Middleburg 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 Middleburg Vacation
With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.
Ready to book your vacation to Middleburg?
Middleburg Hotel Deals
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
CA $1,014
CA $1,234 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (411 reviews)
"A really luxe resort. Outside pool area super good fun and great for kids and adults alike with separate areas. Well staffed in all areas of the hotel"
Reviewed on Aug 18, 2026
The Red Fox Inn & Tavern
2 E Washington St Middleburg VA
CA $562
CA $641 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (451 reviews)
"Great experience."
Reviewed on Aug 13, 2026
Goodstone Inn & Restaurant
36205 Snake Hill Road Middleburg VA
CA $561
CA $824 total
Aug 27 - Aug 28
includes taxes & fees
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.
Stay near popular Middleburg attractions
Red Fox Fine Art
9.6/10 (10 reviews)
You can spend an afternoon studying the exhibits at Red Fox Fine Art during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
Glenwood Park
10.0/10 (2 reviews)
Explore the great outdoors at Glenwood Park, a lovely green space in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
Greenhill Winery & Vineyards
9.4/10 (28 reviews)
You can enjoy a tasting or tour at Greenhill Winery & Vineyards during your travels to Middleburg. Discover the bars and entertainment venues in this trendy area.
Middleburg Historic District
10.0/10 (1 review)
You can learn about the history of Middleburg with a trip to Middleburg Historic District.
Chrysalis Vineyards
8.4/10 (9 reviews)
You can enjoy a tasting or tour at Chrysalis Vineyards during your travels to Middleburg. While in this trendy area, you can savor the top-notch restaurants.
Cana Vineyards and Winery
7.8/10 (14 reviews)
You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Dover. While in this trendy area, you can savor the top-notch restaurants.
Middleburg Community Center
Find out about the history of Middleburg when you take a trip to Middleburg Community Center.
National Sporting Library & Museum
9.8/10 (8 reviews)
You can spend an afternoon exploring the galleries in National Sporting Library & Museum during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.
What to do in Middleburg
3 VA Wineries Day Trip with Optional Tasting-Inclusive Upgrade
CA $169
per adult
Frequently asked questions
How much does a Middleburg vacation package cost?
You'll find cheap prices on Expedia for your Middleburg escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Middleburg costs.
What are the cheapest months to go to Middleburg?
January, April and September are great times to look for cheap Middleburg vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Middleburg?
When planning your Middleburg vacation, a handful of days will be enough to see the best spots. Make sure to check out Chrysalis Vineyards — it's one of the most popular attractions in this destination. If you're after more activities, consider basing yourself here and venturing off on some day tours from Middleburg.
Is it worth booking a vacation package to Middleburg?
It's easy to see why a Middleburg vacation is on the must-do list of many travellers. Well-known attractions like Glenwood Park are just the beginning of things to keep you busy here.
How to find the best Middleburg package deals?
Landing a cheap Middleburg package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Middleburg package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Middleburg vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Middleburg vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Middleburg?
If you're planning an impromptu Middleburg vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Middleburg?
- Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Middleburg.
- Set a budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Middleburg. Then, pick a property that matches your budget, whether that's an economical stay or a lavish retreat.
- Decide how many days away: Start by compiling a list of the attractions you want to experience in Middleburg. Then, estimate how long you'll need at each, along with any travel time.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Middleburg vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
