Winchester Holidays from AU$349
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Your Winchester Holiday
Lock in a Winchester holiday package and focus on what matters — enjoying yourself. This means no more planning stresses, just more free time to experience the best of this captivating city, such as its rich history and small-town feel. Want to explore? Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall are a few of the best places to visit during your trip to Winchester. No matter your travel plans or the size of your budget, organising a tailored Winchester holiday is a cinch with Expedia.
The Latest Winchester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Beacon Hotel & Corporate Quarters
Downtown Washington D.C.
Price was AU$440, price is now AU$349 per person
AU$349
per person
5 June - 7 June
found 16 hours ago
Return flight included
Boston (BOS) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
Everything was amazing the only issue I had was Expedia over booked. Karen was such a help on the matter. She was friendly, patient, & accommodating. She helped to make my trip amazing so grateful for her!
Reviewed on 16 Apr 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was AU$4,827, price is now AU$3,533 per person
AU$3,533
per person
10 June - 17 June
found 20 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
9/10 Wonderful! (1,157 reviews)
I think service was the most disappointing at front desk and restaurant . The host Also , we ended up going to Riggs for breakfast one morning because the breakfast menu was very mediocre and eating it for 3 days in a row got very old . Dinner menu is not bad but also only if you eat there once , they don’t even offer daily specials that would add a little variety .
Reviewed on 8 Apr 2026
Arlo Washington DC
Northwest
Price was AU$698, price is now AU$553 per person
AU$553
per person
5 June - 7 June
found 16 hours ago
Return flight included
Boston (BOS) to Baltimore (BWI)
9.4/10 Exceptional! (1,483 reviews)
Hotel was great. Breakfast and morning restaurant service terrible. Consider eating elsewhere if they don’t fix the service of food
Reviewed on 15 Apr 2026
The Melrose Georgetown Hotel
Northwest
Price was AU$609, price is now AU$488 per person
AU$488
per person
5 June - 7 June
found 16 hours ago
Return flight included
Boston (BOS) to Baltimore (BWI)
8.8/10 Excellent! (1,341 reviews)
The stuffs are very friendly and helpful. The gym is great.
Reviewed on 14 Apr 2026
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 27,300 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre |
Our pick of the best Winchester Hotel Deals
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 5 May to 6 May
AU$137
5 May - 6 May
includes taxes & fees
9.2/10 Wonderful! (1,449 reviews)
Very clean property, room. Staff was very friendly. Breakfast wasn’t continental but a big breakfast, complete! Pancakes, eggs, sausage cereal, pastries, fruit! Well worth the price.
Reviewed on 16 Apr 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 13 May to 14 May
AU$206
13 May - 14 May
includes taxes & fees
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
The price is AU$156 per night from 26 Apr to 27 Apr
AU$156
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Very clean & functional room. Bed too soft and lLOUD thrumming noise all night long prevented sufficient sleep.
Reviewed on 13 Apr 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
