Middleburg Vacations from $439

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Middleburg vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
Downtown Jacksonville
Price was $583, price is now $439 per person
$439
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
6.8/10 (1,427 reviews)
Parking is very expensive. My 1st room had no refrigerator or microwave, but they made it up with my 2nd beautiful room. There were stains in the carpet and a mess in the elevator but the views and space is amazing depending on the room you get.

Reviewed on Jan 27, 2026

Amelia by the South

Amelia by the South

4 out of 5
Save 100% on your flight
Price was $6,763, price is now $4,518 per person
$4,518
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Amelia by the Sea

Amelia by the Sea

4 out of 5
Save 100% on your flight
Price was $6,790, price is now $4,545 per person
$4,545
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Landing Apartments Jacksonville - Downtown Saint Johns

Landing Apartments Jacksonville - Downtown Saint Johns

4 out of 5
Save 100% on your flight
Price was $739, price is now $549 per person
$549
per person
Mar 13 - Mar 16
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
No reviews
Jekyll Ocean Club

Jekyll Ocean Club

4 out of 5
Beach Village
Save 100% on your flight
Price was $1,722, price is now $1,298 per person
$1,298
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
9.4/10 Exceptional! (229 reviews)
Staff were fantastic. Restaurant food was delicious. Room was nice, but the bed mattress was way to old and very uncomfortable. They need to be replaced!

Reviewed on Nov 23, 2025

Don't see what you're looking for?
See all available trips from Columbus to Middleburg
View all trips

Middleburg Hotel Deals

TownePlace Suites by Marriott Middleburg

TownePlace Suites by Marriott Middleburg

2.5 out of 5
1625 JEREMIAH ST Middleburg FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Feb 8 to Feb 9
$150 total
Feb 8 - Feb 9
Total with taxes and fees
9.8/10 Exceptional! (46 reviews)
Clean, quiet and nice staff

Reviewed on Jan 27, 2026

TownePlace Suites by Marriott Middleburg
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr Jacksonville FL
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $228 total per night from Feb 10 to Feb 11
$228 total
Feb 10 - Feb 11
Total with taxes and fees
8.8/10 Excellent! (1,446 reviews)
Mr. Yancy at the front desk. He was excellent. Very nice and polite. I will be back to stay again.

Reviewed on Jan 25, 2026

Hyatt Regency Jacksonville
Southbank Hotel by Marriott Jacksonville Riverwalk

Southbank Hotel by Marriott Jacksonville Riverwalk

3.5 out of 5
1515 Prudential Dr Jacksonville FL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $132 total per night from Feb 22 to Feb 23
$132 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,642 reviews)
Hotel very nice, and clean! Two guys at the bar (bartenders) were Awesome, very friendly, and attentive. Bar area was full of people socializing, but the guys kept the drinks & music flowing with a smile. They made are stay enjoyable

Reviewed on Jan 30, 2026

Southbank Hotel by Marriott Jacksonville Riverwalk
See all 1,828 properties in 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.

Find the Best Middleburg Vacation Packages

Middleburg Essential Information

Language
English
Currency
U.S dollars
Population
13,000
Max Temp Winter
70ºF
Max Temp Summer
95ºF
Top Sights
Spring Park and Clay County Fairgrounds

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middleburg vacation package cost?
You can snap up a vacation package to this top destination from $439 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.

Explore a world of travel with Expedia

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