Middleburg Vacations from $595
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The Latest Middleburg Vacation Packages
- Margaritaville Jacksonville Beach
Oct 15 - Oct 18Margaritaville Jacksonville Beach + Flight
Oceanfront3 nights2.5 star property9.0/10 - Wonderful (4,303 reviews)Roundtrip • Boston (BOS) - Jacksonville (JAX)BOS - JAX • Nonstop JAX - BOS • Nonstop$762$595found 1 day agoper traveler - Amelia by the Sea
Oct 17 - Oct 20Amelia by the Sea + Flight
Fernandina Beach3 nights4.0 star propertyRoundtrip • New York (NYC) - Jacksonville (JAX)JFK - JAX • Nonstop JAX - JFK • Nonstop - Hyatt Regency Jacksonville
Sep 23 - Sep 28Hyatt Regency Jacksonville + Flight
Downtown Jacksonville5 nights4.0 star property9.0/10 - Wonderful (1,752 reviews)"1 day stay . Appreciated toiletries supplied in room since I had left my toothbrush at home.Bathtub could have been cleaner . Overall a good experienced"Reviewed August 7, 2026Roundtrip • Boston (BOS) - Jacksonville (JAX)BOS - JAX • 1 stop JAX - BOS • 1 stop - Island Oaks RV Resort
Sep 8 - Sep 13Island Oaks RV Resort + Flight
Glen St. Mary5 nights4.0 star property9.2/10 - Wonderful (40 reviews)"Clean area, fun activities, great stay!"Reviewed August 2, 2026Roundtrip • Boston (BOS) - Jacksonville (JAX)BOS - JAX • Nonstop JAX - BOS • 1 stop$904$704found 6 hours agoper traveler - Hammock Beach Golf Resort & Spa
Sep 10 - Sep 13Hammock Beach Golf Resort & Spa + Flight
Palm Coast3 nights4.0 star property8.8/10 - Excellent (1,007 reviews)"We loved our stay at Hammock Beach Resort! We will absolutely go back many more times."Reviewed August 6, 2026Roundtrip • Philadelphia (PHL) - Jacksonville (JAX)PHL - MCO • Nonstop MCO - PHL • Nonstop
What to do in Middleburg
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports
Middleburg Hotel Deals
Hampton Inn & Suites Middleburg
Hampton Inn & Suites Middleburg
TownePlace Suites by Marriott Middleburg
TownePlace Suites by Marriott Middleburg"Currently limited parking. Staff was excellent! Terrance and Jackie were so helpful and kind to us at breakfast. Really was accommodating to the grandchildren."
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
Holiday Inn Express & Suites Fleming Island by IHG
Holiday Inn Express & Suites Fleming Island by IHG
Country Inn & Suites by Radisson, Jacksonville - Orange Park
Country Inn & Suites by Radisson, Jacksonville - Orange Park"The bathroom"
Fairfield Inn by Marriott Jacksonville Orange Park
Fairfield Inn by Marriott Jacksonville Orange Park"Our room was clean. Breakfast was good and the lady working breakfast was very helpful."
Hampton Inn & Suites Jacksonville / Orange Park
Hampton Inn & Suites Jacksonville / Orange Park
Courtyard Jacksonville Orange Park
Courtyard Jacksonville Orange Park"Hi"
Frequently Asked Questions
How much does a Middleburg vacation package cost?
You can snap up a vacation package to this top destination from $595 on Expedia. But how much your vacation to Middleburg costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Middleburg?
You can usually find lower prices and better availability in December, January and February. Explore our cheap Middleburg vacation packages and you could score some excellent off-season deals.
How many days is enough for Middleburg?
Usually, a handful of days is enough to see the top attractions during your Middleburg vacation. But if you prefer to have time to unwind or take day tours, think about extending your trip.
How to find the best Middleburg package deals?
Use Expedia's filters to help you find some of the best Middleburg package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Middleburg package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middleburg vacation as a package?
You can enjoy significant savings on your Middleburg getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Middleburg?
If you're considering a spur-of-the-moment Middleburg trip, check out 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 find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Middleburg vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Middleburg trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.