Winchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Winchester Vacation
History, cuisine, art and more … There's so much to discover with a Winchester vacation package. And with the ability to customize your city break, it's guaranteed to be one you won't forget. Eager to start exploring your surroundings? Fair Hill State Natural Resources Management Area, Patriots Glen Golf Club and East Meadow Park are among the leading places to visit during your trip to Winchester. Your dream Winchester vacation is a couple of clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored to suit your style.
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Hive
Northwest
Price was CA $1,237, price is now CA $868 per person
CA $868
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,445 reviews)
Small and efficient rooms. Great location. Helpful, friendly staff. Perfect for my visit.
Reviewed on May 30, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,970, price is now CA $1,211 per person
CA $1,211
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,192 reviews)
Location was ideal. Staff and service were top notch. Will return for sure.
Reviewed on May 31, 2026
The River Inn
Northwest
Price was CA $1,321, price is now CA $952 per person
CA $952
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,954 reviews)
We really enjoyed our stay at this hotel. The rooms were spacious and well-equipped with kitchen appliances, which made our stay very comfortable. What I loved most was that pets are welcome with no extra fees, which is a huge plus. Everyone on the staff was friendly, welcoming, and helpful throughout our stay. I would definitely come back to this hotel the next time I’m in Washington, DC. Highly recommended!
Reviewed on May 30, 2026
Fairmont Washington, D.C., Georgetown
Northwest
Price was CA $1,881, price is now CA $1,381 per person
CA $1,381
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Great location and very nice lobby and bar area. The rooms are spacious and very clean.
Reviewed on May 28, 2026
Winchester Hotel Deals
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundable
The price is CA $103 per night from Jun 29 to Jun 30
CA $103
CA $114 total
Jun 29 - Jun 30
includes taxes & fees
5.8/10 (1,005 reviews)
"Making the reservation was very difficult for me- I ended up not staying at your facility."
Reviewed on May 30, 2026
Sheraton Suites Wilmington Downtown
422 Delaware Ave Wilmington DE
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Jun 14 to Jun 15
CA $220
CA $242 total
Jun 14 - Jun 15
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"The property was well maintained. The staff friendly. The location was downtown so it was perfect. The only negative was there was no assistance with luggage. None available. In spite of that I would stay again."
Reviewed on May 28, 2026
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Jun 7 to Jun 8
CA $247
CA $277 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (225 reviews)
"La pace súper bien y los niñas mucho más gracias"
Reviewed on May 31, 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.
Discover the most popular places to visit in Winchester
Elkton Indoor Tennis
Catch an event at Elkton Indoor Tennis during your trip to Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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.
