Winchester Holidays

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Winchester Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Price was S$2,325, price is now S$2,021 per person
S$2,021
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Baltimore (BWI)
9/10 Wonderful! (2,371 reviews)
not a 4 Star anymore. Wall paper peeling and property looks tired. But staff was great. i will stay again next time/

Reviewed on 2 Jul, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was S$2,502, price is now S$2,089 per person
S$2,089
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
The air-conditioning was very loud. There is no central airflow. The indoor unit is very loud, it is very difficult to sleep next to it. Also we were on the top floor near the elevator, it was very noisy, there was constant noise.

Reviewed on 28 Jun, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was S$2,425, price is now S$2,031 per person
S$2,031
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Baltimore (BWI)
8.2/10 Very good! (2,806 reviews)
Would stay again again. Perfect for my toddler

Reviewed on 3 Jul, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was S$2,566, price is now S$2,150 per person
S$2,150
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Baltimore (BWI)
9/10 Wonderful! (1,199 reviews)
Definitely think this hotel should be labeled 3 or 4 stars instead of 5. How wore down it looks in like the elevators and certain places. Staff super friendly though! Love free the coffee and unique selection of teas but that area was always quite messy and no trash can to throw away items in that area even though I brought it to their attention prior that the trash can was missing.. not sure if its worth 40 dollar a day amenity fee prob wont stay at this location in the future

Reviewed on 1 Jul, 2026

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Price was S$2,429, price is now S$2,105 per person
S$2,105
per person
13 Aug - 18 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Baltimore (BWI)
9.4/10 Exceptional! (1,682 reviews)
Wow!! Amazing stay! Best bed sheets we have ever experienced and the staff is great!! Washington is unbelievable. Thank you for your hospitality.

Reviewed on 3 Jul, 2026

Top hotels in 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 S$117 per night from 27 Jul to 28 Jul
S$117
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun, 2026

Spark by Hilton 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 S$131 per night from 26 Jul to 27 Jul
S$131
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Very inviting front desk lobby. Staff was friendly and courteous. Area by lobby had information on area restaurants, things to do, very helpful."

Reviewed on 2 Jul, 2026

TRU 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 S$138 per night from 19 Jul to 20 Jul
S$138
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"The breakfast was not very good. Save your 10bucks for McDonald's"

Reviewed on 2 Jul, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,108 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 S$2,021 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.