Upperville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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 Upperville Vacation
When you choose a Upperville vacation package, you can relax and enjoy your getaway to the fullest. Uncover the sights and sounds of this fascinating city knowing that everything has been taken care of in advance. During your trip to Upperville, take all the time you need for sightseeing. A fantastic place to begin is Sky Meadows State Park. Expedia is here to help you escape the everyday. Tailor your vacation to Upperville to match your travel style, whatever that may be.
Top Upperville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
West End Washington DC, Tapestry Collection by Hilton
Downtown Washington D.C.
Price was CA $792, price is now CA $649 per person
CA $649
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
Clean room, friendly staff
Reviewed on Jan 2, 2026
InterContinental Washington D.C. - The Wharf by IHG
Southwest
Price was CA $1,252, price is now CA $726 per person
CA $726
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Everything was excellent!
Reviewed on Jan 25, 2026
AC Hotel by Marriott Washington DC Capitol Hill Navy Yard
Navy Yard
Price was CA $996, price is now CA $778 per person
CA $778
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (627 reviews)
Room was very spacious and clean
Reviewed on Jan 31, 2026
Beacon Hotel & Corporate Quarters
Downtown Washington D.C.
Price was CA $858, price is now CA $689 per person
CA $689
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (DCA)
7.6/10 Good! (1,022 reviews)
The room was comfortable, clean and the staff were friendly.
Reviewed on Feb 6, 2026
Homewood Suites by Hilton Washington, D.C. Downtown
Downtown Washington D.C.
Price was CA $971, price is now CA $818 per person
CA $818
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
Everything was great!
Reviewed on Feb 1, 2026
Upperville Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is CA $806 per night from Mar 1 to Mar 2
CA $806
CA $990 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (378 reviews)
Room was awesome, amazing experiences at the resort and really great customer service
Reviewed on Jan 18, 2026
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza Ashburn VA
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Mar 15 to Mar 16
CA $129
CA $147 total
Mar 15 - Mar 16
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Room with Jacuzzi tub in it was so nice. Everything spotless great stay! Recommended!
Reviewed on Feb 8, 2026
Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,001 reviews)
yes
Reviewed on Feb 3, 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.
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.
