Upperville Vacation Packages

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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.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Sep 11 - Sep 13
found 1 hour ago
Roundtrip flight included
Toronto (YTZ) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Love the staff. Love the lobby and my room with exception of the bathrooms. poorly lit and attended. elevators are slow and smell

Reviewed on Aug. 11, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Sep 11 - Sep 13
found 1 hour ago
Roundtrip flight included
Toronto (YTZ) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
The staff there were great, and we loved the room.

Reviewed on Aug. 11, 2025

Fairfield Inn by Marriott Washington D.C.

Fairfield Inn by Marriott Washington D.C.

3 out of 5
Northeast
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.4/10 Very Good! (1,018 reviews)
This is sn excellent location. Near food and highway

Reviewed on Aug. 12, 2025

Holiday Inn Washington Capitol - Natl Mall by IHG

Holiday Inn Washington Capitol - Natl Mall by IHG

3 out of 5
Southwest
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.6/10 Excellent! (2,870 reviews)
We had a nice stay in Washington at this hotel.

Reviewed on Aug. 11, 2025

West End Washington DC, Tapestry Collection by Hilton

West End Washington DC, Tapestry Collection by Hilton

3 out of 5
Downtown Washington D.C.
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.6/10 Excellent! (1,001 reviews)
Good location, metro station nearby,,, very good place.

Reviewed on Aug. 6, 2025

Ready to book your vacation to Upperville?

 

Choose your dates

Upperville Hotel Deals

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from Sep 1 to Sep 2
CA $256
CA $343 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Food service was slow. No hosts."

Reviewed on Aug. 9, 2025

Lansdowne Resort and Spa
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Sep 1 to Sep 2
CA $143
CA $155 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on Aug. 10, 2025

La Quinta Inn & Suites by Wyndham 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 CA $128 per night from Aug 17 to Aug 18
CA $128
CA $144 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Staff was very helpful and accommodating. Thanks so much!"

Reviewed on Aug. 9, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 706 properties in Upperville
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Upperville vacation package cost?
You'll find cheap prices from CA $534 on Expedia for your Upperville break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Upperville costs.
What are the cheapest months to go to Upperville?
The off-season is the best time to travel to Upperville if you're on a budget. Another tip for getting cheap Upperville vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Upperville?
With a well-planned itinerary, you can easily hit the most popular Upperville sights in a few days. But if you want to explore off the beaten track or take day trips, consider booking your Upperville vacation for longer.
How to find the best Upperville package deals?
Landing a cheap Upperville package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Upperville package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Upperville vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Upperville vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Upperville?
If you're considering a spontaneous Upperville trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Upperville?

  1. Choose your dates: The things you'd like to do in Upperville and your favourite season will help you decide when to get away.
  2. Budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Upperville.
  3. Work out your trip length: Think about how long you'd like to spend exploring Upperville. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find an Upperville vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.