Winchester Vacation Packages
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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.
Malolo Bed and Breakfast
Southeast
Price was CA $1,256, price is now CA $1,019 per person
CA $1,019
per person
May 14 - May 18
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.8/10 Exceptional! (74 reviews)
Jorge and Dave are excellent hosts and shared lots of dining and activity suggestions. We would stay again.
Reviewed on Jun 8, 2025
Placemakr Dupont Circle
Northwest
Price was CA $2,043, price is now CA $1,588 per person
CA $1,588
per person
May 14 - May 18
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.4/10 Very Good! (750 reviews)
I had a great overall experience at this hotel. The room was very comfortable, clean, and well maintained, which made my stay relaxing and enjoyable. Good amenities and atmosphere.
The only downside was the check-in process, which was delayed and took longer than expected.
Overall, I would still recommend this hotel for its comfort and quality for long trips.
Reviewed on Mar 27, 2026
Your DC Comfort Apartments
Groveton
Price was CA $1,570, price is now CA $1,233 per person
CA $1,233
per person
May 14 - May 18
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (4 reviews)
Parking was different but once I figured it out, everything from there was smooth.
Reviewed on Aug 25, 2025
The Hotel at Arundel Preserve
Price was CA $1,481, price is now CA $1,212 per person
CA $1,212
per person
May 26 - May 30
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
9.4/10 Exceptional! (1,704 reviews)
Was nearby for a wedding. Very clean hotel with spacious rooms. The room had a microwave and mini fridge. The on property Mexican restaurant had great margaritas and food! I would definitely stay there again if I was in the area.
Reviewed on Mar 29, 2026
Winchester Hotel Deals
Quality Inn Newark - Wilmington
65 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Apr 20 to Apr 21
CA $92
CA $102 total
Apr 20 - Apr 21
includes taxes & fees
5.6/10 (1,002 reviews)
Raj was very helpful when I was looking for a fork at 11 pm. Refrigerator in the room was not working although it was plugged in.
Reviewed on Apr 1, 2026
Sonesta Select Newark Christiana Mall
48 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from May 3 to May 4
CA $130
CA $144 total
May 3 - May 4
includes taxes & fees
7.6/10 Good! (1,246 reviews)
Location good. Room was not clean, no drain plugs for shower or sink. Breakfast not avail due to hotel changing ownership soon.
Reviewed on Mar 29, 2026
Great Wolf Lodge Perryville
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundableReserve now, pay when you stay
The price is CA $305 per night from Apr 12 to Apr 13
CA $305
CA $341 total
Apr 12 - Apr 13
includes taxes & fees
8.8/10 Excellent! (193 reviews)
Yes great stay
Reviewed on Mar 30, 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.
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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.
