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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Jul. 23 - Jul. 28
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.2/10 Very Good! (601 reviews)
Nobody said that parking is not free.

Reviewed on Apr. 30, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul. 23 - Jul. 28
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9/10 Wonderful! (1,008 reviews)
Large water bug/cockroach in our shower. Staff was responsive and removed it. Worst shower pressure EVER!! Felt like I was not clean after the shower. I will not be returning.

Reviewed on Apr. 27, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Jul. 23 - Jul. 28
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.4/10 Very Good! (1,874 reviews)
Hotel was convienient to all attractions. Limited supplies in the room we needed additional towels and washcloths and could not get anyone on the phone to bring to us. Husband went to lobby and got one, only to be taken away in the morning cleaning and not replaced. Also thought the charge for food each day was a bit sketchy - we did not use it nor wanted it. Price was less per night only to be inflated with surcharges making it the same price as other hotels.

Reviewed on Apr. 28, 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jul. 23 - Jul. 28
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (2,353 reviews)
Front desk personnel were very nice and helpful

Reviewed on Apr. 30, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Jul. 23 - Jul. 28
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
I liked the location of the property, and the fact that it had a pool for my granddaughter. In fact, this combination was why I chose it, despite the price. The staff was all very pleasant. The food was good, but quite pricey.

Reviewed on Apr. 30, 2025

Ready to book your vacation to Upperville?

 

Choose your dates

Upperville Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from May 4 to May 5
CA $129
CA $141 total
includes taxes & fees
May 4 - May 5
9/10 Wonderful! (1,970 reviews)
"I like being near Chinatown and near old town Winchester"

Reviewed on Apr. 26, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 $301 per night from May 11 to May 12
CA $301
CA $394 total
includes taxes & fees
May 11 - May 12
8.6/10 Excellent! (1,000 reviews)
"Such a relaxing stay!"

Reviewed on Apr. 27, 2025

Lansdowne Resort and Spa
Salamander Resort And Spa
Salamander Resort And Spa
5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $768 per night from May 1 to May 2
CA $768
CA $947 total
includes taxes & fees
May 1 - May 2
9/10 Wonderful! (351 reviews)
"This was the best hotel experience we have ever had. Staff went out of their way to be accommodating without you even having to ask for help. We visited for the first time to celebrate our mini moon a free our wedding and they gave us a free room upgrade to a suite. They also surprised us with a ..."

Reviewed on Apr. 29, 2025

Salamander Resort And Spa
See all 689 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 $815 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.