be pleasantly surprised at how much 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?
You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Winchester holiday packages and you could land some great off-season discounts.
How many days is enough for Winchester?
Usually, a handful of days is enough to tick off the top attractions during your Winchester holiday. However, if you prefer to have more time to rest or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, simply play around with your dates and search again. Bear in mind 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 Winchester break by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winchester?
If you have your Winchester holiday dates confirmed, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Winchester?

  1. Choose your dates: What you plan to do in Winchester and your favourite season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Winchester holiday package.

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