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A sunset over a calm lake with a dock and boats.

Middleburg Vacations from $749

Book a Hotel + Flight or Car together to unlock savings

The Latest Middleburg Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Indoor pool, 9 outdoor pools, pool umbrellas, sun loungers
    Sep 10 - Sep 13

    Hammock Beach Golf Resort & Spa + Flight

    Palm Coast
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,009 reviews)
    "The hotel grounds are beautiful and great location on the beach. The pools were lots of fun. We enjoyed the food and cocktails. The big minuses include the rooms are very old and run down. Our carpet was stained with huge rips and the bathroom floors are grimy. The shower was old and the door didn’t shut properly. Tge other big miss was check in. We arrived at 4:30 pm and had to wait two hours for our room to be ready. We were not offered any drink coupons or anything to make up for it while we..."
    Reviewed July 22, 2026
    Roundtrip • Boston (BOS) - Jacksonville (JAX)
    BOS - JAX • Nonstop JAX - BOS • Nonstop
    $994
    $749
    per traveler
    found 1 day ago
    Hammock Beach Golf Resort & Spa
  • Apartment, 3 Bedrooms, Sea View | Living area | TV
    Sep 7 - Sep 13

    Amelia by the South + Flight

    Fernandina Beach
    6 nights
    4.5 star property
    Roundtrip • Boston (BOS) - Jacksonville (JAX)
    BOS - JAX • 1 stop JAX - BOS • Nonstop
    Save 100% on your flight
    $7,290
    $4,926
    per traveler
    found 1 day ago
    Amelia by the South
  • Apartment, 3 Bedrooms, Balcony, Sea View | Living area
    Sep 7 - Sep 13

    Amelia by the Sea + Flight

    Fernandina Beach
    6 nights
    4.0 star property
    Roundtrip • Boston (BOS) - Jacksonville (JAX)
    BOS - JAX • Nonstop JAX - BOS • 1 stop
    Save 100% on your flight
    $7,336
    $4,964
    per traveler
    found 8 hours ago
    Amelia by the Sea
  • On the beach, sun loungers, beach umbrellas, beach towels
    Oct 1 - Oct 6

    Jekyll Ocean Club + Flight

    Beach Village
    5 nights
    4.0 star property
    9.4/10 - Exceptional (250 reviews)
    "Great property to spend a few days"
    Reviewed July 11, 2026
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - JAX • 1 stop JAX - EWR • 1 stop
    Save 100% on your flight
    $1,580
    $1,153
    per traveler
    found 23 hours ago
    Jekyll Ocean Club
  • Exterior
    Oct 1 - Oct 6

    Jekyll Island Club Resort + Flight

    Historic District
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "A great resort with charm and felt transported to a time in the past. Ambience was excellent as were the amenities. The only negative that prevented me from giving a perfect score was the water pressure in the shower and poor drainage in the shower. Otherwise, I would come again."
    Reviewed July 21, 2026
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - JAX • 1 stop JAX - EWR • 1 stop
    Save 100% on your flight
    $1,056
    $786
    per traveler
    found 23 hours ago
    Jekyll Island Club Resort

What to do in Middleburg

1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

$160
per traveler
90% of travelers recommend
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports
See all activities in Middleburg

Middleburg Hotel Deals

Exterior

Hampton Inn & Suites Middleburg

Hampton Inn & Suites Middleburg
2.5 star property
3.4 mi from Middleburg
9.4 out of 10, Exceptional, (694 reviews)
"This hotel was perfect for us. The rooms were immaculate and we appreciated the modern technology. I don’t know what coffee you use, but it’s delicious!! Don’t change it! I want to give a special shout out to Lindsey. She’s a gem! We flew in from Chicago for one night to attend a young boy’s funeral so our trip was not for pleasure. I had called the hotel after we landed in Jacksonville to see if we could check in early to change for the funeral and she was so nice to me. She was happy to...
$118 nightly
The price is $133
Aug 2 - Aug 3
Total with taxes and fees
Hampton Inn & Suites Middleburg
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.
See all properties in Middleburg

Frequently Asked Questions

How much does a Middleburg vacation package cost?

You can snap up a vacation package to this top destination from $749 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.

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